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Search for "poly(ethylene glycol)" in Full Text gives 50 result(s) in Beilstein Journal of Organic Chemistry.
Chemoenzymatic synthesis of macrocyclic peptides and polyketides via thioesterase-catalyzed macrocyclization
- Senze Qiao,
- Zhongyu Cheng and
- Fuzhuo Li
Beilstein J. Org. Chem. 2024, 20, 721–733, doi:10.3762/bjoc.20.66
- and promote the utilization of TE domains as biocatalysts with tremendous potential. To this purpose, Walsh and co-workers developed the 2nd generation of tyrocidine chemoenzymatic approach utilizing a linear peptide immobilized on the solid-phase support poly(ethylene glycol) acrylate (PEGA) with a
Graphical Abstract
Scheme 1: Brief introduction of thioesterase (TE) domain. (a) NRPS and PKS assembly lines. (b) Mechanism of T...
Scheme 2: Chemoenzymatic synthesis of tyrocidine A and its analogs. (a) First-gen chemoenzymatic synthesis of...
Scheme 3: Representative examples of NAC-activated thioesters-mediated biocatalytic macrolactamization.
Scheme 4: Chemoenzymatic synthesis of CDA, daptomycin and their analogs. (a) Biocatalytic macrocyclization of...
Scheme 5: Chemoenzymatic synthesis of surugamide B and related natural products. (a) Three synthetic strategi...
Scheme 6: Chemoenzymatic synthesis of the pikromycins. (a) Macrocyclization of 10-deoxymethynolide catalyzed ...
Scheme 7: Chemoenzymatic synthesis of the juevnimicins.
Scheme 8: Chemoenzymatic synthesis of the cryptophycins.
Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles
- Periklis X. Kolagkis,
- Eirini M. Galathri and
- Christoforos G. Kokotos
Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36
- , depending on the substrate used, with both aromatic and aliphatic aldehydes reaching conversion rates of 98% (Scheme 23). In 2021, a methodology making use of poly(ethylene glycol)-supported Fe3O4 nanoparticles was reported by Mardani et al., who managed to remove the need for conventional heating. 10 mg of
Graphical Abstract
Scheme 1: Examples of BIMs used for their medicinal properties.
Scheme 2: Mechanisms for the synthesis of BIMs using protic or Lewis acids as catalysts.
Scheme 3: Synthesis of bis(indolyl)methanes using DBDMH.
Scheme 4: Competition experiments and synthesis of bis(indolyl)methanes using DBDMH.
Scheme 5: Proposed mechanism for formation of BIM of using DBDMH.
Scheme 6: Synthesis of bis(indolyl)methanes using I2.
Scheme 7: General reaction mechanism upon halogen bonding.
Scheme 8: Synthesis of bis(indolyl)methanes using I2, introduced by Ji.
Scheme 9: Synthesis of bis(indolyl)methanes using Br2 in CH3CN.
Scheme 10: Βidentate halogen-bond donors.
Scheme 11: Synthesis of bis(indolyl)methanes using bidentate halogen-bond donor 26.
Scheme 12: Proposed reaction mechanism.
Scheme 13: Synthesis of bis(indolyl)methanes using iodoalkyne as catalyst.
Scheme 14: Proposed reaction mechanism.
Scheme 15: Optimized reaction conditions used by Ramshini.
Scheme 16: Activation of the carbonyl group by HPA/TPI-Fe3O4.
Scheme 17: Synthesis of BIMs in the presence of nanoAg-Pt/SiO2-doped silicate.
Scheme 18: Mechanism of action proposed by Khalafi-Nezhad et al.
Scheme 19: Activation of the carbonyl group by the Cu–isatin Schiff base complex.
Scheme 20: Optimum reaction conditions published by Jain.
Scheme 21: Organocatalytic protocol utilizing nanoparticles introduced by Bankar.
Scheme 22: Activation of the carbonyl group by the AlCl3·6H2O-SDS-SiO2 complex.
Scheme 23: Optimal reaction conditions for the aforementioned nano-Fe3O4 based catalysts.
Scheme 24: Nanocatalytic protocol proposed by Kaur et al.
Scheme 25: Microwave approach introduced by Yuan.
Scheme 26: Microwave approach introduced by Zahran et al.
Scheme 27: Microwave irradiation protocol introduced by Bindu.
Scheme 28: Silica-supported microwave irradiation protocol.
Scheme 29: Proposed mechanism for formation of BIM by Nongkhlaw.
Scheme 30: Microwave-assisted synthesis of BIMs catalyzed by succinic acid.
Scheme 31: Proposed mechanism of action of MMO-4.
Scheme 32: Catalytic approach introduced by Muhammadpoor-Baltork et al.
Scheme 33: Reaction conditions used by Xiao-Ming.
Scheme 34: Ultrasonic irradiation-based protocol published by Saeednia.
Scheme 35: Pyruvic acid-mediated synthesis of BIMs proposed by Thopate.
Scheme 36: Synthesis of BIMs using [bmim]BF4 or [bmim]PF6 ionic liquids.
Scheme 37: Synthesis of BIMs utilizing In(OTf)3 in octylmethylimidazolium hexafluorophosphate as ionic liquid.
Scheme 38: FeCl3·6H2O-catalyzed synthesis of BIMs with use of ionic liquid.
Scheme 39: Synthesis of BIMs utilizing the [hmim]HSO4/EtOH catalytic system.
Scheme 40: Synthesis of BIMs utilizing acidic ionic liquid immobilized on silica gel (ILIS-SO2Cl).
Scheme 41: The [bmim][MeSO4]-catalyzed reaction of indole with various aldehydes.
Scheme 42: The role of [bmim][MeSO4] in catalyzing the reaction of indole with aldehydes.
Scheme 43: Synthesis of BIMs utilizing FeCl3-based ionic liquid ([BTBAC]Cl-FeCl3) as catalyst.
Scheme 44: Synthesis of BIMs using [Msim]Cl at room temperature.
Scheme 45: [Et3NH][H2PO4]-catalyzed synthesis of bis(indolyl)methanes.
Scheme 46: PILs-catalyzed synthesis of bis(indolyl)methanes.
Scheme 47: FSILs-mediated synthesis of bis(indolyl)methanes.
Scheme 48: Possible “release and catch” catalytic process.
Scheme 49: Synthesis of bis(indolyl)methanes by [DABCO-H][HSO4].
Scheme 50: Synthesis of bis(indolyl)methanes by [(THA)(SO4)].
Scheme 51: Synthesis of BBSI-Cl and BBSI-HSO4.
Scheme 52: Synthesis of BIMs in the presence of BBSI-Cl and BBSI-HSO4.
Scheme 53: Chemoselectivity of the present method.
Scheme 54: Synthesis of BIMs catalyzed by chitosan-supported ionic liquid.
Scheme 55: Proposed mechanism of action of CSIL.
Scheme 56: Optimization of the reaction in DESs.
Scheme 57: Synthesis of BIMs using ChCl/SnCl2 as DES.
Scheme 58: Synthesis of BIMs derivatives in presence of DES.
Scheme 59: BIMs synthesis in choline chloride/urea (CC/U).
Scheme 60: Flow chemistry-based synthesis of BIMs by Ley.
Scheme 61: Flow chemistry-based synthesis of BIMs proposed by Nam et al.
Scheme 62: Amino-catalyzed reaction of indole with propionaldehyde.
Scheme 63: Aminocatalytic synthesis of BIMs.
Scheme 64: Proposed mechanism for the aminocatalytic synthesis of BIMs.
Scheme 65: Enzymatic reaction of indole with aldehydes.
Scheme 66: Proposed mechanism for the synthesis of BIMs catalyzed by TLIM.
Scheme 67: Proposed reaction mechanism by Badsara.
Scheme 68: Mechanism proposed by D’Auria.
Scheme 69: Photoinduced thiourea catalysis.
Scheme 70: Proposed mechanism of photoacid activation.
Scheme 71: Proposed mechanism of action for CF3SO2Na.
Scheme 72: Proposed mechanism for the synthesis of BIMs by Mandawad.
Scheme 73: Proposed mechanism for the (a) acid generation and (b) synthesis of BIMs.
Scheme 74: a) Reaction conditions employed by Khaksar and b) activation of the carbonyl group by HFIP.
Scheme 75: Activation of the carbonyl group by the PPy@CH2Br through the formation of a halogen bond.
Scheme 76: Reaction conditions utilized by Mhaldar et al.
Scheme 77: a) Reaction conditions employed by López and b) activation of the carbonyl group by thiourea.
Scheme 78: Infrared irradiation approach introduced by Luna-Mora and his research group.
Scheme 79: Synthesis of BIMs with the use of the Fe–Zn BMOF.
Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone
- Solomiia Borova and
- Robert Luxenhofer
Beilstein J. Org. Chem. 2023, 19, 217–230, doi:10.3762/bjoc.19.21
- biomedical applications, in particular as an alternative to the hydrophilic poly(ethylene glycol) (PEG), which is the polymer of choice for many biomedical applications due to its high solubility, low cytotoxicity and biocompatibility [3][4][5][6][7][8][9]. However, an ongoing discussion about pre-existing
Graphical Abstract
Figure 1: Schematic representation of the mechanism of the cationic ring-opening polymerization (CROP) of 2-a...
Figure 2: (a) First-order kinetic plot for the 2-ethyl-2-oxazoline ring-opening polymerization in DLG at 90 °...
Figure 3: MALDI-TOF mass spectrometry analysis of the poly(2-ethyl-2-oxazoline) initiated with methyl triflat...
Figure 4: MALDI-TOF mass spectrometry analysis of the poly(2-ethyl-2-oxazoline) initiated with 2-ethyl-3-meth...
Figure 5: Schematic illustration of the side reactions that can occur during the polymerization of 2-alkyl-2-...
Figure 6: Investigation of 2-ethyl-2-oxazoline polymerization in DLG at 60 °C initiated with MeOTf (black), M...
Figure 7: Investigation of 2-ethyl-2-oxazoline polymerization initiated with EtOxMeOTf at different monomer/i...
Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing
- Luke O. Jones,
- Leah Williams,
- Tasmin Boam,
- Martin Kalmet,
- Chidubem Oguike and
- Fiona L. Hatton
Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171
- biopolymeric cryogel DDS. Human mesenchymal stromal cells (MSCs) were gene-modified to secrete anti-CD33-anti-CD3 bispecific antibodies (bsAb) to be used for the treatment of acute myeloid leukaemia (AML). Macroporous star-shaped poly(ethylene glycol) (starPEG)-heparin cryogels were prepared by combining
Graphical Abstract
Figure 1: Schematic representation of the process of aqueous cryogel formation, using (a) monomers/small mole...
Figure 2: Microarchitecture of gelatin cryogels. (A) Surface and cross-sectional SEM micrographs of highly po...
Figure 3: Principle of 3D-cryogel printing. A) Illustration of 3D-printing of cryogels. B) Illustration of th...
Figure 4: Illustration of the production of the injectable multifunctional composite, comprised of alginate c...
Figure 5: Digital and SEM photographs of PETEGA cryogel at 20 °C (top) and 50 °C (bottom), synthesised via UV...
Figure 6: Cell morphology of T47D breast cancer cells cultured in HA cryogels. (A) Schematic representation o...
Figure 7: Preparation of PDMA/β-CD cryogel via cryogenic treatment and photochemical crosslinking in frozen s...
Figure 8: (A) Healing rate of wounds treated with autoclaved CG11 cryogels and those treated with 70% ethanol...
Figure 9: In vivo haemostatic capacity evaluation of the cryogels. Blood loss (a) and haemostatic time (b) in...
In-depth characterization of self-healing polymers based on π–π interactions
- Josefine Meurer,
- Julian Hniopek,
- Johannes Ahner,
- Michael Schmitt,
- Jürgen Popp,
- Stefan Zechel,
- Kalina Peneva and
- Martin D. Hager
Beilstein J. Org. Chem. 2021, 17, 2496–2504, doi:10.3762/bjoc.17.166
- molar mass of approximately 2000 g/mol resulting in polymer P1. In order to study the influence of the polymer backbone on the material’s properties, the diamine containing polymer was exchanged to a triblock copolymer of poly(propylene glycol)-block-poly(ethylene glycol)-block-poly(propylene glycol
- , polymer P2 could not be damaged in a sufficient manner (under the utilized conditions) due to the polymer design. In particular, the poly(ethylene glycol) block resulted in a sufficient elastic recovery. Consequently, the material could not be analyzed via scratch testing in sufficient manner. The current
- (degasser), LC-20AD (pump), SIL-20AHT (auto sampler), CTO-10AC vp (oven), SPD-20A (UV detector), RID-10A (RI detector), PSS SDV guard/1000 Å/1,000,000 Å (5 μm particle size) chloroform/isopropanol/triethylamine [94/2/4] with 1 mL/ min at 40 °C, poly(ethylene glycol) (standard). Differential scanning
Graphical Abstract
Scheme 1: Schematic representation of the polymer synthesis of P1 and P2.
Figure 1: DSC-analysis of the polymers P1 and P2 (second heating and cooling cycle; 20 K/min for heating and ...
Figure 2: DMTA analysis of P1 and P2 showing the transition at around 130 °C due to the reversible π–π intera...
Figure 3: Frequency sweeps of polymers P1 (left) and P2 (right).
Figure 4: Temperature dependent IR spectra of P1 drop casted on KBr in the C=C (1570–1605 cm−1) and C=O stret...
Figure 5: Schematic representation of the first healing of P1 at 150 °C.
Post-functionalization of drug-loaded nanoparticles prepared by polymerization-induced self-assembly (PISA) with mitochondria targeting ligands
- Janina-Miriam Noy,
- Fan Chen and
- Martina Stenzel
Beilstein J. Org. Chem. 2021, 17, 2302–2314, doi:10.3762/bjoc.17.148
- nanoparticles without TPP have been reported earlier [42]. This figure was adapted with permission from [42], Noy et al., Direct Comparison of Poly(ethylene glycol) and Phosphorylcholine Drug-Loaded Nanoparticles In Vitro and In Vivo, Biomacromolecules 2020, 21, 2320–2333. Copyright 2020 American Chemical
- MPM-NP2-TPP on SW982 cells in relation to the concentration of PENAO present. The results of the nanoparticles without TPP have been reported earlier [42]. This figure was adapted with permission from [42], Noy et al., Direct Comparison of Poly(ethylene glycol) and Phosphorylcholine Drug-Loaded
Graphical Abstract
Figure 1: (I) DLS of PPM-NP4, MPM-NP2, PPM-NP4-TPP and MPM-NP2-TPP and (II) TEM of PPM-NP4-TPP and MPM-NP2-TPP...
Figure 2: Representative 31P NMR (top) and 1H NMR (bottom) spectrum of PP3-TPP conjugation product in D2O.
Scheme 1: Synthesis of TPP-based PISA particles based on zwitterionic 2-methacryloyloxyethyl phosphorylcholin...
Figure 3: Penetration of PPM-NP4-TPP and MPM-NP2-TPP micelles and fluorescence intensity profile on (A I, II)...
Figure 4: Growth effects of PPM-NP4-TPP and MPM-NP2-TPP on SW982 spheroids after 3 and 6 days of incubation (c...
Figure 5: Cell viability of SW982 spheroids after 6 days treatment with PPM-NP4, PPM-NP-TPP, MPM-NP2 and MPM-...
Figure 6: Cell localization of PPM-NP4-TPP (I) and MPM-NP2-TPP (II) into (A) mitochondria and (B) lysosomes u...
Figure 7: Cytotoxicity study of PPM-NP4-TPP and MPM-NP2-TPP on SW982 cells in relation to the concentration o...
Constrained thermoresponsive polymers – new insights into fundamentals and applications
- Patricia Flemming,
- Alexander S. Münch,
- Andreas Fery and
- Petra Uhlmann
Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138
Graphical Abstract
Figure 1: (a) Schematic representation of the phase stability of a binary mixture based on the free enthalpy ...
Figure 2: Illustration of the relationship between the type of miscibility gap and the temperature dependence...
Figure 3: Schematically pictured phase diagram of a binary mixture composed of a dissolved polymer with a LCS...
Figure 4: Schematic illustration of a thermo-induced swelling behavior of a star polymer composed of responsi...
Figure 5: Schematic illustration of self-assembly of block copolymer amphiphiles in a polar medium.
Figure 6: Schematic comparison of the size and conformation between free polymer chains (a), grafted polymer ...
Figure 7: Comparison of the possible phase diagrams of a polymer in solution with partially miscibility and t...
Figure 8: Selection of polymers exhibiting UCST behavior due to hydrogen bonding (blue) divided into homo- (a...
Figure 9: Part A shows the molecular structure of PDMAPS stars synthesized by Li et al. (left) demonstrating ...
Figure 10: Part A contains a schematic demonstration of conformational transitions of dual-thermoresponsive bl...
Figure 11: Part A pictures zwitterionic brushes grafted from silicon substrates obtaining a nonassociated, hyd...
Figure 12: Part A pictures the UCST phase transition of zwitterionic polymers grafted on the surface of mesopo...
Photoinduced post-modification of graphitic carbon nitride-embedded hydrogels: synthesis of 'hydrophobic hydrogels' and pore substructuring
- Cansu Esen and
- Baris Kumru
Beilstein J. Org. Chem. 2021, 17, 1323–1334, doi:10.3762/bjoc.17.92
- primary amide C=O stretching vibration of the amide group. The strong signals at 1558 and 1404 cm−1 are originated from amine N–H bending and scissoring –CH2– vibrations, respectively. At last, the poly(ethylene glycol) methyl ether methacrylate (PEGMEMA)-based network displays O–H stretching from 3106 cm
- % aqueous solution, Merck), magnesium chloride (MgCl2, 99%, Merck), melamine (99%, Sigma-Aldrich), poly(ethylene glycol) dimethacrylate (PEGDMA, Mn 550, Sigma-Aldrich), poly(ethylene glycol) methyl ether methacrylate (PEGMEMA, Mn 300, Sigma-Aldrich), potassium chloride (KCl, 99%, Merck), rhodamine B (RhB
Graphical Abstract
Scheme 1: Schematic overview of g-CN-embedded hydrogel fabrication and its subsequent photoinduced post-modif...
Scheme 2: Hydrophobic hydrogel via photoinduced surface modification over embedded g-CN nanosheets in hydroge...
Figure 1: a) FTIR spectra of freeze-dried HGCM-vTA, HGCM and HG. b) UV spectra of freeze-dried HGCM-vTA, HGCM...
Figure 2: Scanning electron microscopy (SEM) images of a) HGCM and b) HGCM-vTA in combination with their elem...
Figure 3: a) Equilibrium swelling ratios of HG, HGCM, HGCM-vTA at specified time intervals. b) Thermogravimet...
Scheme 3: Overview of pore substructuring via photoinduced free radical polymerization over embedded g-CN nan...
Figure 4: FTIR spectra of freeze-dried HGCM-PAA, HGCM-PAAM, HGCM-PEGMEMA in comparison with HGCM.
Figure 5: Scanning electron microscopy (SEM) images of a) HGCM-PAA, b) HGCM-PAAM, and c) HGCM-PEGMEMA.
Figure 6: a) Thermogravimetric analysis of HGCM, HGCM-PAA, HGCM-PAAM and HGCM-PEGMEMA. b) Equilibrium swellin...
A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries
- Guido Gambacorta,
- James S. Sharley and
- Ian R. Baxendale
Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90
Graphical Abstract
Figure 1: Representative shares of the global F&F market (2018) segmented on their applications [1].
Figure 2: General structure of an international fragrance company [2].
Figure 3: The Michael Edwards fragrance wheel.
Figure 4: Examples of oriental (1–3), woody (4–7), fresh (8–10), and floral (11 and 12) notes.
Figure 5: A basic depiction of batch vs flow.
Scheme 1: Examples of reactions for which flow processing outperforms batch.
Scheme 2: Some industrially important aldol-based transformations.
Scheme 3: Biphasic continuous aldol reactions of acetone and various aldehydes.
Scheme 4: Aldol synthesis of 43 in flow using LiHMDS as the base.
Scheme 5: A semi-continuous synthesis of doravirine (49) involving a key aldol reaction.
Scheme 6: Enantioselective aldol reaction using 5-(pyrrolidin-2-yl)tetrazole (51) as catalyst in a microreact...
Scheme 7: Gröger's example of asymmetric aldol reaction in aqueous media.
Figure 6: Immobilised reagent column reactor types.
Scheme 8: Photoinduced thiol–ene coupling preparation of silica-supported 5-(pyrrolidin-2-yl)tetrazole 63 and...
Scheme 9: Continuous-flow approach for enantioselective aldol reactions using the supported catalyst 67.
Scheme 10: Ötvös’ employment of a solid-supported peptide aldol catalyst in flow.
Scheme 11: The use of proline tetrazole packed in a column for aldol reaction between cyclohexanone (65) and 2...
Scheme 12: Schematic diagram of an aminosilane-grafted Si-Zr-Ti/PAI-HF reactor for continuous-flow aldol and n...
Scheme 13: Continuous-flow condensation for the synthesis of the intermediate 76 to nabumetone (77) and Microi...
Scheme 14: Synthesis of ψ-Ionone (80) in continuous-flow via aldol condensation between citral (79) and aceton...
Scheme 15: Synthesis of β-methyl-ionones (83) from citral (79) in flow. The steps are separately described, an...
Scheme 16: Continuous-flow synthesis of 85 from 84 described by Gavriilidis et al.
Scheme 17: Continuous-flow scCO2 apparatus for the synthesis of 2-methylpentanal (87) and the self-condensed u...
Scheme 18: Chen’s two-step flow synthesis of coumarin (90).
Scheme 19: Pechmann condensation for the synthesis of 7-hydroxyxcoumarin (93) in flow. The setup extended to c...
Scheme 20: Synthesis of the dihydrojasmonate 35 exploiting nitro derivative proposed by Ballini et al.
Scheme 21: Silica-supported amines as heterogeneous catalyst for nitroaldol condensation in flow.
Scheme 22: Flow apparatus for the nitroaldol condensation of p-hydroxybenzaldehyde (102) to nitrostyrene 103 a...
Scheme 23: Nitroaldol reaction of 64 to 105 employing a quaternary ammonium functionalised PANF.
Scheme 24: Enantioselective nitroaldol condensation for the synthesis of 108 under flow conditions.
Scheme 25: Enatioselective synthesis of 1,2-aminoalcohol 110 via a copper-catalysed nitroaldol condensation.
Scheme 26: Examples of Knoevenagel condensations applied for fragrance components.
Scheme 27: Flow apparatus for Knoevenagel condensation described in 1989 by Venturello et al.
Scheme 28: Knoevenagel reaction using a coated multichannel membrane microreactor.
Scheme 29: Continuous-flow apparatus for Knoevenagel condensation employing sugar cane bagasse as support deve...
Scheme 30: Knoevenagel reaction for the synthesis of 131–135 in flow using an amine-functionalised silica gel. ...
Scheme 31: Continuous-flow synthesis of compound 137, a key intermediate for the synthesis of pregabalin (138)...
Scheme 32: Continuous solvent-free apparatus applied for the synthesis of compounds 140–143 using a TSE. Throu...
Scheme 33: Lewis et al. developed a spinning disc reactor for Darzens condensation of 144 and a ketone to furn...
Scheme 34: Some key industrial applications of conjugate additions in the F&F industry.
Scheme 35: Continuous-flow synthesis of 4-(2-hydroxyethyl)thiomorpholine 1,1-dioxide (156) via double conjugat...
Scheme 36: Continuous-flow system for Michael addition using CsF on alumina as the catalyst.
Scheme 37: Calcium chloride-catalysed asymmetric Michael addition using an immobilised chiral ligand.
Scheme 38: Continuous multistep synthesis for the preparation of (R)-rolipram (173). Si-NH2: primary amine-fun...
Scheme 39: Continuous-flow Michael addition using ion exchange resin Amberlyst® A26.
Scheme 40: Preparation of the heterogeneous catalyst 181 developed by Paixão et al. exploiting Ugi multicompon...
Scheme 41: Continuous-flow system developed by the Paixão’s group for the preparation of Michael asymmetric ad...
Scheme 42: Continuous-flow synthesis of nitroaldols catalysed by supported catalyst 184 developed by Wennemers...
Scheme 43: Heterogenous polystyrene-supported catalysts developed by Pericàs and co-workers.
Scheme 44: PANF-supported pyrrolidine catalyst for the conjugate addition of cyclohexanone (65) and trans-β-ni...
Scheme 45: Synthesis of (−)-paroxetine precursor 195 developed by Ötvös, Pericàs, and Kappe.
Scheme 46: Continuous-flow approach for the 5-step synthesis of (−)-oseltamivir (201) as devised by Hayashi an...
Scheme 47: Continuous-flow enzyme-catalysed Michael addition.
Scheme 48: Continuous-flow copper-catalysed 1,4 conjugate addition of Grignard reagents to enones. Reprinted w...
Scheme 49: A collection of commonly encountered hydrogenation reactions.
Figure 7: The ThalesNano H-Cube® continuous-flow hydrogenator.
Scheme 50: Chemoselective reduction of an α,β-unsaturated ketone using the H-Cube® reactor.
Scheme 51: Incorporation of Lindlar’s catalyst into the H-Cube® reactor for the reduction of an alkyne.
Scheme 52: Continuous-flow semi-hydrogenation of alkyne 208 to 209 using SACs with H-Cube® system.
Figure 8: The standard setups for tube-in-tube gas–liquid reactor units.
Scheme 53: Homogeneous hydrogenation of olefins using a tube-in-tube reactor setup.
Scheme 54: Recyclable heterogeneous flow hydrogenation system.
Scheme 55: Leadbeater’s reverse tube-in-tube hydrogenation system for olefin reductions.
Scheme 56: a) Hydrogenation using a Pd-immobilised microchannel reactor (MCR) and b) a representation of the i...
Scheme 57: Hydrogenation of alkyne 238 exploiting segmented flow in a Pd-immobilised capillary reactor.
Scheme 58: Continuous hydrogenation system for the preparation of cyrene (241) from (−)-levoglucosenone (240).
Scheme 59: Continuous hydrogenation system based on CSMs developed by Hornung et al.
Scheme 60: Chemoselective reduction of carbonyls (ketones over aldehydes) in flow.
Scheme 61: Continuous system for the semi-hydrogenation of 256 and 258, developed by Galarneau et al.
Scheme 62: Continuous synthesis of biodiesel fuel 261 from lignin-derived furfural acetone (260).
Scheme 63: Continuous synthesis of γ-valerolacetone (263) via CTH developed by Pineda et al.
Scheme 64: Continuous hydrogenation of lignin-derived biomass (products 265, 266, and 267) using a sustainable...
Scheme 65: Ru/C or Rh/C-catalysed hydrogenation of arene in flow as developed by Sajiki et al.
Scheme 66: Polysilane-immobilized Rh–Pt-catalysed hydrogenation of arenes in flow by Kobayashi et al.
Scheme 67: High-pressure in-line mixing of H2 for the asymmetric reduction of 278 at pilot scale with a 73 L p...
Figure 9: Picture of the PFR employed at Eli Lilly & Co. for the continuous hydrogenation of 278 [287]. Reprinted ...
Scheme 68: Continuous-flow asymmetric hydrogenation using Oppolzer's sultam 280 as chiral auxiliary.
Scheme 69: Some examples of industrially important oxidation reactions in the F&F industry. CFL: compact fluor...
Scheme 70: Gold-catalysed heterogeneous oxidation of alcohols in flow.
Scheme 71: Uozumi’s ARP-Pt flow oxidation protocol.
Scheme 72: High-throughput screening of aldehyde oxidation in flow using an in-line GC.
Scheme 73: Permanganate-mediated Nef oxidation of nitroalkanes in flow with the use of in-line sonication to p...
Scheme 74: Continuous-flow aerobic anti-Markovnikov Wacker oxidation.
Scheme 75: Continuous-flow oxidation of 2-benzylpyridine (312) using air as the oxidant.
Scheme 76: Continuous-flow photo-oxygenation of monoterpenes.
Scheme 77: A tubular reactor design for flow photo-oxygenation.
Scheme 78: Glucose oxidase (GOx)-mediated continuous oxidation of glucose using compressed air and the FFMR re...
Scheme 79: Schematic continuous-flow sodium hypochlorite/TEMPO oxidation of alcohols.
Scheme 80: Oxidation using immobilised TEMPO (344) was developed by McQuade et al.
Scheme 81: General protocol for the bleach/catalytic TBAB oxidation of aldehydes and alcohols.
Scheme 82: Continuous-flow PTC-assisted oxidation using hydrogen peroxide. The process was easily scaled up by...
Scheme 83: Continuous-flow epoxidation of cyclohexene (348) and in situ preparation of m-CPBA.
Scheme 84: Continuous-flow epoxidation using DMDO as oxidant.
Scheme 85: Mukayama aerobic epoxidation optimised in flow mode by the Favre-Réguillon group.
Scheme 86: Continuous-flow asymmetric epoxidation of derivatives of 359 exploiting a biomimetic iron catalyst.
Scheme 87: Continuous-flow enzymatic epoxidation of alkenes developed by Watts et al.
Scheme 88: Engineered multichannel microreactor for continuous-flow ozonolysis of 366.
Scheme 89: Continuous-flow synthesis of the vitamin D precursor 368 using multichannel microreactors. MFC: mas...
Scheme 90: Continuous ozonolysis setup used by Kappe et al. for the synthesis of various substrates employing ...
Scheme 91: Continuous-flow apparatus for ozonolysis as developed by Ley et al.
Scheme 92: Continuous-flow ozonolysis for synthesis of vanillin (2) using a film-shear flow reactor.
Scheme 93: Examples of preparative methods for ajoene (386) and allicin (388).
Scheme 94: Continuous-flow oxidation of thioanisole (389) using styrene-based polymer-supported peroxytungstat...
Scheme 95: Continuous oxidation of thiosulfinates using Oxone®-packed reactor.
Scheme 96: Continuous-flow electrochemical oxidation of thioethers.
Scheme 97: Continuous-flow oxidation of 400 to cinnamophenone (235).
Scheme 98: Continuous-flow synthesis of dehydrated material 401 via oxidation of methyl dihydrojasmonate (33).
Scheme 99: Some industrially important transformations involving Grignard reagents.
Scheme 100: Grachev et al. apparatus for continuous preparation of Grignard reagents.
Scheme 101: Example of fluidized Mg bed reactor with NMR spectrometer as on-line monitoring system.
Scheme 102: Continuous-flow synthesis of Grignard reagents and subsequent quenching reaction.
Figure 10: Membrane-based, liquid–liquid separator with integrated pressure control [52]. Adapted with permission ...
Scheme 103: Continuous-flow synthesis of 458, an intermediate to fluconazole (459).
Scheme 104: Continuous-flow synthesis of ketones starting from benzoyl chlorides.
Scheme 105: A Grignard alkylation combining CSTR and PFR technologies with in-line infrared reaction monitoring....
Scheme 106: Continuous-flow preparation of 469 from Grignard addition of methylmagnesium bromide.
Scheme 107: Continuous-flow synthesis of Grignard reagents 471.
Scheme 108: Preparation of the Grignard reagent 471 using CSTR and the continuous process for synthesis of the ...
Scheme 109: Continuous process for carboxylation of Grignard reagents in flow using tube-in-tube technology.
Scheme 110: Continuous synthesis of propargylic alcohols via ethynyl-Grignard reagent.
Scheme 111: Silica-supported catalysed enantioselective arylation of aldehydes using Grignard reagents in flow ...
Scheme 112: Acid-catalysed rearrangement of citral and dehydrolinalool derivatives.
Scheme 113: Continuous stilbene isomerisation with continuous recycling of photoredox catalyst.
Scheme 114: Continuous-flow synthesis of compound 494 as developed by Ley et al.
Scheme 115: Selected industrial applications of DA reaction.
Scheme 116: Multistep flow synthesis of the spirocyclic structure 505 via employing DA cycloaddition.
Scheme 117: Continuous-flow DA reaction developed in a plater flow reactor for the preparation of the adduct 508...
Scheme 118: Continuous-flow DA reaction using a silica-supported imidazolidinone organocatalyst.
Scheme 119: Batch vs flow for the DA reaction of (cyclohexa-1,5-dien-1-yloxy)trimethylsilane (513) with acrylon...
Scheme 120: Continuous-flow DA reaction between 510 and 515 using a shell-core droplet system.
Scheme 121: Continuous-flow synthesis of bicyclic systems from benzyne precursors.
Scheme 122: Continuous-flow synthesis of bicyclic scaffolds 527 and 528 for further development of potential ph...
Scheme 123: Continuous-flow inverse-electron hetero-DA reaction to pyridine derivatives such as 531.
Scheme 124: Comparison between batch and flow for the synthesis of pyrimidinones 532–536 via retro-DA reaction ...
Scheme 125: Continuous-flow coupled with ultrasonic system for preparation of ʟ-ascorbic acid derivatives 539 d...
Scheme 126: Two-step continuous-flow synthesis of triazole 543.
Scheme 127: Continuous-flow preparation of triazoles via CuAAC employing 546-based heterogeneous catalyst.
Scheme 128: Continuous-flow synthesis of compounds 558 through A3-coupling and 560 via AgAAC both employing the...
Scheme 129: Continuous-flow photoinduced [2 + 2] cycloaddition for the preparation of bicyclic derivatives of 5...
Scheme 130: Continuous-flow [2 + 2] and [5 + 2] cycloaddition on large scale employing a flow reactor developed...
Scheme 131: Continuous-flow preparation of the tricyclic structures 573 and 574 starting from pyrrole 570 via [...
Scheme 132: Continuous-flow [2 + 2] photocyclization of cinnamates.
Scheme 133: Continuous-flow preparation of cyclobutane 580 on a 5-plates photoreactor.
Scheme 134: Continuous-flow [2 + 2] photocycloaddition under white LED lamp using heterogeneous PCN as photocat...
Figure 11: Picture of the parallel tube flow reactor (PTFR) "The Firefly" developed by Booker-Milburn et al. a...
Scheme 135: Continuous-flow acid-catalysed [2 + 2] cycloaddition between silyl enol ethers and acrylic esters.
Scheme 136: Continuous synthesis of lactam 602 using glass column reactors.
Scheme 137: In situ generation of ketenes for the Staudinger lactam synthesis developed by Ley and Hafner.
Scheme 138: Application of [2 + 2 + 2] cycloadditions in flow employed by Ley et al.
Scheme 139: Examples of FC reactions applied in F&F industry.
Scheme 140: Continuous-flow synthesis of ibuprofen developed by McQuade et al.
Scheme 141: The FC acylation step of Jamison’s three-step ibuprofen synthesis.
Scheme 142: Synthesis of naphthalene derivative 629 via FC acylation in microreactors.
Scheme 143: Flow system for rapid screening of catalysts and reaction conditions developed by Weber et al.
Scheme 144: Continuous-flow system developed by Buorne, Muller et al. for DSD optimisation of the FC acylation ...
Scheme 145: Continuous-flow FC acylation of alkynes to yield β-chlorovinyl ketones such as 638.
Scheme 146: Continuous-flow synthesis of tonalide (619) developed by Wang et al.
Scheme 147: Continuous-flow preparation of acylated arene such as 290 employing Zr4+-β-zeolite developed by Kob...
Scheme 148: Flow system applied on an Aza-FC reaction catalysed by the thiourea catalyst 648.
Scheme 149: Continuous hydroformylation in scCO2.
Scheme 150: Two-step flow synthesis of aldehyde 655 through a sequential Heck reaction and subsequent hydroform...
Scheme 151: Single-droplet (above) and continuous (below) flow reactors developed by Abolhasani et al. for the ...
Scheme 152: Continuous hydroformylation of 1-dodecene (655) using a PFR-CSTR system developed by Sundmacher et ...
Scheme 153: Continuous-flow synthesis of the aldehyde 660 developed by Eli Lilly & Co. [32]. Adapted with permissio...
Scheme 154: Continuous asymmetric hydroformylation employing heterogenous catalst supported on carbon-based sup...
Scheme 155: Examples of acetylation in F&F industry: synthesis of bornyl (S,R,S-664) and isobornyl (S,S,S-664) ...
Scheme 156: Continuous-flow preparation of bornyl acetate (S,R,S-664) employing the oscillating flow reactor.
Scheme 157: Continuous-flow synthesis of geranyl acetate (666) from acetylation of geraniol (343) developed by ...
Scheme 158: 12-Ttungstosilicic acid-supported silica monolith-catalysed acetylation in flow.
Scheme 159: Continuous-flow preparation of cyclopentenone 676.
Scheme 160: Two-stage synthesis of coumarin (90) via acetylation of salicylaldehyde (88).
Scheme 161: Intensification process for acetylation of 5-methoxytryptamine (677) to melatonin (678) developed b...
Scheme 162: Examples of macrocyclic musky odorants both natural (679–681) and synthetic (682 and 683).
Scheme 163: Flow setup combined with microwave for the synthesis of macrocycle 686 via RCM.
Scheme 164: Continuous synthesis of 2,5-dihydro-1H-pyrroles via ring-closing metathesis.
Scheme 165: Continuous-flow metathesis of 485 developed by Leadbeater et al.
Figure 12: Comparison between RCM performed using different routes for the preparation of 696. On the left the...
Scheme 166: Continuous-flow RCM of 697 employed the solid-supported catalyst 698 developed by Grela, Kirschning...
Scheme 167: Continuous-flow RORCM of cyclooctene employing the silica-absorbed catalyst 700.
Scheme 168: Continuous-flow self-metathesis of methyl oleate (703) employing SILP catalyst 704.
Scheme 169: Flow apparatus for the RCM of 697 using a nanofiltration membrane for the recovery and reuse of the...
Scheme 170: Comparison of loadings between RCMs performed with different routes for the synthesis of 709.
Synthesis and physicochemical evaluation of fluorinated lipopeptide precursors of ligands for microbubble targeting
- Masayori Hagimori,
- Estefanía E. Mendoza-Ortega and
- Marie Pierre Krafft
Beilstein J. Org. Chem. 2021, 17, 511–518, doi:10.3762/bjoc.17.45
- penetrating properties, such as the transactivator of the transcription (TAT) peptide. Moreover, peptides being smaller than the antibodies generally induce a lower immunogenicity [15][16][17]. Micro- and nanocarriers are often covered by poly(ethylene glycol) (PEG) stealth coatings that significantly enhance
Graphical Abstract
Scheme 1: a) Schematic representation of a perfluorohexane-stabilized microbubble with a fluorinated lipopept...
Scheme 2: Solid-phase synthesis of F-lipopeptides 1–3 and hydrocarbon counterpart 4.
Figure 1: Adsorption kinetics of perfluoroalkylated lipopeptides 1–3 and the hydrocarbon analog 4 at the air/...
Figure 2: Adsorption of perfluoroalkylated lipopeptides 1–3 and hydrocarbon analog 4 on DPPC monolayers sprea...
Figure 3: Optical micrographs and corresponding size distribution of the perfluorohexane-stabilized microbubb...
Figure 4: Half-lives of microbubbles (25 °C) containing F-lipopeptides 1–3 and hydrocarbon analog 4.
Ultrasound-assisted Strecker synthesis of novel 2-(hetero)aryl-2-(arylamino)acetonitrile derivatives
- Emese Gal,
- Luiza Gaina,
- Hermina Petkes,
- Alexandra Pop,
- Castelia Cristea,
- Gabriel Barta,
- Dan Cristian Vodnar and
- Luminiţa Silaghi-Dumitrescu
Beilstein J. Org. Chem. 2020, 16, 2929–2936, doi:10.3762/bjoc.16.242
- trimethylsilyl cyanide (TMSCN) in poly(ethylene glycol) (PEG) solution. The advantages of the sonochemical versus the conventional α-(arylamino)acetonitrile synthesis are the significantly shorter reaction time (30 min instead of 72 hours), the higher purity and the easier separation of the product that
- , ferrocene or benzene units was screened by the Salmonella mutagenicity assay (Ames test) [28] using S. typhimurium TA98 and TA100 strains. Results and Discussions Ultrasound-assisted synthesis The Strecker reaction between (hetero)aromatic aldimines and TMSCN in poly(ethylene glycol) (PEG)–water medium [18
Graphical Abstract
Scheme 1: Synthesis of α-amino-acetonitrile derivatives. Reaction conditions: Aldimine (1 equiv), TMSCN (1 eq...
Figure 1: Crystal structure of 2-phenothiazinyl-2-(p-tolylamino)acetonitrile 2a. a) ORTEP plot and b) crystal...
Figure 2: SEM images recorded at 200× for the raw reaction product 2b obtained through a) ultrasound-assisted...
Figure 3: SEM image recorded at 200× for the raw reaction product 2c obtained through a) ultrasound-assisted ...
Fluorescent phosphorus dendrimers excited by two photons: synthesis, two-photon absorption properties and biological uses
- Anne-Marie Caminade,
- Artem Zibarov,
- Eduardo Cueto Diaz,
- Aurélien Hameau,
- Maxime Klausen,
- Kathleen Moineau-Chane Ching,
- Jean-Pierre Majoral,
- Jean-Baptiste Verlhac,
- Olivier Mongin and
- Mireille Blanchard-Desce
Beilstein J. Org. Chem. 2019, 15, 2287–2303, doi:10.3762/bjoc.15.221
- one case, phenol PEG (poly(ethylene glycol) was grafted together with pyridine imine phenol, affording dendrimers stochastically functionalized on the surface, but all having precisely 12 fluorophores in the internal structure [59]. Another way to induce solubility in water consists in having
Graphical Abstract
Figure 1: Jablonski-type diagram displaying the classical one-photon excited fluorescence (left), and the les...
Figure 2: Two ways to represent schematized structures of dendrimers, showing the different generations (laye...
Scheme 1: Synthesis of phosphorhydrazone dendrimers, from the core to generation 2. Generation 1 dendrimers w...
Scheme 2: Full structure of the generation 1 dendrimer bearing 12 blue-emitting TPA fluorophores on the surfa...
Figure 3: Linear structure of the generation 2 dendrimer bearing 24 green-emitting TPA fluorophores on the su...
Scheme 3: Synthesis of the dioxaborine-functionalized dendrimer of generation 4.
Figure 4: Diverse structures of multistilbazole compounds, and graph of the σ2max/εmax response, depending on...
Figure 5: Nile Red derivatives: monomer (M) and two generations of dendrimers.
Scheme 4: Dumbbell-like dendrimers (third generation) having one TPA fluorophore at the core, and ammonium te...
Scheme 5: Another example of dumbbell-like dendrimers having one TPA fluorophore at the core, and P(S)Cl2 or ...
Scheme 6: The 12 steps needed to synthesize a sophisticated TPA fluorophore, to be used as branches of dendri...
Scheme 7: Synthesis of dendrimers having TPA fluorophores as branches and water-solubilizing functions on the...
Figure 6: Other types of dendrimers having TPA fluorophores as branches and water-solubilizing functions on t...
Figure 7: Generations 0, 1, and 2 of dumbbell-like dendrimers having one fluorophore at the core and either 1...
Figure 8: Double layer fluorescent dendrimer.
Figure 9: Dumbbell-like dendrimer used for two-photon imaging of the blood vessels of a living rat olfactory ...
Figure 10: Fluorescent gold complex having high antiproliferative activities against different tumor cell line...
Figure 11: A fluorescent water-soluble dendrimer, applicable for two-photon photodynamic therapy and imaging.
Figure 12: Schematization of the different types of TPA fluorescent phosphorus dendrimers and dendritic struct...
An overview of the cycloaddition chemistry of fulvenes and emerging applications
- Ellen Swan,
- Kirsten Platts and
- Anton Blencowe
Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209
- [190]. Preparation of hydrogels via Diels–Alder cycloaddition with fulvene-conjugated dextran and dichloromaleic acid-modified poly(ethylene glycol) [191]. Ring-opening metathesis polymerisation of norbornene derivatives derived from fulvenes and maleimides to furnish facially amphiphilic polymers
Graphical Abstract
Figure 1: General structure of fulvenes, named according to the number of carbon atoms in their ring. Whilst ...
Figure 2: Generic structures of commonly referenced heteropentafulvenes, named according to the heteroatom su...
Scheme 1: Resonance structures of (a) pentafulvene and (b) heptafulvene showing neutral (1 and 2), dipolar (1a...
Scheme 2: Resonance structures of (a) pentafulvenes and (b) heptafulvenes showing the influence of EDG and EW...
Scheme 3: Reaction of 6,6-dimethylpentafulvene with singlet state oxygen to form an enol lactone via the mult...
Scheme 4: Photosensitized oxygenation of 8-cyanoheptafulvene with singlet state oxygen to afford 1,4-epidioxi...
Figure 3: A representation of HOMO–LUMO orbitals of pentafulvene and the influence of EWG and EDG substituent...
Scheme 5: Reactions of (a) 6,6-dimethylpentafulvene participating as 2π and 4π components in cycloadditions w...
Scheme 6: Proposed mechanism for the [6 + 4] cycloaddition of tropone with dimethylfulvene via an ambimodal [...
Scheme 7: Triafulvene dimerization through the proposed 'head-to-tail' mechanism. The dipolar transition stat...
Scheme 8: Dimerization of pentafulvenes via a Diels–Alder cycloaddition pathway whereby one fulvene acts as a...
Scheme 9: Dimerization of pentafulvenes via frustrated Lewis pair chemistry as reported by Mömming et al. [116].
Scheme 10: Simplified reaction scheme for the formation of kempane from an extended-chain pentafulvene [127].
Scheme 11: The enantioselective (>99% ee), asymmetric, catalytic, intramolecular [6 + 2] cycloaddition of fulv...
Scheme 12: Intramolecular [8 + 6] cycloaddition of the heptafulvene-pentafulvene derivative [22,27].
Scheme 13: Reaction scheme for (a) [2 + 2] cycloaddition of 1,2-diphenylmethylenecyclopropene and 1-diethylami...
Scheme 14: Diels–Alder cycloaddition of pentafulvenes derivatives participating as dienes with (i) maleimide d...
Scheme 15: Generic schemes showing pentafulvenes participating as dienophiles in Diels–Alder cycloadditions wi...
Scheme 16: Reaction of 8,8-dicyanoheptafulvene and styrene derivatives to afford [8 + 2] and [4 + 2] cycloaddu...
Scheme 17: Reaction of 6-aminofulvene and maleic anhydride, showing observed [6 + 2] cycloaddition; the [4 + 2...
Scheme 18: Schemes for Diels–Alder cycloadditions in dynamic combinatorial chemistry reported by Boul et al. R...
Scheme 19: Polymerisation and dynamer formation via Diels–Alder cycloaddition between fulvene groups in polyet...
Scheme 20: Preparation of hydrogels via Diels–Alder cycloaddition with fulvene-conjugated dextran and dichloro...
Scheme 21: Ring-opening metathesis polymerisation of norbornene derivatives derived from fulvenes and maleimid...
Analysis of sesquiterpene hydrocarbons in grape berry exocarp (Vitis vinifera L.) using in vivo-labeling and comprehensive two-dimensional gas chromatography–mass spectrometry (GC×GC–MS)
- Philipp P. Könen and
- Matthias Wüst
Beilstein J. Org. Chem. 2019, 15, 1945–1961, doi:10.3762/bjoc.15.190
- consisted of a 30 m × 0.25 mm i.d. × 0.25 µm df DB-WAX Ultra Inert (Agilent Technologies, Bellefonte, PA, U.S.A.) as a high polar primary column with poly(ethylene glycol) as stationary phase coupled to a 1.7 m × 0.10 mm i.d. × 0.10 µm df MEGA-17 MS FAST (MEGA s.n.c., Legnano, MI, IT) moderately polar
Graphical Abstract
Figure 1: Contour plot of a HS-SPME–GC×GC–TOF–MS chromatogram (TIC) demonstrating the separation of volatile ...
Figure 2: Sesquiterpene hydrocarbons found in the headspace of Lemberger (Vitis vinifera subsp. vinifera, clo...
Figure 3: Detailed part of the two-dimensional contour plot (Figure 1) to demonstrate the result of a successful feed...
Scheme 1: First steps towards the formation of sesquiterpenes. The (S)-germacradienyl cation can be formed fr...
Scheme 2: Possible biosynthetic pathways of the sesquiterpene hydrocarbons d8-α-copaene, d8-β-copaene, d8-α-c...
Scheme 3: Mechanistic rationale for the generation of the sesquiterpene hydrocarbons δ-cadinene (14), α-copae...
Figure 4: MS spectra of genuine (d0) and deuterium-labeled (d6 and d8) α-cubebene (left panel) after administ...
Scheme 4: Putative formation pathways of the sesquiterpene hydrocarbons α-ylangene (5), β-ylangene (6), β-bou...
Figure 5: MS spectra and expected labeling patterns of A: d0-α-ylangene, B: d8-α-ylangene after administratio...
Figure 6: Expected labeling patterns of deuterium-labeled, aromatic sesquiterpenes after administration of [6...
Figure 7: MS spectra and expected labeling patterns of genuine and deuterium-labeled A: calamenene (isomer) a...
Figure 8: MS spectra and expected labeling patterns of genuine (d0) and deuterium-labeled (d9) β-elemene afte...
Scheme 5: Possible biosynthesis of d9-β-elemene, d9-(+)-valencene and d9-α-guaiene via germacrene A. *An inco...
Scheme 6: Mechanistic rationale for the generation of the sesquiterpene hydrocarbons γ-elemene and selina-3,7...
Figure 9: Mass spectra and associated structural formulas of d0-γ-elemene and d9-γ-elemene after administrati...
Figure 10: MS spectra and expected labeling patterns of genuine (d0) and deuterium-labeled (d9) guaiazulene af...
Scheme 7: Possible synthesis of d9-guaiazulene, d9-δ-elemene, d9-guaia-6,9-diene and d9-δ-selinene via germac...
Scheme 8: Possible biosynthesis of d6-(E)-β-caryophyllene and d5-α-humulene starting from farnesyl pyrophosph...
Figure 11: MS spectra and expected labeling patterns of d0-(E)-β-caryophyllene and d6-(E)-β-caryophyllene afte...
Synthesis of a [6]rotaxane with singly threaded γ-cyclodextrins as a single stereoisomer
- Jason Yin Hei Man and
- Ho Yu Au-Yeung
Beilstein J. Org. Chem. 2019, 15, 1829–1837, doi:10.3762/bjoc.15.177
- by LC–MS. Contrary to most reports on the inclusion of simple aromatic or poly(ethylene glycol) in γ-CD where a 2:1 binding stoichiometry was observed, LC–MS analysis of the reaction mixture containing a 2:1 molar ratio of 1/γ-CD stoppered by 2 showed only the [3]rotaxane 3R (93%, m/z = 798.0, 4
Graphical Abstract
Scheme 1: Synthesis of the axle and stopper building blocks 1 and 2.
Scheme 2: Synthesis of [n]rotaxanes 3R to 6R. Note that the position and orientation of the γ-CD are arbitrar...
Figure 1: LC–MS analysis of the reaction mixture of the [n]rotaxane synthesis in the presence of (a) 0.5; (b)...
Figure 2: Partial 1H NMR spectra (500 MHz, D2O, 298 K) of (a) 6R; (b) 5R; and (c) 4R.
Figure 3: (a) All the possible sequences of a [6]rotaxane with two CB[6] and three γ-CD interlocked on an axl...
Figure 4: Partial (a) COSY spectrum (500 MHz, D2O, 298 K) and (b) NOESY (500 MHz, D2O, 298 K) of 4R showing t...
Figure 5: Possible structures of 5R assuming no fast shuttling of the γ-CD along the axle.
A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water
- Piyali Sarkar,
- Sayan Sarkar and
- Pradyut Ghosh
Beilstein J. Org. Chem. 2019, 15, 1505–1514, doi:10.3762/bjoc.15.152
- the product was detected when the reaction was carried out in ethanol/water 1:1 (Table 1, entry 12). Even when repeating the reaction in the presence of the phase-transfer catalyst, poly(ethylene glycol) (PEG) no mentionable yield of product was observed (Table 1, entries 13 and 14). The subsequent
Graphical Abstract
Figure 1: Bis-amido-tris-amine macrocycle BATA-MC.
Figure 2: (a) Number distribution plot with particle size in DLS, (b) SEM image and (c) TEM image showing the...
Figure 3: Dependence of the yield of compound 4a on the reaction time using BATA-MC.
Figure 4: Yields of product 4a at different catalyst loading.
Scheme 1: BATA-MC-catalyzed synthesis of 4,5-dihydropyrrolo[2,3,4-kl]acridinones.
Scheme 2: BATA-MC-catalyzed synthesis of pyrrolo[2,3,4-kl]acridinone derivatives.
Figure 5: X-ray single crystal structure of 4d (CCDC 1898008).
Scheme 3: Probable mechanism illustrated for the synthesis of 4a using BATA-MC. For the sake of simplicity, w...
Figure 6: Representation of BATA-MC nanoreactor.
Figure 7: The reusability of the nanoreactor for the synthesis of 4a.
Olefin metathesis in multiblock copolymer synthesis
- Maria L. Gringolts,
- Yulia I. Denisova,
- Eugene Sh. Finkelshtein and
- Yaroslav V. Kudryavtsev
Beilstein J. Org. Chem. 2019, 15, 218–235, doi:10.3762/bjoc.15.21
- -substituted NB with poly(ethylene glycol) (PEG) [69]. Ring-opening metathesis copolymerization of the rather strained cyclooctene (COE) and a strainless 27-membered macrocyclic olefin (MCO) led to the multiblock copolymer consisting of octenylene blocks linked with ring-opened MCO segments (Scheme 6) [70
Graphical Abstract
Scheme 1: Multiblock copolymer synthesis by sequential ROMP, replotted from [51].
Figure 1: The most known commercially available catalysts for olefin metathesis.
Scheme 2: Multiblock copolymer synthesis by combining ROMP and NMP, replotted from [56].
Figure 2: A highly fluorescent multiblock copolymer for bioimaging and in vivo tumor targeting [60].
Scheme 3: Multiblock copolymer synthesis by combining ROMP and click reactions replotted from [61].
Scheme 4: Multiblock copolymer synthesis by combining ADMET and other reactions, replotted from [63,64].
Scheme 5: Synthesis of multiblock bottle-brush copolymers by ROMP, replotted from [68].
Scheme 6: Sacrificial synthesis of multiblock copolymers, replotted from [70].
Scheme 7: Synthesis of supramolecular multiblock copolymers, replotted from [74].
Figure 3: The multiblock copolymer capable of post-functionalization [76].
Figure 4: Multiblock copolymers synthesized by macromolecular cross metathesis.
Scheme 8: Macromolecular cross metathesis.
Figure 5: Changes in the DSC thermograms during MCM of PBD and polyesters (left) [84] and PNB–PCOE (right) mediat...
Figure 6: The 13C NMR spectrum recorded after 8 h of the reaction between PCOE, PNB, and Gr1; the homo- and h...
Scheme 9: Elementary reactions of MCM between PNB and PCOE, replotted from [90].
Figure 7: The 1H NMR spectrum recorded after 24 h of the reaction between PCOE, PNB, and Gr1 in CDCl3. The ca...
Scheme 10: Post-modification of multiblock copolymers by hydrogenation (A) [85] and epoxidation (B) [101] of C=C double...
Figure 8: Integral distribution functions for the lamella thickness of crystallites in thermally fractionated...
Nanoreactors for green catalysis
- M. Teresa De Martino,
- Loai K. E. A. Abdelmohsen,
- Floris P. J. T. Rutjes and
- Jan C. M. van Hest
Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61
- for facile tuning of their properties such as size [13][74], membrane permeability [75] and stability [76]. Various copolymers have been reported for polymersome formation such as poly(ethylene glycol)-b-polystyrene (PEG-b-PS) [14][77], polystyrene-b-polyisocyanopeptide (PS-b-PIAT)[21][22] and poly(N
Graphical Abstract
Figure 1: Assembly of catalyst-functionalized amphiphilic block copolymers into polymer micelles and vesicles...
Scheme 1: C–N bond formation under micellar catalyst conditions, no organic solvent involved. Adapted from re...
Scheme 2: Suzuki−Miyaura couplings with, or without, ppm Pd. Conditions: ArI 0.5 mmol 3a, Ar’B(OH)2 (0.75–1.0...
Figure 2: PQS (4a), PQS attached proline catalyst 4b. Adapted from reference [26]. Copyright 2012 American Chemic...
Figure 3: 3a) Schematic representation of a Pickering emulsion with the enzyme in the water phase (i), or wit...
Scheme 3: Cascade reaction with GOx and Myo. Adapted from reference [82].
Figure 4: Cross-linked polymersomes with Cu(OTf)2 catalyst. Reprinted with permission from [15].
Figure 5: Schematic representation of enzymatic polymerization in polymersomes. (A) CALB in the aqueous compa...
Figure 6: Representation of DSN-G0. Reprinted with permission from [100].
Figure 7: The multivalent esterase dendrimer 5 catalyzes the hydrolysis of 8-acyloxypyrene 1,3,6-trisulfonate...
Figure 8: Conversion of 4-NP in five successive cycles of reduction, catalyzed by Au@citrate, Au@PEG and Au@P...
Solid-state mechanochemical ω-functionalization of poly(ethylene glycol)
- Michael Y. Malca,
- Pierre-Olivier Ferko,
- Tomislav Friščić and
- Audrey Moores
Beilstein J. Org. Chem. 2017, 13, 1963–1968, doi:10.3762/bjoc.13.191
- Michael Y. Malca Pierre-Olivier Ferko Tomislav Friscic Audrey Moores Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC, H3A 0B8, Canada 10.3762/bjoc.13.191 Abstract Poly(ethylene glycol) (PEG) is a linear polymer with a wide range of applications in chemical
- PEG with tosyl, bromide, thiol, carboxylic acid or amine functionalities in good to quantitative yields and with no polymer chain oligomerization, proving the versatility of the method. Keywords: amination; bromination; carboxylation; mechanochemistry; poly(ethylene glycol); solid state; thiolation
- ; tosylation; Introduction Poly(ethylene glycol) (PEG) is a linear polyether polymer with highly hydrophilic properties. Whereas PEG functionalization is restricted to its terminal functionalities, derivatization of these sites is essential for its use in pharmaceutical and material design. Specifically
Graphical Abstract
Scheme 1: Developed syntheses for accessing by mechanochemistry: (a) mPEG–OTs, (b) mPEG–Br, (c) mPEG–SH, (d) ...
Figure 1: 1H NMR of sample mPEG2000–OTs (Table 1, entry 5) in CDCl3 showing mPEG end group shift after tosylation.
An efficient Pd–NHC catalyst system in situ generated from Na2PdCl4 and PEG-functionalized imidazolium salts for Mizoroki–Heck reactions in water
- Nan Sun,
- Meng Chen,
- Liqun Jin,
- Wei Zhao,
- Baoxiang Hu,
- Zhenlu Shen and
- Xinquan Hu
Beilstein J. Org. Chem. 2017, 13, 1735–1744, doi:10.3762/bjoc.13.168
- activity in Mizoroki–Heck reactions with DMF as solvent [66]. With this regards, we herein report the development of a new poly(ethylene glycol, PEG) and pyridine bi-functionalized imidazolium salt L1 (Figure 1), which was employed as a water soluble NHC ligand precursor for an in situ generated Pd–NHC
Graphical Abstract
Figure 1: Structures of imidazolium salts L1–L3.
Scheme 1: The synthetic route for the preparation of imidazolium salts L1–L3.
Figure 2: Kinetic profiles of Mizoroki–Heck reactions in water, Na2PdCl4/L1 (square), L2 (circle), and L3 (tr...
Figure 3: Reusability of the Na2PdCl4/L1 catalytic system for the catalytic Mizoroki–Heck coupling reaction o...
Energy down converting organic fluorophore functionalized mesoporous silica hybrids for monolith-coated light emitting diodes
- Markus Börgardts and
- Thomas J. J. Müller
Beilstein J. Org. Chem. 2017, 13, 768–778, doi:10.3762/bjoc.13.76
- , 9, and 10 were mixed in ethanol in a ratio of 1:6:17 furnishing a perfect white emission with the CIE chromaticity coordinates of x = 0.33 and y = 0.33. This mixture was then mixed with TEOS (tetraethoxysilane), surfactant P123 (poly(ethylene glycol)-poly(propylene glycol)-poly(ethylene glycol/(EtO
Graphical Abstract
Scheme 1: Synthesis of the triethoxysilyl-functionalized dye precursors 8, 9, and 10.
Figure 1: Absorption (a) and emission (b) spectra of perylene 9, benzofurazane 10, and Nile red precursors 8 ...
Figure 2: CIE 1931 color space chromaticity diagram (2° observer) with the CIE chromaticity coordinates of th...
Figure 3: Number of molecules per 100 nm² and quantum yields of 8@MCM in relation to the loading of hybrid ma...
Figure 4: Solid-state fluorescence quantum yields Φf of grafted hybrid materials in relation to the calculate...
Figure 5: CIE 1931 color space chromaticity diagram (2° observer) with the color space accessible by mixing t...
Figure 6: a) Suspensions of the dye-functionalized silica hybrid materials 8@MCM-3, 9@MCM-3, and 10@MCM-6 as ...
Figure 7: a) Excitation and b) emission spectra of the single dye-functionalized hybrid materials 8@MCM-2, 9@...
Figure 8: Emission spectra of blend [8@MCM-2 + 9@MCM-3 + 10@MCM-6]-1 at different excitation wavelengths (2nd...
Figure 9: Coating of the a) conventional diode setup and b) surface-mounted device (SMD) (left: prior to the ...
Figure 10: Pictures of the coated LEDs in compact device set-up (SMD) and conventional diode design (LED).
Figure 11: CIE chromaticity coordinates of the coated LEDs in compact device set-up (SMD) and conventional dio...
Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications
- Stephen Hill and
- M. Carmen Galan
Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67
- glucose, this particular monosaccharide has been extensively used as an ideal carbon source for CD formation, under a range of experimental conditions. The microwave-assisted synthesis of FCDs from a glucose solution in the presence of poly(ethylene glycol)-200 (PEG-200) by Yang et al. is, to the best of
Graphical Abstract
Scheme 1: Microwave-driven reaction of glucose in the presence of PEG-200 to afford blue-emissive CDs.
Scheme 2: Two-step synthesis of TTDDA-coated CDs generated from acid-refluxed glucose.
Scheme 3: Glucose-derived CDs using KH2PO4 as a dehydrating agent to both form and tune CD’s properties.
Scheme 4: Ultrasonic-mediated synthesis of glucose-derived CDs in the presence of ammonia.
Scheme 5: Tryptophan-derived CDs used for the sensing of peroxynitrite in serum-fortified cell media.
Scheme 6: Glucose-derived CDs conjugated with methotrexate for the treatment of H157 lung cancer cells.
Scheme 7: Boron-doped blue-emissive CDs used for sensing of Fe3+ ion in solution.
Scheme 8: N/S-doped CDs with aggregation-induced fluorescence turn-off to temperature and pH stimuli.
Scheme 9: N/P-doped hollow CDs for efficient drug delivery of doxorubicin.
Scheme 10: N/P-doped CDs applied to the sensing of Fe3+ ions in mammalian T24 cells.
Scheme 11: Comparative study of CDs formed from glucose and N-doped with TTDDA and dopamine.
Scheme 12: Formation of blue-emissive CDs from the microwave irradiation of glycerol, TTDDA and phosphate.
Scheme 13: Xylitol-derived N-doped CDs with excellent photostability demonstrating the importance of Cl incorp...
Scheme 14: Base-mediated synthesis of CDs with nanocrystalline cores, from fructose and maltose, without forci...
Scheme 15: N/P-doped green-emissive CDs working in tandem with hyaluronic acid-coated AuNPs to monitor hyaluro...
Scheme 16: Three-minute microwave synthesis of Cl/N-doped CDs from glucosamine hydrochloride and TTDDA to affo...
Scheme 17: Mechanism for the formation of N/Cl-doped CDs via key aldehyde and iminium intermediates, monitored...
Scheme 18: Phosphoric acid-mediated synthesis of orange-red emissive CDs from sucrose.
Scheme 19: Proposed HMF dimer, and its formation mechanism, that upon aggregations bestows orange-red emissive...
Scheme 20: Different polysaccharide-derived CDs in the presence of PEG-200 and how the starting material compo...
Scheme 21: Tetracycline release profiles for differentially-decorated CDs.
Scheme 22: Hyaluronic acid (HA) and glycine-derived CDs, suspected to be decorated in unreacted HA, allowing r...
Scheme 23: Cyclodextrin-derived CDs used for detection of Ag+ ions in solution, based on the formal reduction ...
Scheme 24: Cyclodextrin and OEI-derived CDs, coated with hyaluronic acid and DOX, to produce an effective lung...
Scheme 25: Cellulose and urea-derived N-doped CDs with green-emissive fluorescence.
Synthesis of 1-indanones with a broad range of biological activity
- Marika Turek,
- Dorota Szczęsna,
- Marek Koprowski and
- Piotr Bałczewski
Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48
Graphical Abstract
Figure 1: Biologically active 1-indanones and their structural analogues.
Figure 2: Number of papers about (a) 1-indanones, (b) synthesis of 1-indanones.
Scheme 1: Synthesis of 1-indanone (2) from hydrocinnamic acid (1).
Scheme 2: Synthesis of 1-indanone (2) from 3-(2-bromophenyl)propionic acid (3).
Scheme 3: Synthesis of 1-indanones 5 from 3-arylpropionic acids 4.
Scheme 4: Synthesis of kinamycin (9a) and methylkinamycin C (9b).
Scheme 5: Synthesis of trifluoromethyl-substituted arylpropionic acids 12, 1-indanones 13 and dihydrocoumarin...
Scheme 6: Synthesis of 1-indanones 16 from benzoic acids 15.
Scheme 7: Synthesis of 1-indanones 18 from arylpropionic and 3-arylacrylic acids 17.
Scheme 8: The NbCl5-induced one-step synthesis of 1-indanones 22.
Scheme 9: Synthesis of biologically active 1-indanone derivatives 26.
Scheme 10: Synthesis of enantiomerically pure indatraline ((−)-29).
Scheme 11: Synthesis of 1-indanone (2) from the acyl chloride 30.
Scheme 12: Synthesis of the mechanism-based inhibitors 33 of coelenterazine.
Scheme 13: Synthesis of the indane 2-imidazole derivative 37.
Scheme 14: Synthesis of fluorinated PAHs 41.
Scheme 15: Synthesis of 1-indanones 43 via transition metal complexes-catalyzed carbonylative cyclization of m...
Scheme 16: Synthesis of 6-methyl-1-indanone (46).
Scheme 17: Synthesis of 1-indanone (2) from ester 48.
Scheme 18: Synthesis of benzopyronaphthoquinone 51 from the spiro-1-indanone 50.
Scheme 19: Synthesis of the selective endothelin A receptor antagonist 55.
Scheme 20: Synthesis of 1-indanones 60 from methyl vinyl ketone (57).
Scheme 21: Synthesis of 1-indanones 64 from diethyl phthalate 61.
Scheme 22: Synthesis of 1-indanone derivatives 66 from various Meldrum’s acids 65.
Scheme 23: Synthesis of halo 1-indanones 69.
Scheme 24: Synthesis of substituted 1-indanones 71.
Scheme 25: Synthesis of spiro- and fused 1-indanones 73 and 74.
Scheme 26: Synthesis of spiro-1,3-indanodiones 77.
Scheme 27: Mechanistic pathway for the NHC-catalyzed Stetter–Aldol–Michael reaction.
Scheme 28: Synthesis of 2-benzylidene-1-indanone derivatives 88a–d.
Scheme 29: Synthesis of 1-indanone derivatives 90a–i.
Scheme 30: Synthesis of 1-indanones 96 from o-bromobenzaldehydes 93 and alkynes 94.
Scheme 31: Synthesis of 3-hydroxy-1-indanones 99.
Scheme 32: Photochemical preparation of 1-indanones 103 from ketones 100.
Scheme 33: Synthesis of chiral 3-aryl-1-indanones 107.
Scheme 34: Photochemical isomerization of 2-methylbenzil 108.
Scheme 35: Synthesis of 2-hydroxy-1-indanones 111a–c.
Scheme 36: Synthesis of 1-indanone derivatives 113 and 114 from η6-1,2-dioxobenzocyclobutene complex 112.
Scheme 37: Synthesis of nakiterpiosin (117).
Scheme 38: Synthesis of 2-alkyl-1-indanones 120.
Scheme 39: Synthesis of fluorine-containing 1-indanone derivatives 123.
Scheme 40: Synthesis of 2-benzylidene and 2-benzyl-1-indanones 126, 127 from the chalcone 124.
Scheme 41: Synthesis of 2-bromo-6-methoxy-3-phenyl-1-indanone (130).
Scheme 42: Synthesis of combretastatin A-4-like indanones 132a–s.
Figure 3: Chemical structures of investigated dienones 133 and synthesized cyclic products 134–137.
Figure 4: Chemical structures of 1-indanones and their heteroatom analogues 138–142.
Scheme 43: Synthesis of 2-phosphorylated and 2-non-phosphorylated 1-indanones 147 and 148 from β-ketophosphona...
Scheme 44: Photochemical synthesis of 1-indanone derivatives 150, 153a, 153b.
Scheme 45: Synthesis of polysubstituted-1-indanones 155, 157.
Scheme 46: Synthesis of 1-indanones 159a–g from α-arylpropargyl alcohols 158 using RhCl(PPh3)3 as a catalyst.
Scheme 47: Synthesis of optically active 1-indanones 162 via the asymmetric Rh-catalyzed isomerization of race...
Scheme 48: Mechanism of the Rh-catalyzed isomerization of α-arylpropargyl alcohols 161 to 1-indanones 162.
Figure 5: Chemical structure of abicoviromycin (168) and its new benzo derivative 169.
Scheme 49: Synthesis of racemic benzoabicoviromycin 172.
Scheme 50: Synthesis of [14C]indene 176.
Scheme 51: Synthesis of indanone derivatives 178–180.
Scheme 52: Synthesis of racemic pterosin A 186.
Scheme 53: Synthesis of trans-2,3-disubstituted 1-indanones 189.
Scheme 54: Synthesis of 3-aryl-1-indanone derivatives 192.
Scheme 55: Synthesis of 1-indanone derivatives 194 from 3-(2-iodoaryl)propanonitriles 193.
Scheme 56: Synthesis of 1-indanones 200–204 by cyclization of aromatic nitriles.
Scheme 57: Synthesis of 1,1’-spirobi[indan-3,3’-dione] derivative 208.
Scheme 58: Total synthesis of atipamezole analogues 211.
Scheme 59: Synthesis of 3-[4-(1-piperidinoethoxy)phenyl]spiro[indene-1,1’-indan]-5,5’-diol hydrochloride 216.
Scheme 60: Synthesis of 3-arylindan-1-ones 219.
Scheme 61: Synthesis of 2-hydroxy-1-indanones 222.
Scheme 62: Synthesis of the 1-indanone 224 from the THP/MOM protected chalcone epoxide 223.
Scheme 63: Synthesis of 1-indanones 227 from γ,δ-epoxy ketones 226.
Scheme 64: Synthesis of 2-hydroxy-2-methylindanone (230).
Scheme 65: Synthesis of 1-indanone derivatives 234 from cyclopropanol derivatives 233.
Scheme 66: Synthesis of substituted 1-indanone derivatives 237.
Scheme 67: Synthesis of 7-methyl substituted 1-indanone 241 from 1,3-pentadiene (238) and 2-cyclopentenone (239...
Scheme 68: Synthesis of disubstituted 1-indanone 246 from the siloxydiene 244 and 2-cyclopentenone 239.
Scheme 69: Synthesis of 5-hydroxy-1-indanone (250) via the Diels–Alder reaction of 1,3-diene 248 with sulfoxid...
Scheme 70: Synthesis of halogenated 1-indanones 253a and 253b.
Scheme 71: Synthesis of 1-indanones 257 and 258 from 2-bromocyclopentenones 254.
Scheme 72: Synthesis of 1-indanone 261 from 2-bromo-4-acetoxy-2-cyclopenten-1-one (260) and 1,2-dihydro-4-viny...
Scheme 73: Synthesis of 1-indanone 265 from 1,2-dihydro-7-methoxy-4-vinylnaphthalene (262) and bromo-substitut...
Scheme 74: Synthesis of 1-indanone 268 from dihydro-3-vinylphenanthrene 266 and 4-acetoxy-2-cyclopenten-1-one (...
Scheme 75: Synthesis of 1-indanone 271 from phenylselenyl-substituted cyclopentenone 268.
Scheme 76: Synthesis of 1-indanone 272 from the trienone 270.
Scheme 77: Synthesis of the 1-indanone 276 from the aldehyde 273.
Scheme 78: Synthesis of 1-indanones 278 and 279.
Scheme 79: Synthesis of 1-indanone 285 from octa-1,7-diyne (282) and cyclopentenone 239.
Scheme 80: Synthesis of benz[f]indan-1-one (287) from cyclopentenone 239 and o-bis(dibromomethyl)benzene (286)....
Scheme 81: Synthesis of 3-methyl-substituted benz[f]indan-1-one 291 from o-bis(dibromomethyl)benzene (286) and...
Scheme 82: Synthesis of benz[f]indan-1-one (295) from the anthracene epidioxide 292.
Scheme 83: Synthesis of 1-indanone 299 from homophthalic anhydride 298 and cyclopentynone 297.
Scheme 84: Synthesis of cyano-substituted 1-indanone derivative 301 from 2-cyanomethylbenzaldehyde (300) and c...
Scheme 85: Synthesis of 1-indanone derivatives 303–305 from ketene dithioacetals 302.
Scheme 86: Synthesis of 1-indanones 309–316.
Scheme 87: Mechanism of the hexadehydro-Diels–Alder (HDDA) reaction.
Scheme 88: Synthesis of 1-indenone 318 and 1-indanones 320 and 321 from tetraynes 317 and 319.
Scheme 89: Synthesis of 1-indanone 320 from the triyn 319.
Scheme 90: Synthesis 1-indanone 328 from 2-methylfuran 324.
Scheme 91: Synthesis of 1-indanones 330 and 331 from furans 329.
Scheme 92: Synthesis of 1-indanone 333 from the cycloadduct 332.
Scheme 93: Synthesis of (S)-3-arylindan-1-ones 335.
Scheme 94: Synthesis of (R)-2-acetoxy-1-indanone 338.
Figure 6: Chemical structures of obtained cyclopenta[α]phenanthrenes 339.
Scheme 95: Synthesis of the benzoindanone 343 from arylacetaldehyde 340 with 1-trimethylsilyloxycyclopentene (...
Diels–Alder reactions of myrcene using intensified continuous-flow reactors
- Christian H. Hornung,
- Miguel Á. Álvarez-Diéguez,
- Thomas M. Kohl and
- John Tsanaktsidis
Beilstein J. Org. Chem. 2017, 13, 120–126, doi:10.3762/bjoc.13.15
- myrcene (1, 90% purity), maleic anhydride (2a), acrylic acid (2b), itaconic acid (2c), dimethyl maleate (2d), ethyl acrylate (2f) and poly(ethylene glycol) methyl ether acrylate (PEGA, 2g) were obtained from Sigma-Aldrich; bis(2-ethylhexyl) maleate was provided by TriTech Lubricants. The solvents
Graphical Abstract
Scheme 1: Diels–Alder reaction of myrcene (1), with various dienophiles 2.
Figure 1: Kinetic studies of the Diels–Alder reaction between myrcene (1) and acrylic acid (2b); a) for diffe...
Figure 2: Comparison of conversions in three different reactors for the Diels–Alder reaction of myrcene (1) w...
Poly(ethylene glycol)s as grinding additives in the mechanochemical preparation of highly functionalized 3,5-disubstituted hydantoins
- Andrea Mascitti,
- Massimiliano Lupacchini,
- Ruben Guerra,
- Ilya Taydakov,
- Lucia Tonucci,
- Nicola d’Alessandro,
- Frederic Lamaty,
- Jean Martinez and
- Evelina Colacino
Beilstein J. Org. Chem. 2017, 13, 19–25, doi:10.3762/bjoc.13.3
Graphical Abstract
Scheme 1: PEG-assisted grinding strategy for the preparation of 3,5-disubstituted hydantoins.
