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Search for "drugs" in Full Text gives 723 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks
- Zhang Dongxu
Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127
- more in-depth applications of fluoromethylated hydrazones and acylhydrazones to synthesize natural product analogues and fluorinated drugs is highly desirable. These methods should encourage the introduction of these difluoromethylated nitrogen-containing building blocks in future bioactives discovery
Graphical Abstract
Scheme 1: Synthesis of trifluoromethylpyrazoles from trifluoroacetaldehyde hydrazones.
Scheme 2: Synthesis of polysubstituted pyrazolidines and pyrazolines.
Scheme 3: Asymmetric synthesis of 3-trifluoromethyl-1,4-dihydropyridazines reported by Rueping et al. [39].
Scheme 4: Synthesis of 3-trifluoromethyl-1,4-dihydropyridazine with Brønsted acid-assisted Lewis base catalys...
Scheme 5: Synthesis of CF3-pyrazoles and CF3-1,6-dihydropyridazines.
Scheme 6: Asymmetric reactions of trifluoromethylimines with organometallic reagents.
Scheme 7: Mannich-type reaction of trifluoroacetaldehyde hydrazones.
Scheme 8: Synthesis of trifluoromethylated hydrazonoyl halides.
Scheme 9: Early work of trifluoromethylated hydrazonoyl halides.
Scheme 10: [3 + 2]/[3 + 3] Cycloadditions of trifluoromethylated hydrazonoyl halides.
Scheme 11: Substrate scope for [3 + 2] cycloadditions with trifluoroacetonitrile imines reported by Jasiński’s...
Scheme 12: Synthesis of trifluoromethylated 1,2,4-triazole and 1,2,4-triazine derivatives.
Scheme 13: [3 + 2] Cycloadditions of difluoromethylated hydrazonoyl halides.
Scheme 14: Preparation and early applications of trifluoromethylated acylhydrazones.
Scheme 15: 1,2-Nucleophilic addition reactions of trifluoromethylated acylhydrazones.
Scheme 16: Cascade oxidation/cyclization reactions of trifluoromethylated homoallylic acylhydrazines.
Scheme 17: Synthesis of trifluoromethylated cyanohydrazines and 3-trifluoromethyl-1,2,4-triazolines.
Scheme 18: N-Arylation and N-alkylation of trifluoromethyl acylhydrazones.
Scheme 19: [3 + 2]-Cycladditions of trifluoromethyl acylhydrazones.
Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration
- Ghenwa Nasr,
- Hélène Greige-Gerges,
- Sophie Fourmentin,
- Abdelhamid Elaissari and
- Nathalie Khreich
Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115
- (liposomes and CDs) was shown to combine the advantages of each separate system and to circumvent the drawbacks of liposomes and the problems associated with CDs: for instance, studies reported that the DCL increased the entrapment of hydrophobic drugs in liposomes and enhanced the vesicle stability. The DCL
Graphical Abstract
Figure 1: The chemical structure of the native CDs, their three-dimensional structure, and their dimensions (n...
Figure 2: Structures of β-CD derivatives and their degrees of substitution (DS).
Figure 3: The instantaneous effect of CDs on the various liposome membranes at different CD/DPPC molar ratios...
Figure 4: The permeabilizing effect of CDs on the various liposome membranes at different CD/DPPC molar ratio...
Figure 5: The permeabilizing effect of CDs on the various liposome membranes at different CD/DPPC molar ratio...
Secondary metabolites of Diaporthe cameroonensis, isolated from the Cameroonian medicinal plant Trema guineensis
- Bel Youssouf G. Mountessou,
- Élodie Gisèle M. Anoumedem,
- Blondelle M. Kemkuignou,
- Yasmina Marin-Felix,
- Frank Surup,
- Marc Stadler and
- Simeon F. Kouam
Beilstein J. Org. Chem. 2023, 19, 1555–1561, doi:10.3762/bjoc.19.112
- Bel Youssouf G. Mountessou Elodie Gisele M. Anoumedem Blondelle M. Kemkuignou Yasmina Marin-Felix Frank Surup Marc Stadler Simeon F. Kouam Department of Chemistry, Higher Teacher Training College, University of Yaoundé I, P.O. Box 47, Yaoundé, Cameroon Department of Microbial Drugs, Helmholtz
Graphical Abstract
Figure 1: Chemical structures of compounds 1 and 2.
Figure 2: Key COSY and HMBC correlations of compounds 1 and 2.
N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations
- Fatemeh Doraghi,
- Seyedeh Pegah Aledavoud,
- Mehdi Ghanbarlou,
- Bagher Larijani and
- Mohammad Mahdavi
Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106
- , peptides, drugs and saccharides reacted smoothly with N-alkynylthiophthalimides in the presence of TFA as a catalyst. Also, aliphatic and aromatic thiols reacted with N-alkynylthiophthalimide and sulfoxide 149 to obtain acyl disulfides 151 through alkynylthiolation and hydrative oxyarylation in the
Graphical Abstract
Scheme 1: Sulfur-containing bioactive molecules.
Scheme 2: Scandium-catalyzed synthesis of thiosulfonates.
Scheme 3: Palladium-catalyzed aryl(alkyl)thiolation of unactivated arenes.
Scheme 4: Catalytic cycle for Pd-catalyzed aryl(alkyl)thiolation of unactivated arenes.
Scheme 5: Iron- or boron-catalyzed C–H arylthiation of substituted phenols.
Scheme 6: Iron-catalyzed azidoalkylthiation of alkenes.
Scheme 7: Plausible mechanism for iron-catalyzed azidoalkylthiation of alkenes.
Scheme 8: BF3·Et2O‑mediated electrophilic cyclization of aryl alkynoates.
Scheme 9: Tentative mechanism for BF3·Et2O‑mediated electrophilic cyclization of aryl alkynoates.
Scheme 10: Construction of 6-substituted benzo[b]thiophenes.
Scheme 11: Plausible mechanism for construction of 6-substituted benzo[b]thiophenes.
Scheme 12: AlCl3‑catalyzed cyclization of N‑arylpropynamides with N‑sulfanylsuccinimides.
Scheme 13: Synthetic utility of AlCl3‑catalyzed cyclization of N‑arylpropynamides with N‑sulfanylsuccinimides.
Scheme 14: Sulfenoamination of alkenes with sulfonamides and N-sulfanylsuccinimides.
Scheme 15: Lewis acid/Brønsted acid controlled Pd-catalyzed functionalization of aryl C(sp2)–H bonds.
Scheme 16: Possible mechanism for Lewis acid/Brønsted acid controlled Pd-catalyzed functionalization of aryl C...
Scheme 17: FeCl3-catalyzed carbosulfenylation of unactivated alkenes.
Scheme 18: Copper-catalyzed electrophilic thiolation of organozinc halides.
Scheme 19: h-BN@Copper(II) nanomaterial catalyzed cross-coupling reaction of sulfoximines and N‑(arylthio)succ...
Scheme 20: AlCl3‑mediated cyclization and sulfenylation of 2‑alkyn-1-one O‑methyloximes.
Scheme 21: Lewis acid-promoted 2-substituted cyclopropane 1,1-dicarboxylates with sulfonamides and N-(arylthio...
Scheme 22: Lewis acid-mediated cyclization of β,γ-unsaturated oximes and hydrazones with N-(arylthio/seleno)su...
Scheme 23: Credible pathway for Lewis acid-mediated cyclization of β,γ-unsaturated oximes with N-(arylthio)suc...
Scheme 24: Synthesis of 4-chalcogenyl pyrazoles via chalcogenation/cyclization of α,β-alkynic hydrazones.
Scheme 25: Controllable synthesis of 3-thiolated pyrroles and pyrrolines.
Scheme 26: Possible mechanism for controllable synthesis of 3-thiolated pyrroles and pyrrolines.
Scheme 27: Co-catalyzed C2-sulfenylation and C2,C3-disulfenylation of indole derivatives.
Scheme 28: Plausible catalytic cycle for Co-catalyzed C2-sulfenylation and C2,C3-disulfenylation of indoles.
Scheme 29: C–H thioarylation of electron-rich arenes by iron(III) triflimide catalysis.
Scheme 30: Difunctionalization of alkynyl bromides with thiosulfonates and N-arylthio succinimides.·
Scheme 31: Suggested mechanism for difunctionalization of alkynyl bromides with thiosulfonates and N-arylthio ...
Scheme 32: Synthesis of thioesters, acyl disulfides, ketones, and amides by N-thiohydroxy succinimide esters.
Scheme 33: Proposed mechanism for metal-catalyzed selective acylation and acylthiolation.
Scheme 34: AlCl3-catalyzed synthesis of 3,4-bisthiolated pyrroles.
Scheme 35: α-Sulfenylation of aldehydes and ketones.
Scheme 36: Acid-catalyzed sulfetherification of unsaturated alcohols.
Scheme 37: Enantioselective sulfenylation of β-keto phosphonates.
Scheme 38: Organocatalyzed sulfenylation of 3‑substituted oxindoles.
Scheme 39: Sulfenylation and chlorination of β-ketoesters.
Scheme 40: Intramolecular sulfenoamination of olefins.
Scheme 41: Plausible mechanism for intramolecular sulfenoamination of olefins.
Scheme 42: α-Sulfenylation of 5H-oxazol-4-ones.
Scheme 43: Metal-free C–H sulfenylation of electron-rich arenes.
Scheme 44: TFA-promoted C–H sulfenylation indoles.
Scheme 45: Proposed mechanism for TFA-promoted C–H sulfenylation indoles.
Scheme 46: Organocatalyzed sulfenylation and selenenylation of 3-pyrrolyloxindoles.
Scheme 47: Organocatalyzed sulfenylation of S-based nucleophiles.
Scheme 48: Conjugate Lewis base Brønsted acid-catalyzed sulfenylation of N-heterocycles.
Scheme 49: Mechanism for activation of N-sulfanylsuccinimide by conjugate Lewis base Brønsted acid catalyst.
Scheme 50: Sulfenylation of deconjugated butyrolactams.
Scheme 51: Intramolecular sulfenofunctionalization of alkenes with phenols.
Scheme 52: Organocatalytic 1,3-difunctionalizations of Morita–Baylis–Hillman carbonates.
Scheme 53: Organocatalytic sulfenylation of β‑naphthols.
Scheme 54: Acid-promoted oxychalcogenation of o‑vinylanilides with N‑(arylthio/arylseleno)succinimides.
Scheme 55: Lewis base/Brønsted acid dual-catalytic C–H sulfenylation of aryls.
Scheme 56: Lewis base-catalyzed sulfenoamidation of alkenes.
Scheme 57: Cyclization of allylic amide using a Brønsted acid and tetrabutylammonium chloride.
Scheme 58: Catalytic electrophilic thiocarbocyclization of allenes with N-thiosuccinimides.
Scheme 59: Suggested mechanism for electrophilic thiocarbocyclization of allenes with N-thiosuccinimides.
Scheme 60: Chiral chalcogenide-catalyzed enantioselective hydrothiolation of alkenes.
Scheme 61: Proposed mechanism for chalcogenide-catalyzed enantioselective hydrothiolation of alkenes.
Scheme 62: Organocatalytic sulfenylation for synthesis a diheteroatom-bearing tetrasubstituted carbon centre.
Scheme 63: Thiolative cyclization of yne-ynamides.
Scheme 64: Synthesis of alkynyl and acyl disulfides from reaction of thiols with N-alkynylthio phthalimides.
Scheme 65: Oxysulfenylation of alkenes with 1-(arylthio)pyrrolidine-2,5-diones and alcohols.
Scheme 66: Arylthiolation of arylamines with (arylthio)-pyrrolidine-2,5-diones.
Scheme 67: Catalyst-free isothiocyanatoalkylthiation of styrenes.
Scheme 68: Sulfenylation of (E)-β-chlorovinyl ketones toward 3,4-dimercaptofurans.
Scheme 69: HCl-promoted intermolecular 1, 2-thiofunctionalization of aromatic alkenes.
Scheme 70: Possible mechanism for HCl-promoted 1,2-thiofunctionalization of aromatic alkenes.
Scheme 71: Coupling reaction of diazo compounds with N-sulfenylsuccinimides.
Scheme 72: Multicomponent reactions of disulfides with isocyanides and other nucleophiles.
Scheme 73: α-Sulfenylation and β-sulfenylation of α,β-unsaturated carbonyl compounds.
Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence
- Nadia Ledermann,
- Alae-Eddine Moubsit and
- Thomas J. J. Müller
Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99
- state, in good yield. Keywords: alkynylation; catalysis; cyclization; indoles; iodination; multicomponent reactions; Introduction Indoles and their derived substitution patterns are omnipresent heterocyclic structural motifs in nature [1], many natural products [2][3], drugs [4][5][6][7][8], and dyes
Graphical Abstract
Scheme 1: Consecutive alkynylation–cyclization–alkylation three-component synthesis and conception of a conse...
Scheme 2: Consecutive alkynylation–cyclization–iodination–alkylation four-component synthesis of trisubstitut...
Scheme 3: Consecutive double alkynylation–cyclization–iodination–alkylation pseudo-five-component synthesis o...
Scheme 4: Suzuki coupling of 3-iodoindole 5a with arylboronic acids 7 to give 1,2,3-trisubstituted indoles 8.
Figure 1: A: Absorption and emission spectra of 1-methyl-2-phenyl-3-(p-tolyl)-1H-indole (8b), recorded in dic...
Synthesis of ether lipids: natural compounds and analogues
- Marco Antônio G. B. Gomes,
- Alicia Bauduin,
- Chloé Le Roux,
- Romain Fouinneteau,
- Wilfried Berthe,
- Mathieu Berchel,
- Hélène Couthon and
- Paul-Alain Jaffrès
Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96
Graphical Abstract
Figure 1: Chemical structure of some natural ether lipids (ELs).
Figure 2: Synthesis of lyso-PAF and PAF from 1-O-alkylglycerol [64].
Figure 3: Synthesis of lyso-PAF from 1,3-benzylideneglycerol 3.1 [69].
Figure 4: A) Synthesis of the two enantiomers of octadecylglycerol (4.6 and 4.10) from ᴅ-mannitol (4.1); B) s...
Figure 5: Four-step synthesis of PAF 5.6 from (S)-glycidol [73].
Figure 6: Synthesis of 1-O-alkylglycerol A) from solketal, B) from ᴅ- or ʟ-tartaric acid and the intermediate ...
Figure 7: Synthesis of EL building blocks starting from substituted glycidol 7.1a–c [82].
Figure 8: Synthesis of PAF 8.5 by using phosphoramidite 8.2 [86].
Figure 9: Synthesis of oleyl-PAF 9.7 from ʟ-serine [88].
Figure 10: Synthesis of racemic analogues of lyso-PAF 10.8 and PAF 10.9 featuring a phenyl group between the g...
Figure 11: Synthesis of racemic deoxy-lyso-PAF 11.7 and deoxy-PAF 11.8 [91].
Figure 12: Synthesis of racemic thio-PAF 12.8 [93].
Figure 13: Racemic synthesis of 13.6 to illustrate the modification of the glycerol backbone by adding a methy...
Figure 14: Racemic synthesis of 14.5 as an illustration of the introduction of methyl substituents on the glyc...
Figure 15: Synthesis of functionalized sn-2-acyl chains of PC-EL; A) Steglich esterification or acylation reac...
Figure 16: Synthesis of racemic mc-PAF (16.3), a carbamate analogue of PAF [102].
Figure 17: A) Synthesis of (R)-17.2 and (S)-17.6 starting from (S)-solketal (17.1); B) synthesis of N3-PAF (17...
Figure 18: Modification of the phosphocholine polar head to produce PAF analogues [81].
Figure 19: Racemic PAF analogues 19.3 and 19.5 characterized by the absence of the phosphate group [107].
Figure 20: Synthesis of PIP3-PAF (20.7) [108].
Figure 21: Large-scale synthesis of C18-edelfosine (21.8) [116].
Figure 22: Synthesis of C16-edelfosine (22.10) starting from isopropylidene-ʟ-glyceric acid methyl ester (22.1...
Figure 23: Phosphocholine moiety installation by the use of chlorophosphite 23.2 as key reagent [119].
Figure 24: Synthesis of rac-1-alkyl-2-O-methylglycerol (AMG) [120].
Figure 25: Synthesis of stereocontrolled 1-alkyl-2-O-methyl glycerol 25.9 (AMG) from dimethyl ᴅ-tartrate [81].
Figure 26: A) Racemic synthesis of thioether 26.4 [129,130], B) structure of sulfone analogue 26.5 [129].
Figure 27: Stereocontrolled synthesis of C18-edelfosine thioether analogue 27.8 [118].
Figure 28: Synthesis of thioether 28.4 that include a thiophosphate function [134].
Figure 29: Synthesis of ammonium thioether 29.4 and 29.6 [135].
Figure 30: Synthesis of the N-methylamino analogue of edelfosine 30.6 (BN52211) [138].
Figure 31: Synthesis of 1-desoxy analogues of edelfosine; A) with a saturated alkyl chain; B) synthesis of the...
Figure 32: Stereocontrolled synthesis of edelfosine analogue (S)-32.8 featuring a C18:1 lipid chain [142].
Figure 33: Synthesis of edelfosine analogues with modulation of the lipid chain; A) illustration with the synt...
Figure 34: Synthesis of phospholipid featuring a carbamate function to link the lipid chain to the glycerol un...
Figure 35: Synthesis of sesquiterpene conjugates of phospho glycero ether lipids [148].
Figure 36: Racemic synthesis of methyl-substituted glycerol analogues 36.7 and 36.10: A) synthesis of diether ...
Figure 37: Racemic synthesis of ilmofosine (37.6) [155,156].
Figure 38: A) Stereoselective synthesis of 38.5 via a stereoselective hydroboration reaction; B) synthesis of ...
Figure 39: Racemic synthesis of SRI62-834 (39.6) featuring a spiro-tetrahydrofurane heterocycle in position 2 ...
Figure 40: Racemic synthesis of edelfosine analogue 40.5 featuring an imidazole moiety in sn-2 position [160].
Figure 41: Racemic synthesis of fluorine-functionalized EL: A) Synthesis of 41.6 and B) synthesis of 41.8 [161-163].
Figure 42: A) Synthesis of the β-keto-ester 42.6 that also features a decyl linker between the phosphate and t...
Figure 43: Synthesis of phosphonate-based ether lipids; A) edelfosine phosphonate analogue 43.7 and B) thioeth...
Figure 44: Enantioselective synthesis of phosphonates 44.3 and 44.4 [171].
Figure 45: Racemic synthesis of phosphinate-based ether lipid 45.10 [172].
Figure 46: Racemic synthesis of edelfosine arsonium analogue 46.5 [173].
Figure 47: Synthesis of edelfosine dimethylammonium analogue 47.2 [118].
Figure 48: Synthesis of rac-C18-edelfosine methylammonium analogue 48.4 [176].
Figure 49: A) Synthesis of edelfosine N-methylpyrrolidinium analogue 49.2 or N-methylmorpholinium analogue 49.3...
Figure 50: A) Synthesis of edelfosine’s analogue 50.4 with a PE polar group; B) illustration of a pyridinium d...
Figure 51: A) Synthesis of 51.4 featuring a thiazolium cationic moiety; B) synthesis of thiazolium-based EL 51...
Figure 52: Synthesis of cationic ether lipids 52.3, 52.4 and 52.6 [135,183].
Figure 53: Synthesis of cationic carbamate ether lipid 53.5 [184].
Figure 54: Synthesis of cationic sulfonamide 54.5 [185].
Figure 55: Chemical structure of ONO-6240 (55.1) and SRI-63-119 (55.2).
Figure 56: Synthesis of non-ionic ether lipids 56.2–56.9 [188].
Figure 57: Synthesis of ether lipid conjugated to foscarnet 57.6 [189].
Figure 58: A) Synthesis of ether lipid conjugated to arabinofuranosylcytosine; B) synthesis of AZT conjugated ...
Figure 59: Synthesis of quercetin conjugate to edelfosine [191].
Figure 60: Synthesis of 60.8 (Glc-PAF) [194].
Figure 61: A) Synthesis of amino ether lipid 61.7 functionalized with a rhamnose unit and its amide analogue 6...
Figure 62: A) Synthesis of glucose ether lipid 62.4; B) structure of ether lipid 62.5 possessing a maltose uni...
Figure 63: A) Synthesis of glucuronic methyl ester 63.8; B) structure of cellobiose 63.9 and maltose 63.10 ana...
Figure 64: A) Synthesis of maltosyl glycerolipid 64.7; B) structure of lactose analogue 64.8 prepared followin...
Figure 65: A) Asymmetric synthesis of the aglycone moiety starting from allyl 4-methoxyphenyl ether; B) glycos...
Figure 66: A) Synthesis of ohmline possessing a lactose moiety. B) Structure of other glyco glycero lipids pre...
Figure 67: A) Synthesis of lactose-glycerol ether lipid 67.5; B) analogues possessing a maltose (67.6) or meli...
Figure 68: Synthesis of digalactosyl EL 68.6, A) by using trityl, benzyl and acetyl protecting groups, B) by u...
Figure 69: A) Synthesis of α-ohmline; B) structure of disaccharide ether lipids prepared by using similar meth...
Figure 70: Synthesis of lactose ether lipid 70.3 and its analogue 70.6 featuring a carbamate function as linke...
Figure 71: Synthesis of rhamnopyranoside diether 71.4 [196].
Figure 72: Synthesis of 1-O-hexadecyl-2-O-methyl-3-S-(α-ᴅ-1'-thioglucopyranosyl)-sn-glycerol (72.5) [225].
Figure 73: A) Preparation of lipid intermediate 73.4; B) synthesis of 2-desoxy-C-glycoside 73.10 [226].
Figure 74: Synthesis of galactose-pyridinium salt 74.3 [228].
Figure 75: Synthesis of myo-inositol derivative Ino-C2-PAF (75.10) [230].
Figure 76: A) Synthesis of myo-inositol phosphate building block 76.7; B) synthesis of myo-inositolphosphate d...
Figure 77: A) Synthesis of phosphatidyl-3-desoxy-inositol 77.4; B) synthesis of phosphono-3-desoxyinositol 77.9...
Figure 78: A) Structure of diether phosphatidyl-myo-inositol-3,4-diphosphate 78.1; B) synthesis of phosphatidy...
Figure 79: A) Synthesis of diether-phosphatidyl derivative 79.4 featuring a hydroxymethyl group in place of a ...
Figure 80: Synthesis of Glc-amine-PAF [78].
Figure 81: Synthesis of glucosamine ether lipid 81.4 and its analogues functionalized in position 3 of the ami...
Figure 82: Synthesis of fully deprotected aminoglucoside ether lipid 82.5 [246].
Figure 83: Synthesis of C-aminoglycoside 83.12 using Ramberg–Bäcklund rearrangement as a key step [250].
Figure 84: A) List of the most important glyco lipids and amino glyco lipids included in the study of Arthur a...
Figure 85: Synthesis of mannosamine ether lipid 85.6 [254].
Figure 86: A) Synthesis of glucosamine ether lipids with a non-natural ʟ-glucosamine moiety; B) synthesis of e...
Figure 87: A) Structure of the most efficient anticancer agents 87.1–87.4 featuring a diamino glyco ether lipi...
Figure 88: A) Synthesis of diamino glyco ether lipid 87.4; B) synthesis of bis-glycosylated ether lipid 88.10 [256]....
Figure 89: Synthesis of triamino ether lipid 89.4 [260].
Figure 90: Synthesis of chlorambucil conjugate 90.7 [261].
Figure 91: Three main methods for the preparation of glycerol ether lipid 91.3; A) from solketal and via a tri...
Figure 92: Four different methods for the installation of the phosphocholine polar head group; A) method using...
Figure 93: Illustration of two methods for the installation of saccharides or aminosaccharides; A) O-glycosyla...
Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp3)–H to construct C–C bonds
- Hui Yu and
- Feng Xu
Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94
- are widespread as essential building blocks in various drugs, natural products, agrochemicals, and materials. Modern economy requires developing green strategies with improved efficiency and reduction of waste. Due to its atom and step-economy, the cross-dehydrogenative coupling (CDC) reaction has
- CDC reaction to be a new generation method for the construction of C–C bonds and it has received extensive attention and in-depth research [16][17][18][19][20][21][22][23][24]. The building blocks of ethers are widely found in biomass, chemical feedstocks, biologically active drugs, and natural
- drugs are shown in Scheme 1c: Empagliflozin to treat type-2 diabetes [34][35][36], tegafur is used in medicine to treat a variety of cancers [37][38], lubazodone is an experimental antidepressant [39][40], and sofosbuvir is used to treat hepatitis C virus (HCV) infections [41][42]. For the synthesis of
Graphical Abstract
Scheme 1: Research progress of coupling reactions and active compounds containing α-C(sp3)-functionalized eth...
Scheme 2: Transition-metal-catalyzed CDC pathways.
Scheme 3: CDC of active methylene compounds in the α-C(sp3) position of ethers.
Scheme 4: InCl3/Cu(OTf)2/NHPI co-catalyzed CDC reaction.
Scheme 5: CDC of cyclic benzyl ethers with aldehydes.
Scheme 6: Cu-catalyzed CDC of (a) unactivated C(sp3)–H ethers with simple ketones and (b) double C(sp3)−H fun...
Scheme 7: Cu-catalyzed CDC of C(sp3)–H/C(sp3)–H bonds.
Scheme 8: Cu-catalyzed synthesis of chiral 2-substituted tetrahydropyrans.
Scheme 9: CDC of thiazole with cyclic ethers.
Scheme 10: Cu(I)-catalyzed oxidative alkenylation of simple ethers.
Scheme 11: Cross-dehydrogenation coupling of isochroman C(sp3)–H bonds with anisole C(sp2)–H bonds.
Scheme 12: Pd(OAc)2/Cu(OTf)2-catalyzed arylation of α-C(sp3)–H bonds of ethers.
Scheme 13: Cu-catalyzed C(sp3)–H/C(sp2)–H activation strategies to construct C(sp3)–C(sp2) bonds.
Scheme 14: Cu(I)-catalyzed C(sp2)–H alkylation.
Scheme 15: Cu-catalyzed C(sp3)–H/C(sp)–H activation to construct C(sp3)–C(sp) bonds (H2BIP: 2,6-bis(benzimidaz...
Scheme 16: Fe-catalyzed CDC reaction pathways.
Scheme 17: Fe2(CO)9-catalyzed functionalization of C–H bonds.
Scheme 18: Ligand-promoted Fe-catalyzed CDC reaction of N-methylaniline with ethers.
Scheme 19: Fe-catalyzed CDC of C(sp3)–H/C(sp3)–H bonds.
Scheme 20: Fe-catalyzed hydroalkylation of α,β-unsaturated ketones with ethers.
Scheme 21: Solvent-free Fe(NO3)3-catalyzed CDC of C(sp3)–H/C(sp2)–H bonds.
Scheme 22: Alkylation of disulfide compounds to afford tetrasubstituted alkenes.
Scheme 23: Fe-catalyzed formation of 1,1-bis-indolylmethane derivatives.
Scheme 24: Alkylation of coumarins and flavonoids.
Scheme 25: Direct CDC α-arylation of azoles with ethers.
Scheme 26: CDC of terminal alkynes with C(sp3)–H bonds adjacent to oxygen, sulfur or nitrogen atoms.
Scheme 27: Alkylation of terminal alkynes.
Scheme 28: Co-catalyzed functionalization of glycine esters.
Scheme 29: Co-catalyzed construction of C(sp2)–C(sp3) bonds.
Scheme 30: Co-catalyzed CDC of imidazo[1,2-a]pyridines with isochroman.
Scheme 31: Co-catalyzed C–H alkylation of (benz)oxazoles with ethers.
Scheme 32: Cobalt-catalyzed CDC between unactivated C(sp2)–H and C(sp3)–H bonds.
Scheme 33: MnO2-catalyzed CDC of the inactive C(sp3)-H.
Scheme 34: Oxidative cross-coupling of ethers with enamides.
Scheme 35: Ni(II)-catalyzed CDC of indoles with 1,4-dioxane.
Scheme 36: Chemo- and regioselective ortho- or para-alkylation of pyridines.
Scheme 37: Asymmetric CDC of 3,6-dihydro-2H-pyrans with aldehydes.
Scheme 38: CDC of heterocyclic aromatics with ethers.
Scheme 39: Indium-catalyzed alkylation of DHPs with 1,3-dicarbonyl compounds.
Scheme 40: Rare earth-metal-catalyzed CDC reaction.
Scheme 41: Visible-light-driven CDC of cycloalkanes with benzazoles.
Scheme 42: Photoinduced alkylation of quinoline with cyclic ethers.
Scheme 43: Photocatalyzed CDC reactions between α-C(sp3)–H bonds of ethers and C(sp2)–H bonds of aromatics.
Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita–Baylis–Hillman (MBH) alcohols and acetates
- Olfa Mhasni,
- Jalloul Bouajila and
- Farhat Rezgui
Beilstein J. Org. Chem. 2023, 19, 1251–1258, doi:10.3762/bjoc.19.93
- bifonazole have become well-established drugs for the treatment of numerous mycotic infections (Figure 1) [9][10]. Therefore, the development of new methods for the preparation of such compounds is highly required. The MBH acetates, instead of the corresponding alcohols, have been extensively used as
Graphical Abstract
Figure 1: Medicines containing an imidazole nucleus.
Scheme 1: Synthesis of N-substituted imidazole derivatives from MBH adducts.
Scheme 2: Proposed mechanism for the allylation of imidazole with alcohol 4a.
Radical ligand transfer: a general strategy for radical functionalization
- David T. Nemoto Jr,
- Kang-Jie Bian,
- Shih-Chieh Kao and
- Julian G. West
Beilstein J. Org. Chem. 2023, 19, 1225–1233, doi:10.3762/bjoc.19.90
- intermediate. RLT to this radical from another azide ligand leads to a diazidated product. The overall scope of both reports suggests that the diazidation of simple to complex drugs/natural product-derived alkene substrates is readily achievable, including highly substituted and cyclic aliphatic alkenes
Graphical Abstract
Scheme 1: Overview of the RLT mechanism in nature and in literature. I: The radical rebound mechanism in cyto...
Scheme 2: Areas of recent work on RLT development and application in catalysis. I: Reported RLT pathways ofte...
Scheme 3: The incorporation of RLT catalysis in ATRA photocatalysis. I: The reported method is compatible wit...
Scheme 4: Pioneering and recent work on decarboxylative functionalization involving a posited RLT pathway. I:...
Scheme 5: Our lab reported decarboxylative azidation of aliphatic and benzylic acids. I: The reaction proceed...
Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives
- Valeriy O. Filimonov,
- Alexandra I. Topchiy,
- Vladimir G. Ilkin,
- Tetyana V. Beryozkina and
- Vasiliy A. Bakulev
Beilstein J. Org. Chem. 2023, 19, 1191–1197, doi:10.3762/bjoc.19.87
- mercaptopurine (Figure 1), containing an intracyclic thioamide group, are antagonists of purine bases and are well known as cytostatic drugs [13]. The thioamide group as an amide isostere is used in medical chemistry to increase thermal and proteolytic stability and improve the pharmacokinetic properties of
- : deposit@ccdc.cam.ac.uk). Examples of bioactive pyrazoles for the protection of cultivated plants and drugs containing a thiocarbonyl group. Structures of starting materials. Syntheses of 4,5-diamino- and 4-thiocarbamoyl-5-aminopyrazoles. Synthesis of 3,5-diaminopyrazoles 4а–с and thiocarbamoyl-NH
Graphical Abstract
Figure 1: Examples of bioactive pyrazoles for the protection of cultivated plants and drugs containing a thio...
Scheme 1: Syntheses of 4,5-diamino- and 4-thiocarbamoyl-5-aminopyrazoles.
Figure 2: Structures of starting materials.
Scheme 2: Synthesis of 3,5-diaminopyrazoles 4а–с and thiocarbamoyl-NH-pyrazoles 5a–e. Reaction conditions: 1a–...
Scheme 3: Synthesis of 1-aryl-5-amino-4-thiocarbamoylpyrazoles 6a–f. Reaction conditions: 2a–d (1 mmol), 3b,c...
Scheme 4: Synthesis of 1-sulfonylpyrazoles 7a–j and 1-benzoylpyrazole 7k. Conditions for 7a–j: 2b,d,e (1 mmol...
Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea
- Winnie Chemutai Sum,
- Sherif S. Ebada,
- Didsanutda Gonkhom,
- Cony Decock,
- Rémy Bertrand Teponno,
- Josphat Clement Matasyoh and
- Marc Stadler
Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84
- Winnie Chemutai Sum Sherif S. Ebada Didsanutda Gonkhom Cony Decock Remy Bertrand Teponno Josphat Clement Matasyoh Marc Stadler Department of Microbial Drugs, Helmholtz Centre for Infection Research GmbH (HZI), Inhoffenstraße 7, 38124 Braunschweig, Germany Institute of Microbiology, Technische
Graphical Abstract
Figure 1: Chemical structures of compounds 1–4.
Figure 2: Key 1H,1H COSY, HMBC, and ROESY correlations of compounds 1 and 2.
Photoredox catalysis harvesting multiple photon or electrochemical energies
- Mattia Lepori,
- Simon Schmid and
- Joshua P. Barham
Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81
Graphical Abstract
Figure 1: Oxidative and reductive activations of organic compounds harvesting photoredox catalysis.
Figure 2: General catalytic cycles of radical ion conPET (left) and radical ion e-PRC (right).
Figure 3: “Beginner’s guide”: comparison between advantages, capacities, and prospectives of conPET and PEC.
Figure 4: A) conPET reductive dehalogenation of aryl halides with PDI. B) Reductive C–H arylation with pyrrol...
Figure 5: A) Chromoselective mono- and disubstitution or polybrominated pyrimidines with pyrroles. B) Sequent...
Figure 6: A) Synthesis of pyrrolo[1,2-a]quinolines. B) Synthesis of ullazines.
Figure 7: A) Reductive phosphorylation of aryl halides via conPET. B) Selected examples from the substrate sc...
Figure 8: A) Reductive dehalogenation of aryl halides via conPET and selected examples from the substrate sco...
Figure 9: A) Reductive C–H arylation of aryl halides via conPET (top) and selected examples from the substrat...
Figure 10: A) Reductive hydrodehalogenation of aryl halides with Mes-Acr-BF4. B) Selected examples from the su...
Figure 11: A) Reductive hydrodechlorination of aryl chlorides with 4-DPAIPN. B) Proposed formation of CO2•−. C...
Figure 12: A) Reductive conPET borylation with 3CzEPAIPN (top) and selected examples from the substrate scope ...
Figure 13: Scale-up of conPET phosphorylation with 3CzEPAIPN.
Figure 14: A) Borylation of 1d. B) Characteristics and structure of PC1 with green and red parts showing the l...
Figure 15: A) Reductive C–H arylation scope with polysulfide conPET (top) and selected examples from the subst...
Figure 16: Scale-up of A) C–H arylation and B) dehaloborylation with polysulfide photocatalysis in continuous-...
Figure 17: A) Formation of [Ir1]0 and [Ir2]0 upon PET between [Ir1]+ and Et3N. B) Mechanism of multi-photon ta...
Figure 18: A) Reductive hydrodehalogenation of aryl halides via multi-photon tandem photocatalysis. B) Selecte...
Figure 19: A) Carbonylative amidation of aryl halides in continuous flow. B) Selected examples from the substr...
Figure 20: A) General scheme for reductive (RQ) and oxidative quenching (OQ) protocols using [FeIII(btz)3](PF6)...
Figure 21: A) Carbonylative amidation of alkyl iodides with [IrIII(ppy)2(dtbbpy)]PF6. B) Selected examples fro...
Figure 22: A) Carboxylative C–N bond cleavage in cyclic amines. B) Selected examples from the substrate scope....
Figure 23: A) Formal reduction of alkenes to alkanes via transfer hydrogenation. B) Selected examples from the...
Figure 24: A) Birch-type reduction of benzenes with PMP-BPI. B) Selected examples from the substrate scope (sc...
Figure 25: Proposed mechanism of the OH− mediated conPET Birch-type reduction of benzene via generation of sol...
Figure 26: Reductive detosylation of N-tosylated amides with Mes-Acr-BF4. B) Selected examples from the substr...
Figure 27: A) Reductive detosylation of N-tosyl amides by dual PRC. B) Selected examples from the substrate sc...
Figure 28: A) Mechanism of the dual PRC based on PET between [Cu(dap)2]+ and DCA. B) Mechanism of the dual PRC...
Figure 29: A) N–O bond cleavage in Weinreb amides with anthracene. B) N–O bond cleavage in Weinreb amides rely...
Figure 30: A) Pentafluorosulfanylation and fluoride elimination. B) Mechanism of the pentafluorosulfanylation ...
Figure 31: A) α-Alkoxypentafluorosulfanylation (top) and selected examples from the substrate scope (bottom). ...
Figure 32: A) Oxidative amination of arenes with azoles catalyzed by N-Ph PTZ. B) Selected examples from the s...
Figure 33: A) C(sp3)–H bond activation by HAT via chloride oxidation by *N-Ph PTZ•+. B) Proposed mechanism for...
Figure 34: A) Recycling e-PRC C–H azolation of electron-rich arenes with pyrazoles using Mes-Acr+ as a photoca...
Figure 35: A) Radical ion e-PRC direct oxidation of unactivated arenes using TAC+ as an electro-activated phot...
Figure 36: A) Radical ion e-PRC direct oxidation of unactivated arenes using TPA as an electro-activated photo...
Figure 37: Proposed mechanism (top) and mode of preassembly (bottom).
Figure 38: A) Possible preassemblies of reactive (left) vs unreactive (right) arenes. B) Calculated spin densi...
Figure 39: A) Recycling e-PRC C(sp2 )–H acetoxylation of arenes using DDQ as a photocatalyst. B) Proposed cata...
Figure 40: Gram scale hydroxylation of benzene in a recirculated flow setup.
Figure 41: A) Radical ion e-PRC vicinal diamination of alkylarenes using TAC+ as an electro-activated photocat...
Figure 42: A) Sequential oxygenation of multiple adjacent C–H bonds under radical ion e-PRC using TAC+ as an e...
Figure 43: A) Enantioselective recycling e-PRC cyanation of benzylic C–H bonds using ADQS as photocatalyst. B)...
Figure 44: Proposed tandem mechanism by Xu and co-workers.
Figure 45: A) Enantioselective recycling e-PRC decarboxylative cyanation using Cu(acac)2, Ce(OTf)3 and a box l...
Figure 46: A) Enantioselective recycling e-PRC benzylic cyanation using Cu(MeCN)4BF4, box ligand and anthraqui...
Figure 47: A) Radical ion e-PRC acetoxyhydroxylation of aryl olefins using TAC+ as an electro-activated photoc...
Figure 48: Selected examples from the substrate scope.
Figure 49: Photoelectrochemical acetoxyhydroxylation in a recirculated flow setup.
Figure 50: A) Radical ion e-PRC aminooxygenation of aryl olefins using TAC+ as an electro-activated photocatal...
Figure 51: A) Recycling e-PRC C–H alkylation of heteroarenes with organic trifluoroborates using Mes-Acr+ as p...
Figure 52: A) Recycling e-PRC decarboxylative C–H alkylation of heteroarenes using CeCl3·7H2O as catalyst. B) ...
Figure 53: A) Recycling e-PRC decarboxylative C–H alkylation of heteroarenes using Fe(NH4)2(SO4)2·6H2O as cata...
Figure 54: A) Recycling e-PRC C–H alkylation of heteroarenes with alkyl oxalates and 4CzIPN as photocatalyst. ...
Figure 55: A) Recycling e-PRC decarboxylative C–H carbamoylation of heteroarenes using 4CzIPN as photocatalyst...
Figure 56: A) Photoelectrochemical HAT-mediated hydrocarbon activation via the chlorine radical. B) Proposed m...
Figure 57: A) Selected examples from the substrate scope. B) Gram and decagram scale semi-continuous flow PEC ...
Figure 58: A) Photoelectrochemical HAT-mediated dehydrogenative coupling of benzothiazoles with aliphatic C–H ...
Figure 59: A) Photoelectrochemical HAT activation of ethers using electro-activated TAC+ as photocatalyst. B) ...
Figure 60: Selected examples from the substrate scope.
Figure 61: A) Photoelectrochemical HAT-mediated synthesis of alkylated benzimidazo-fused isoquinolinones using...
Figure 62: A) Decoupled photoelectrochemical cerium-catalyzed oxydichlorination of alkynes using CeCl3 as cata...
Figure 63: Proposed decoupled photoelectrochemical mechanism.
Figure 64: A) Decoupled photoelectrochemical ring-opening bromination of tertiary cycloalkanols using MgBr2 as...
Figure 65: A) Recycling e-PRC ring-opening functionalization of cycloalkanols using CeCl3 as catalyst. B) Prop...
Figure 66: Selected examples from the substrate scope of the PEC ring-opening functionalization.
Figure 67: A) Radical ion e-PRC reduction of chloro- and bromoarenes using DCA as catalyst and various accepto...
Figure 68: A) Screening of different phthalimide derivatives as catalyst for the e-PRC reduction of aryl halid...
Figure 69: Screening of different organic catalysts for the e-PRC reduction of trialkylanilium salts.
Figure 70: A) e-PRC reduction of phosphonated phenols and anilinium salts. B) Selected examples from the subst...
Figure 71: A) ConPET and e-PRC reduction of 4-bromobenzonitrile using a naphthalene diimide (NDI) precatalyst ...
Figure 72: A) Radical ion e-PRC reduction of phosphinated aliphatic alcohols with n-BuO-NpMI as catalyst. B) C...
Figure 73: Selected examples from the substrate scope.
Figure 74: A) Recycling e-PRC reductive dimerization of benzylic chlorides using a [Cu2] catalyst. B) Proposed...
Figure 75: A) Decoupled photoelectrochemical C–H alkylation of heteroarenes through deamination of Katritzky s...
Figure 76: Proposed mechanism by Chen and co-workers.
Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines
- Dmitry B. Vinogradov,
- Alexei N. Izmest’ev,
- Angelina N. Kravchenko,
- Yuri A. Strelenko and
- Galina A. Gazieva
Beilstein J. Org. Chem. 2023, 19, 1047–1054, doi:10.3762/bjoc.19.80
- rearrangement; 1,3-thiazines; thiazolidine-4-ones; Introduction Nitrogen- and sulfur-containing heterocyclic compounds are widely represented in nature and used for the synthesis of biologically active substances. Among the 1,3-thiazine derivatives, promising compounds as antimicrobial and antiviral drugs
Graphical Abstract
Figure 1: Examples of natural and synthetic bioactive 1,3-thiazine and imidazothiazolotriazine derivatives wi...
Scheme 1: Base-induced transformations and rearrangements of functionalized imidazo[4,5-e]thiazolo[3,2-b]-1,2...
Scheme 2: Alkaline hydrolysis of esters 1a,b. aDetermined by 1H NMR spectroscopy; bisolated yields.
Scheme 3: Synthesis of potassium imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazine-7-carboxylates.
Scheme 4: Plausible rearrangement mechanism of imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine 1d into imidazo[4...
Figure 2: 1H NMR spectra of the starting compound 1d (a) and the reaction mixture after 1.5 (b) and 4 (c) hou...
Scheme 5: Synthetic approaches to imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines 3a–d,j.
Scheme 6: Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazine-7-carboxylic acids 5a–j.
Scheme 7: Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazine-7-carboxylic acids 5k,m.
Scheme 8: Plausible path for the formation of products 9.
Figure 3: 1H NMR spectra of compounds 4a and 5a in DMSO-d6 in the region of 4.3–9.0 ppm.
Figure 4: 13C NMR GATED spectra of compounds 4a and 5a in DMSO-d6 in the region of 156.0–168.0 ppm.
Figure 5: General view of 5a in the crystal in thermal ellipsoid representation (p = 80%).
Synthesis of aliphatic nitriles from cyclobutanone oxime mediated by sulfuryl fluoride (SO2F2)
- Xian-Lin Chen and
- Hua-Li Qin
Beilstein J. Org. Chem. 2023, 19, 901–908, doi:10.3762/bjoc.19.68
- fluoride; SO2F2; Introduction As an important functional group in organic molecules, the nitrile group is commonly present in functional materials [1][2], nanoscale drug carriers [3][4][5], biologically valuable molecules and drugs (Scheme 1) [6][7]. There are over 70 nitrile-containing drugs approved by
Graphical Abstract
Scheme 1: Representative nitrile-containing functional materials, drug carriers, and medicines.
Scheme 2: Activating protocol of cyclobutanone oximes.
Scheme 3: Substrate scope of δ-olefin-containing aliphatic nitriles. Reaction conditions: A mixture of cyclob...
Scheme 4: Competition between two reactions caused by the reduction of base equivalent.
Scheme 5: Mechanistic investigations.
Scheme 6: A proposed plausible mechanism.
Pyridine C(sp2)–H bond functionalization under transition-metal and rare earth metal catalysis
- Haritha Sindhe,
- Malladi Mounika Reddy,
- Karthikeyan Rajkumar,
- Akshay Kamble,
- Amardeep Singh,
- Anand Kumar and
- Satyasheel Sharma
Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62
Graphical Abstract
Figure 1: Representative examples of bioactive natural products and FDA-approved drugs containing a pyridine ...
Scheme 1: Classical and traditional methods for the synthesis of functionalized pyridines.
Scheme 2: Rare earth metal (Ln)-catalyzed pyridine C–H alkylation.
Scheme 3: Pd-catalyzed C–H alkylation of pyridine N-oxide.
Scheme 4: CuI-catalyzed C–H alkylation of N-iminopyridinium ylides with tosylhydrazones (A) and a plausible r...
Scheme 5: Zirconium complex-catalyzed pyridine C–H alkylation.
Scheme 6: Rare earth metal-catalyzed pyridine C–H alkylation with nonpolar unsaturated substrates.
Scheme 7: Heterobimetallic Rh–Al complex-catalyzed ortho-C–H monoalkylation of pyridines.
Scheme 8: Mono(phosphinoamido)-rare earth complex-catalyzed pyridine C–H alkylation.
Scheme 9: Rhodium-catalyzed pyridine C–H alkylation with acrylates and acrylamides.
Scheme 10: Ni–Al bimetallic system-catalyzed pyridine C–H alkylation.
Scheme 11: Iridium-catalyzed pyridine C–H alkylation.
Scheme 12: para-C(sp2)–H Alkylation of pyridines with alkenes.
Scheme 13: Enantioselective pyridine C–H alkylation.
Scheme 14: Pd-catalyzed C2-olefination of pyridines.
Scheme 15: Ru-catalyzed C-6 (C-2)-propenylation of 2-arylated pyridines.
Scheme 16: C–H addition of allenes to pyridines catalyzed by half-sandwich Sc metal complex.
Scheme 17: Pd-catalyzed stereodivergent synthesis of alkenylated pyridines.
Scheme 18: Pd-catalyzed ligand-promoted selective C3-olefination of pyridines.
Scheme 19: Mono-N-protected amino acids in Pd-catalyzed C3-alkenylation of pyridines.
Scheme 20: Amide-directed and rhodium-catalyzed C3-alkenylation of pyridines.
Scheme 21: Bimetallic Ni–Al-catalyzed para-selective alkenylation of pyridine.
Scheme 22: Arylboronic ester-assisted pyridine direct C–H arylation.
Scheme 23: Pd-catalyzed C–H arylation/benzylation with toluene.
Scheme 24: Pd-catalyzed pyridine C–H arylation with potassium aryl- and heteroaryltrifluoroborates.
Scheme 25: Transient activator strategy in pyridine C–H biarylation.
Scheme 26: Ligand-promoted C3-arylation of pyridine.
Scheme 27: Pd-catalyzed arylation of nicotinic and isonicotinic acids.
Scheme 28: Iron-catalyzed and imine-directed C–H arylation of pyridines.
Scheme 29: Pd–(bipy-6-OH) cooperative system-mediated direct pyridine C3-arylation.
Scheme 30: Pd-catalyzed pyridine N-oxide C–H arylation with heteroarylcarboxylic acids.
Scheme 31: Pd-catalyzed C–H cross-coupling of pyridine N-oxides with five-membered heterocycles.
Scheme 32: Cu-catalyzed dehydrative biaryl coupling of azine(pyridine) N-oxides and oxazoles.
Scheme 33: Rh(III)-catalyzed cross dehydrogenative C3-heteroarylation of pyridines.
Scheme 34: Pd-catalyzed C3-selective arylation of pyridines.
Scheme 35: Rhodium-catalyzed oxidative C–H annulation of pyridines to quinolines.
Scheme 36: Rhodium-catalyzed and NHC-directed C–H annulation of pyridine.
Scheme 37: Ni/NHC-catalyzed regio- and enantioselective C–H cyclization of pyridines.
Scheme 38: Rare earth metal-catalyzed intramolecular C–H cyclization of pyridine to azaindolines.
Scheme 39: Rh-catalyzed alkenylation of bipyridine with terminal silylacetylenes.
Scheme 40: Rollover cyclometallation in Rh-catalyzed pyridine C–H functionalization.
Scheme 41: Rollover pathway in Rh-catalyzed C–H functionalization of N,N,N-tridentate chelating compounds.
Scheme 42: Pd-catalyzed rollover pathway in bipyridine-6-carboxamides C–H arylation.
Scheme 43: Rh-catalyzed C3-acylmethylation of bipyridine-6-carboxamides with sulfoxonium ylides.
Scheme 44: Rh-catalyzed C–H functionalization of bipyridines with alkynes.
Scheme 45: Rh-catalyzed C–H acylmethylation and annulation of bipyridine with sulfoxonium ylides.
Scheme 46: Iridium-catalyzed C4-borylation of pyridines.
Scheme 47: C3-Borylation of pyridines.
Scheme 48: Pd-catalyzed regioselective synthesis of silylated dihydropyridines.
Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones
- Ksenia Malkova,
- Andrey Bubyrev,
- Stanislav Kalinin and
- Dmitry Dar’in
Beilstein J. Org. Chem. 2023, 19, 800–807, doi:10.3762/bjoc.19.60
- linker or pharmacophore group. In fact, more than one hundred FDA-approved drugs are sulfonamide-bearing small molecules. Screening libraries of aromatic and heteroaromatic sulfonamides gave rise to the discovery of multiple physiologically active compounds [27][28][29][30] including important
- pathway to 2-alkoxyquinolines. a) Conventional drugs containing either a sulfonamide fragment or a quinoline core; b) biologically active quinoline sulfonamides. Knoevenagel condensation/aza-Wittig reaction cascade for the quinoline core formation. Key reaction steps during the synthesis of 3-sulfonyl
Graphical Abstract
Figure 1: a) Conventional drugs containing either a sulfonamide fragment or a quinoline core; b) biologically...
Figure 2: Knoevenagel condensation/aza-Wittig reaction cascade for the quinoline core formation.
Scheme 1: Key reaction steps during the synthesis of 3-sulfonyl-substituted quinolines.
Scheme 2: Synthetic routes to sulfonamides and sulfones 2 and the set of reagents for the preparation of comp...
Scheme 3: Preparation of 3-sulfonyl substituted quinolines 5a–q.
Scheme 4: 3-Sulfonyl-substituted quinolines 5r–v that failed to be synthesized.
Synthesis of imidazo[1,2-a]pyridine-containing peptidomimetics by tandem of Groebke–Blackburn–Bienaymé and Ugi reactions
- Oleksandr V. Kolomiiets,
- Alexander V. Tsygankov,
- Maryna N. Kornet,
- Aleksander A. Brazhko,
- Vladimir I. Musatov and
- Valentyn A. Chebanov
Beilstein J. Org. Chem. 2023, 19, 727–735, doi:10.3762/bjoc.19.53
- , isocyanide multicomponent reactions are the way to prepare the necessary drugs "of tomorrow", and the possibility to combine such reactions gives a powerful method to rapidly and qualitatively expand the molecular diversity of biologically active compounds. The following possible combinations of IMCR have
- be used as potential drug candidate against Alzheimer's disease [14]. Compounds containing the imidazo[1,2-a]pyridine moiety are present in many natural products and marketed drugs, e.g., alpidem (an anxiolytic) [15], necopidem (anxiolytic) [16], zolpidem (hypnotic for the treatment of insomnia) [17
- ], olprinon (cardiotonic agent for the treatment of acute heart failure) [18], GSK812397 (with anti-human immunodeficiency virus (HIV) properties) [19] (Figure 1). In light of the numerous viral epidemics and even pandemics, antiviral drugs that can inhibit the activity of proteins and enzymes encoded by
Graphical Abstract
Scheme 1: Diversity of structures synthesized by combining IMCR’s.
Figure 1: Drugs possessing imidazo[1,2-a]pyridine unit.
Figure 2: Drugs possessing peptide unit.
Scheme 2: Diversity of GBB reaction products as precursors for Ugi reaction.
Scheme 3: Synthesis of new acids containing a substituted imidazo[1,2-a]pyridine fragment.
Scheme 4: Synthesis of new peptidomimetics containing a substituted imidazo[1,2-a]pyridine fragment.
Scheme 5: Synthesis and reactivity of new acids containing a substituted imidazo[1,2-a]pyridine fragment with...
Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates
- Bastian Jakob,
- Nico Schneider,
- Luca Gengenbach and
- Georg Manolikakes
Beilstein J. Org. Chem. 2023, 19, 719–726, doi:10.3762/bjoc.19.52
- production of drugs, fertilizers, (biodegradable) polymers or nutritional supplements [2]. More importantly, α-amino acids form the backbone of all proteins and enzymes are therefore essential for almost all biological processes. In the last twenty years non-proteinogenic and chemically synthesized unnatural
- several well-known natural products with interesting biological properties, such as the glycopeptide antibiotics vancomycin and teicoplanin [5] or feglymycin [6], a 13mer peptide which contains nine α-arylglycines in its backbone. α-Arylglycine derivatives are used in the production of important drugs
Graphical Abstract
Figure 1: Biologically active molecules containing α-arylglycine motifs (highlighted in green and blue).
Scheme 1: The Petasis reaction – fundamental reactivities and recent developments.
Scheme 2: Observations from previous studies and mechanistic rationale.
Scheme 3: Initial experiments.
Scheme 4: Reaction scope – aryltrifluoroborates (yields and enantiomeric ratios in parentheses refer to our p...
Scheme 5: Synthesis of both enantiomers of arylglycine building block 18.
Transition-metal-catalyzed domino reactions of strained bicyclic alkenes
- Austin Pounder,
- Eric Neufeld,
- Peter Myler and
- William Tam
Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38
Graphical Abstract
Figure 1: Ring-strain energies of homobicyclic and heterobicyclic alkenes in kcal mol−1. a) [2.2.1]-Bicyclic ...
Figure 2: a) Exo and endo face descriptions of bicyclic alkenes. b) Reactivity comparisons for different β-at...
Scheme 1: Ni-catalyzed ring-opening/cyclization cascade of heterobicyclic alkenes 1 with alkyl propiolates 2 ...
Scheme 2: Ni-catalyzed ring-opening/cyclization cascade of heterobicyclic alkenes 8 with β-iodo-(Z)-propenoat...
Scheme 3: Ni-catalyzed two- and three-component difunctionalizations of norbornene derivatives 15 with alkyne...
Scheme 4: Ni-catalyzed intermolecular three-component difunctionalization of oxabicyclic alkenes 1 with alkyn...
Scheme 5: Ni-catalyzed intermolecular three-component carboacylation of norbornene derivatives 15.
Scheme 6: Photoredox/Ni dual-catalyzed coupling of 4-alkyl-1,4-dihydropyridines 31 with heterobicyclic alkene...
Scheme 7: Photoredox/Ni dual-catalyzed coupling of α-amino radicals with heterobicyclic alkenes 30.
Scheme 8: Cu-catalyzed rearrangement/allylic alkylation of 2,3-diazabicyclo[2.2.1]heptenes 47 with Grignard r...
Scheme 9: Cu-catalyzed aminoboration of bicyclic alkenes 1 with bis(pinacolato)diboron (B2pin2) (53) and O-be...
Scheme 10: Cu-catalyzed borylalkynylation of oxabenzonorbornadiene (30b) with B2pin2 (53) and bromoalkynes 62.
Scheme 11: Cu-catalyzed borylacylation of bicyclic alkenes 1.
Scheme 12: Cu-catalyzed diastereoselective 1,2-difunctionalization of oxabenzonorbornadienes 30 for the synthe...
Scheme 13: Fe-catalyzed carbozincation of heterobicyclic alkenes 1 with arylzinc reagents 74.
Scheme 14: Co-catalyzed addition of arylzinc reagents of norbornene derivatives 15.
Scheme 15: Co-catalyzed ring-opening/dehydration of oxabicyclic alkenes 30 via C–H activation of arenes.
Scheme 16: Co-catalyzed [3 + 2] annulation/ring-opening/dehydration domino reaction of oxabicyclic alkenes 1 w...
Scheme 17: Co-catalyzed enantioselective carboamination of bicyclic alkenes 1 via C–H functionalization.
Scheme 18: Ru-catalyzed cyclization of oxabenzonorbornene derivatives with propargylic alcohols for the synthe...
Scheme 19: Ru-catalyzed coupling of oxabenzonorbornene derivatives 30 with propargylic alcohols and ethers 106...
Scheme 20: Ru-catalyzed ring-opening/dehydration of oxabicyclic alkenes via the C–H activation of anilides.
Scheme 21: Ru-catalyzed of azabenzonorbornadiene derivatives with arylamides.
Scheme 22: Rh-catalyzed cyclization of bicyclic alkenes with arylboronate esters 118.
Scheme 23: Rh-catalyzed cyclization of bicyclic alkenes with dienyl- and heteroaromatic boronate esters.
Scheme 24: Rh-catalyzed domino lactonization of doubly bridgehead-substituted oxabicyclic alkenes with seconda...
Scheme 25: Rh-catalyzed domino carboannulation of diazabicyclic alkenes with 2-cyanophenylboronic acid and 2-f...
Scheme 26: Rh-catalyzed synthesis of oxazolidinone scaffolds 147 through a domino ARO/cyclization of oxabicycl...
Scheme 27: Rh-catalyzed oxidative coupling of salicylaldehyde derivatives 151 with diazabicyclic alkenes 130a.
Scheme 28: Rh-catalyzed reaction of O-acetyl ketoximes with bicyclic alkenes for the synthesis of isoquinoline...
Scheme 29: Rh-catalyzed domino coupling reaction of 2-phenylpyridines 165 with oxa- and azabicyclic alkenes 30....
Scheme 30: Rh-catalyzed domino dehydrative naphthylation of oxabenzonorbornadienes 30 with N-sulfonyl 2-aminob...
Scheme 31: Rh-catalyzed domino dehydrative naphthylation of oxabenzonorbornadienes 30 with arylphosphine deriv...
Scheme 32: Rh-catalyzed domino ring-opening coupling reaction of azaspirotricyclic alkenes using arylboronic a...
Scheme 33: Tandem Rh(III)/Sc(III)-catalyzed domino reaction of oxabenzonorbornadienes 30 with alkynols 184 dir...
Scheme 34: Rh-catalyzed asymmetric domino cyclization and addition reaction of 1,6-enynes 194 and oxa/azabenzo...
Scheme 35: Rh/Zn-catalyzed domino ARO/cyclization of oxabenzonorbornadienes 30 with phosphorus ylides 201.
Scheme 36: Rh-catalyzed domino ring opening/lactonization of oxabenzonorbornadienes 30 with 2-nitrobenzenesulf...
Scheme 37: Rh-catalyzed domino C–C/C–N bond formation of azabenzonorbornadienes 30 with aryl-2H-indazoles 210.
Scheme 38: Rh/Pd-catalyzed domino synthesis of indole derivatives with 2-(phenylethynyl)anilines 212 and oxabe...
Scheme 39: Rh-catalyzed domino carborhodation of heterobicyclic alkenes 30 with B2pin2 (53).
Scheme 40: Rh-catalyzed three-component 1,2-carboamidation reaction of bicyclic alkenes 30 with aromatic and h...
Scheme 41: Pd-catalyzed diarylation and dialkenylation reactions of norbornene derivatives.
Scheme 42: Three-component Pd-catalyzed arylalkynylation reactions of bicyclic alkenes.
Scheme 43: Three-component Pd-catalyzed arylalkynylation reactions of norbornene and DFT mechanistic study.
Scheme 44: Pd-catalyzed three-component coupling N-tosylhydrazones 236, aryl halides 66, and norbornene (15a).
Scheme 45: Pd-catalyzed arylboration and allylboration of bicyclic alkenes.
Scheme 46: Pd-catalyzed, three-component annulation of aryl iodides 66, alkenyl bromides 241, and bicyclic alk...
Scheme 47: Pd-catalyzed double insertion/annulation reaction for synthesizing tetrasubstituted olefins.
Scheme 48: Pd-catalyzed aminocyclopropanation of bicyclic alkenes 1 with 5-iodopent-4-enylamine derivatives 249...
Scheme 49: Pd-catalyzed, three-component coupling of alkynyl bromides 62 and norbornene derivatives 15 with el...
Scheme 50: Pd-catalyzed intramolecular cyclization/ring-opening reaction of heterobicyclic alkenes 30 with 2-i...
Scheme 51: Pd-catalyzed dimer- and trimerization of oxabenzonorbornadiene derivatives 30 with anhydrides 268.
Scheme 52: Pd-catalyzed Catellani-type annulation and retro-Diels–Alder of norbornadiene 15b yielding fused xa...
Scheme 53: Pd-catalyzed hydroarylation and heteroannulation of urea-derived bicyclic alkenes 158 and aryl iodi...
Scheme 54: Access to fused 8-membered sulfoximine heterocycles 284/285 via Pd-catalyzed Catellani annulation c...
Scheme 55: Pd-catalyzed 2,2-bifunctionalization of bicyclic alkenes 1 generating spirobicyclic xanthone deriva...
Scheme 56: Pd-catalyzed Catellani-type annulation and retro-Diels–Alder of norbornadiene (15b) producing subst...
Scheme 57: Pd-catalyzed [2 + 2 + 1] annulation furnishing bicyclic-fused indanes 281 and 283.
Scheme 58: Pd-catalyzed ring-opening/ring-closing cascade of diazabicyclic alkenes 130a.
Scheme 59: Pd-NHC-catalyzed cyclopentannulation of diazabicyclic alkenes 130a.
Scheme 60: Pd-catalyzed annulation cascade generating diazabicyclic-fused indanones 292 and indanols 294.
Scheme 61: Pd-catalyzed skeletal rearrangement of spirotricyclic alkenes 176 towards large polycyclic benzofur...
Scheme 62: Pd-catalyzed oxidative annulation of aromatic enamides 298 and diazabicyclic alkenes 130a.
Scheme 63: Accessing 3,4,5-trisubstituted cyclopentenes 300, 301, 302 via the Pd-catalyzed domino reaction of ...
Scheme 64: Palladacycle-catalyzed ring-expansion/cyclization domino reactions of terminal alkynes and bicyclic...
Scheme 65: Pd-catalyzed carboesterification of norbornene (15a) with alkynes, furnishing α-methylene γ-lactone...
Total synthesis: an enabling science
- Bastien Nay
Beilstein J. Org. Chem. 2023, 19, 474–476, doi:10.3762/bjoc.19.36
- the construction of complex molecules [10][11]. Incidentally, the term "total synthesis" is not limited to natural products but also, sometimes, targets complex drugs [12][13]. Furthermore, it is possible to test biosynthetic hypotheses concerning natural products through synthetic approaches
Graphical Abstract
Figure 1: A summary of compounds targeted in this thematic issue.
Transition-metal-catalyzed C–H bond activation as a sustainable strategy for the synthesis of fluorinated molecules: an overview
- Louis Monsigny,
- Floriane Doche and
- Tatiana Besset
Beilstein J. Org. Chem. 2023, 19, 448–473, doi:10.3762/bjoc.19.35
- -fluorinated molecules [1][2], their incorporation in various scaffolds afforded high value-added compounds as demonstrated by their numerous applications in the industrial sector such as drugs, agrochemicals, and materials. To further illustrate the ubiquity of fluorinated compounds, almost 20% of
Graphical Abstract
Scheme 1: Transition-metal-catalyzed C–XRF bond formation by C–H bond activation: an overview.
Scheme 2: Cu(OAc)2-promoted mono- and ditrifluoromethylthiolation of benzamide derivatives derived from 8-ami...
Scheme 3: Trifluoromethylthiolation of azacalix[1]arene[3]pyridines using copper salts and a nucleophilic SCF3...
Scheme 4: Working hypothesis for the palladium-catalyzed C–H trifluoromethylthiolation reaction.
Scheme 5: Trifluoromethylthiolation of 2-arylpyridine derivatives and analogs by means of palladium-catalyzed...
Scheme 6: C(sp2)–SCF3 bond formation by Pd-catalyzed C–H bond activation using AgSCF3 and Selectfluor® as rep...
Scheme 7: Palladium-catalyzed ortho-trifluoromethylthiolation of 2-arylpyridine derivatives reported by the g...
Scheme 8: Palladium-catalyzed ortho-trifluoromethylthiolation of 2-arylpyridine and analogs reported by Anbar...
Scheme 9: Mono- and ditrifluoromethylthiolation of benzamide derivatives derived from 8-aminoquinoline using ...
Scheme 10: Regioselective Cp*Rh(III)-catalyzed directed trifluoromethylthiolation reported by the group of Li [123]...
Scheme 11: Cp*Co(III)-catalyzed ortho-trifluoromethylthiolation of 2-phenylpyridine and 2-phenylpyrimidine der...
Scheme 12: Cp*Co(III)-catalyzed ortho-trifluoromethylthiolation of 2-phenylpyridine and 6-phenylpurine derivat...
Scheme 13: Diastereoselective trifluoromethylthiolation of acrylamide derivatives derived from 8-aminoquinolin...
Scheme 14: C(sp3)–SCF3 bond formation on aliphatic amide derivatives derived from 8-aminoquinoline by palladiu...
Scheme 15: Regio- and diastereoselective difluoromethylthiolation of acrylamides under palladium catalysis rep...
Scheme 16: Palladium-catalyzed (ethoxycarbonyl)difluoromethylthiolation reaction of 2-(hetero)aryl and 2-(α-ar...
Scheme 17: Pd(II)-catalyzed trifluoromethylselenolation of benzamides derived from 5-methoxy-8-aminoquinoline ...
Scheme 18: Pd(II)-catalyzed trifluoromethylselenolation of acrylamide derivatives derived from 5-methoxy-8-ami...
Scheme 19: Transition-metal-catalyzed dehydrogenative 2,2,2-trifluoroethoxylation of (hetero)aromatic derivati...
Scheme 20: Pd(II)-catalyzed ortho-2,2,2-trifluoroethoxylation of N-sulfonylbenzamides reported by the group of...
Scheme 21: Pd(II)-catalyzed selective 2,2,2-trifluoroethoxylation and other fluoroalkoxylations of naphthalene...
Scheme 22: Pd(II)-catalyzed selective ortho-2,2,2-trifluoroethoxylation of benzaldehyde derivatives by means o...
Scheme 23: Pd(II)-catalyzed selective ortho-2,2,2-trifluoroethoxylation (and other fluoroalkoxylations) of ben...
Scheme 24: Pd(II)-catalyzed selective 2,2,2-trifluoroethoxylation of aliphatic amides using a bidentate direct...
Dipeptide analogues of fluorinated aminophosphonic acid sodium salts as moderate competitive inhibitors of cathepsin C
- Karolina Wątroba,
- Małgorzata Pawełczak and
- Marcin Kaźmierczak
Beilstein J. Org. Chem. 2023, 19, 434–439, doi:10.3762/bjoc.19.33
- in chemotherapies to support traditional anticancer drugs. Moreover, there is a growing interest in the topic of cathepsin C inhibition, which directly affects serine protease activity [5][6]. Inhibitors of cathepsin C can be cystatins that show activity against a large group of cysteine proteases [7
Graphical Abstract
Scheme 1: Synthetic strategy towards 5 and 7.
Scheme 2: Synthesis of 9 and 11. (a) R = -CH3; (b) R = -CH(CH3)2; (c) R = -CH2CH(CH3)2; (d) R = -CH(CH3)CH2CH3...
Figure 1: Dixon plot for the hydrolysis of Gly-Phe-pNA substrate catalyzed by bovine cathepsin C in the prese...
Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities
- Jorge de Lima Neto and
- Paulo Henrique Menezes
Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31
- bond of 28 leads to compounds of increasing activity, being the more polar hydroxy-substituted derivatives the most active (Table 2) [73]. One of the major obstacles in the development of highly potent drugs is the water solubility. Pettit and co-workers [55] conducted an extensive study in an attempt
Graphical Abstract
Figure 1: Structures of some members of the combretastatin D series, corniculatolides, and isocorniculatolide...
Scheme 1: Biosynthetic pathway proposed by Pettit and co-workers.
Scheme 2: Biosynthetic pathway towards corniculatolides or isocorniculatolides proposed by Ponnapalli and co-...
Scheme 3: Retrosynthetic approaches.
Scheme 4: Attempt of total synthesis of 2 by Boger and co-workers employing the Mitsunobu approach [27].
Scheme 5: Total synthesis of combretastatin D-2 (2) reported by Boger and co-workers employing an intramolecu...
Scheme 6: Formal synthesis of combretastatin D-2 (2) by Deshpande and co-workers using the Mitsunobu conditio...
Scheme 7: Total synthesis of combretastatin D-2 (2) by Rychnovsky and Hwang [36].
Scheme 8: Divergent synthesis of (±)-1 form combretastatin D-2 (2) by Rychnovsky and Hwang [36].
Scheme 9: Enantioselective synthesis of 1 by Rychnovsky and Hwang employing Jacobsen catalyst [41].
Scheme 10: Synthesis of fragment 57 by Couladouros and co-workers [43,45].
Scheme 11: Formal synthesis of compound 2 by Couladouros and co-workers [43,45].
Scheme 12: Synthesis of fragment 66 by Couladouros and co-workers [44,45].
Scheme 13: Synthesis of fragment 70 by Couladouros and co-workers [44,45].
Scheme 14: Synthesis of fragment 77 by Couladouros and co-workers [44,45].
Scheme 15: Synthesis of combretastatins 1 and 2 by Couladouros and co-workers [44,45].
Scheme 16: Formal synthesis of compound 2 by Gangakhedkar and co-workers [48].
Scheme 17: Synthesis of fragment 14 by Cousin and co-workers [50].
Scheme 18: Synthesis of fragment 91 by Cousin and co-workers [50].
Scheme 19: Formal synthesis of compound 2 by Cousin and co-workers [50].
Scheme 20: Synthesis of 2 diolide by Cousin and co-workers [50].
Scheme 21: Synthesis of combretastatin D-4 (4) by Nishiyama and co-workers [54].
Scheme 22: Synthesis of fragment 112 by Pettit and co-workers [55].
Scheme 23: Synthesis of fragment 114 by Pettit and co-workers [55].
Scheme 24: Attempt to the synthesis of compound 2 by Pettit and co-workers [55].
Scheme 25: Synthesis of combretastatin-D2 (2) starting from isovanilin (80) by Pettit and co-workers [55].
Scheme 26: Attempted synthesis of combretastatin-D2 (2) derivatives through an SNAr approach [55].
Scheme 27: Synthesis of combretastatin D-4 (4) by Pettit and co-workers [55].
Scheme 28: Synthesis of combretastatin D-2 (2) by Harras and co-workers [57].
Scheme 29: Synthesis of combretastatin D-4 (4) by Harras and co-workers [57].
Scheme 30: Formal synthesis of combretastatin D-1 (1) by Harras and co-workers [57].
Scheme 31: Synthesis of 11-O-methylcorniculatolide A (5) by Raut and co-workers [69].
Scheme 32: Synthesis of isocorniculatolide A (7) and O-methylated isocorniculatolide A 8 by Raut and co-worker...
Scheme 33: Synthesis of isocorniculatolide B (10) and hydroxyisocorniculatolide B 175 by Kim and co-workers [71].
Scheme 34: Synthesis of compound 9, 178, and 11 by Kim and co-workers [71].
Scheme 35: Synthesis of combretastatin D-2 prodrug salts [55].
Figure 2: ED50 values of the combretastatin D family against murine P388 lymphocytic leukemia cell line (appr...
Figure 3: IC50 of compounds against α-glucosidase [19].
Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis
- Nicoleta G. Hădărugă,
- Gabriela Popescu,
- Dina Gligor (Pane),
- Cristina L. Mitroi,
- Sorin M. Stanciu and
- Daniel Ioan Hădărugă
Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30
- -based ternary complexes, but they do not deal with triglyceride-based vegetable oils or with flavonoid glycosides/flavonolignans. Most of these studies are related to controlled release of various drugs from the CD complexes such as diosmin and polyethylene glycol, haloperidol and lactic acid
Graphical Abstract
Figure 1: Hypothetical interactions between the β-cyclodextrin host and guest molecules (flavonoid glycoside/...
Figure 2: Superposition of the FTIR spectra for the β-cyclodextrin/Corylus avellana oil/hesperidin ternary co...
Figure 3: Superposition of the FTIR spectra for the β-cyclodextrin/Corylus avellana oil/hesperidin ternary co...
Figure 4: PC2 versus PC1 scores plot from the FTIR–PCA analysis of the flavonoid glycoside and flavonolignan ...
Figure 5: PC2 versus PC1 scores plot from the FTIR–PCA analysis of the β-CD/hazelnut oil/flavonoid ternary co...
Figure 6: PC2 versus PC1 scores plot from the FTIR–PCA analysis of the β-CD/hazelnut oil/flavonoid ternary co...
Figure 7: PC2 versus PC1 scores plot from the FTIR–PCA analysis of the β-CD/hazelnut oil/flavonoid ternary co...
Figure 8: PC3 versus PC1 scores plot from the FTIR-PCA analysis of the β-CD/hazelnut oil/flavonoid ternary co...
Figure 9: PC3 versus PC2 scores plot from the FTIR–PCA analysis of the β-CD/hazelnut oil/flavonoid ternary co...
Figure 10: PC2 versus PC1 loadings plot from the FTIR–PCA analysis of the β-CD/hazelnut oil/flavonoid ternary ...
Figure 11: PC3 versus PC1 loadings plot from the FTIR–PCA analysis of the β-CD/hazelnut oil/flavonoid ternary ...
Figure 12: Eigenvalues of the correlation matrix from the FTIR–PCA analysis of the β-CD/hazelnut oil/flavonoid...
Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin
- János Máté Orosz,
- Dóra Ujj,
- Petr Kasal,
- Gábor Benkovics and
- Erika Bálint
Beilstein J. Org. Chem. 2023, 19, 294–302, doi:10.3762/bjoc.19.25
- complexation can lead to a significant solubility enhancement of poorly water-soluble molecules, and therefore it can enable the biological testing of drugs, which would otherwise not be possible by any other means [2][3]. Monosubstituted CDs contain only one hydroxy group modified with a functional group. In
Graphical Abstract
Scheme 1: Tosylation of β-CD under continuous flow conditions.
Scheme 2: Continuous flow azidation of Ts-β-CD (2).
Scheme 3: Continuous flow hydrogenation of N3-β-CD (3).
Scheme 4: Semi-continuous flow system for the synthesis of NH2-β-CD 4.
