Search for "thionyl chloride" in Full Text gives 87 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2019, 15, 852–857, doi:10.3762/bjoc.15.82
Graphical Abstract
Scheme 1: Synthesis of amino acid-based isocyanides starting from α-amino acids.
Scheme 2: Synthesis of pseudo-peptides using levulinic acid, isocyanide esters and amines.
Figure 1: Synthesis of functionalized 5-membered lactams using Ugi reaction. aIsolated yield for mixture of d...
Scheme 3: Proposed mechanism for Ugi-4C-3CR.
Figure 2: ORTEP representation of compound (R*,S*)-4a with thermal ellipsoids at 50% probability. Opposite en...
Beilstein J. Org. Chem. 2019, 15, 780–788, doi:10.3762/bjoc.15.74
Graphical Abstract
Scheme 1: Approach of the direct azologization of reported [60,61] serotonin 5-HT3R antagonists via replacement of a...
Scheme 2: Synthesis of the differently substituted quinoxaline azobenzene derivatives 5a and 5b via Baeyer [62]–M...
Scheme 3: Synthesis of the methoxy-substituted quinoxaline derivative 12a via diazotization [66-69].
Scheme 4: General procedure for the synthesis of purine- and thienopyrimidine-substituted arylazobenzenes and...
Scheme 5: Synthesis of the thiomethyl-linked purine azobenzene 23 [62,63,72-74].
Scheme 6: Synthesis of the amide-linked azobenzene purine 28 [62,63,75-77].
Figure 1: UV–vis absorption spectra measured at 50 µM in DMSO. Left: purine derivative 16c; right: azo-extend...
Figure 2: On the left panel representative traces of currents induced by the application of 3 µM 5HT (black t...
Beilstein J. Org. Chem. 2018, 14, 2002–2011, doi:10.3762/bjoc.14.175
Graphical Abstract
Figure 1: Examples of chiral bimetallic complexes utilized in asymmetric catalysis.
Figure 2: Previously reported bisoxazoline ligands capable of stabilizing bimetallic complexes.
Scheme 1: Synthesis of naphthyridine–bisoxazoline ligand 16-H2.
Figure 3: Thermal ellipsoid plot (50% probability) of the molecular structure of 16·Ni2(OAc)2. Hydrogen and s...
Scheme 2: Synthesis of naphthyridine–bisoxazoline ligand 22-H2.
Scheme 3: Synthesis of pyrazole–bisoxazoline ligand 25-H3.
Figure 4: Thermal ellipsoid plot (50% probability) of the molecular structure of 25·Ni2(OAc). Hydrogen and so...
Scheme 4: Synthesis of pyrazole–bisoxazoline ligand 30-H3.
Figure 5: Thermal ellipsoid plot (50% probability) of the molecular structure of 30·Pd2Br. Hydrogen and solva...
Scheme 5: Synthesis of pyridazine–bisoxazoline ligand 32-H2.
Figure 6: Thermal ellipsoid plot (50% probability) of the molecular structure of 32·Zn2Cl2. Hydrogen and solv...
Scheme 6: Synthesis of phenol–bisoxazoline ligand 34-H3.
Beilstein J. Org. Chem. 2018, 14, 1834–1839, doi:10.3762/bjoc.14.156
Graphical Abstract
Scheme 1: Reactions of aryl/hetarylthiochalcones 1a–d with 1,4-naphthoquinone (2b).
Scheme 2: Reactions of thiochalcones 1a–d with 1,4-anthraquinones 2c and 2d.
Figure 1: ORTEP plot [29] of the molecular structure of 4k showing the major conformation of the disordered thiop...
Figure 2: Products of the reactions of thiochalcones 1a and 1b with 1,4-benzoquinone (2a) and of 1a with mena...
Beilstein J. Org. Chem. 2018, 14, 1704–1722, doi:10.3762/bjoc.14.145
Graphical Abstract
Figure 1: The key elements for design and construction of the targeted G-2 dendrimers.
Scheme 1: Convergent versus divergent three steps (a–c) synthesis of central building blocks C1 and C3.
Scheme 2: Synthesis of G-1 dendrons D-Cl and D-N<P>NH. *As partial conversions of 1 into 2a and 2b based on t...
Scheme 3: Synthesis of G-2 dendrimers 4–6 by m-trimerisations of G-1 dendrons D-Cl and D-N<P>NH.
Scheme 4: Synthesis of G-2 dendrimers 7–9 by m-trimerisations of G-1 dendron D-N<P>NH.
Figure 2: The three terms rotamerism of G-0 dendrons 2a and 3 about the C(s-triazine)–N(exocyclic) partial do...
Figure 3: Comparative details from 1H NMR spectra of G-2 dendrimer 5 (500 MHz, 5.0 mM in DMSO-d6).
Figure 4: Comparative IR spectra (KBr) of compounds 7a vs 7b (a), 7b vs trimesic acid (b), 8 vs C1 (c) and 9 ...
Figure 5: 2D-1H-DOSY NMR charts (DMSO-d6, 500 MHz, 298 K) of compounds 7a, 7b (2.5 mM), 8 and 9 (5.0 mM).
Figure 6: The DFT optimised geometry at M062X/def2-TZVP level of theory of G-2 dendrimer 7a in DMSO (hydrogen...
Figure 7: The DFT optimised geometry at M062X/def2-TZVP level of theory of trimesic tris-carboxylate anion (a...
Figure 8: The DFT optimised geometry at M062X/def2-TZVP level of theory of G-2 dendrimers 8 and 9 in DMSO.
Figure 9: TEM images of homogeneously packed spherical nano-aggregates (a) and their agglomerations (b) in th...
Figure 10: TEM images of homogeneously packed spherical nano-aggregates (a) and their agglomerations (b) in th...
Figure 11: Proposed π-stacking interactions in compounds D-N<P>NH and 5–7a.
Beilstein J. Org. Chem. 2018, 14, 1287–1292, doi:10.3762/bjoc.14.110
Graphical Abstract
Scheme 1: Envisaged approach for the synthesis of 5-chloropyrazole-4-carboxylates 2.
Scheme 2: Synthesis of bipyrazolone 3a.
Figure 1: Signal of the OCH2 ester protons of reaction product 3a (500 MHz, CDCl3).
Figure 2: ORTEP-plot of the crystal structure of compound 3a drawn with 50% displacement ellipsoids [(4S,4'S)-...
Figure 3: Arrangement (4R,4'R)- and (4S,4'S)-3a enantiomers in the crystal unit drawn with 50% displacement e...
Scheme 3: Synthesis of compounds 3a–i.
Scheme 4: Reaction of different 5-hydroxypyrazoles with thionyl chloride.
Scheme 5: Reaction of 1a with sulfuryl chloride.
Scheme 6: Possible reaction mechanism for the transformation 1 → 3.
Scheme 7: Preparation of bipyrazoles 10.
Figure 4: 1H NMR (italics), 13C NMR (normal letters) and 15N NMR (in bold) chemical shifts of 3a (in CDCl3).
Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98
Graphical Abstract
Scheme 1: Tropone (1), tropolone (2) and their resonance structures.
Figure 1: Natural products containing a tropone nucleus.
Figure 2: Possible isomers 11–13 of benzotropone.
Scheme 2: Synthesis of benzotropones 11 and 12.
Scheme 3: Oxidation products of benzotropylium fluoroborate (16).
Scheme 4: Oxidation of 7-bromo-5H-benzo[7]annulene (22).
Scheme 5: Synthesis of 4,5-benzotropone (11) using o-phthalaldehyde (27).
Scheme 6: Synthesis of 4,5-benzotropone (11) starting from oxobenzonorbornadiene 31.
Scheme 7: Acid-catalyzed cleavage of oxo-bridge of 34.
Scheme 8: Synthesis of 4,5-benzotropone (11) from o-xylylene dibromide (38).
Scheme 9: Synthesis of 4,5-benzotropone (11) via the carbene adduct 41.
Scheme 10: Heck coupling strategy for the synthesis of 11.
Scheme 11: Synthesis of benzofulvalenes via carbonyl group of 4,5-benzotropone (11).
Figure 3: Some cycloheptatrienylium cations.
Scheme 12: Synthesis of condensation product 63 and its subsequent oxidative cyclization products.
Figure 4: A novel series of benzo[7]annulenes prepared from 4,5-benzotropone (11).
Scheme 13: Preparation of substituted benzo[7]annulene 72 using the Mukaiyama-Michael reaction.
Figure 5: Possible benzo[7]annulenylidenes 73–75.
Scheme 14: Thermal and photochemical decomposition of 7-diazo-7H-benzo[7]annulene (76) and the trapping of int...
Scheme 15: Synthesis of benzoheptafulvalene 86.
Scheme 16: Synthesis of 7-(diphenylmethylene)-7H-benzo[7]annulene (89).
Scheme 17: Reaction of 4,5-benzotropone (11) with dimethyl diazomethane.
Scheme 18: Synthesis of dihydrobenzomethoxyazocine 103.
Scheme 19: Synthesis and reducibility of benzo-homo-2-methoxyazocines.
Scheme 20: Synthesis of 4,5-benzohomotropones 104 and 115 from 4,5-benzotropones 11 and 113.
Scheme 21: A catalytic deuterogenation of 4,5-benzotropone (11) and synthesis of 5-monosubstituted benzo[7]ann...
Scheme 22: Synthesis of methyl benzo[7]annulenes 131 and 132.
Scheme 23: Ambident reactivity of halobenzo[7]annulenylium cations 133a/b.
Scheme 24: Preparation of benzo[7]annulenylidene–iron complexes 147.
Scheme 25: Synthesis of 1-ethynylbenzotropone (150) and the etheric compound 152 from 4,5-benzotropone (11) wi...
Scheme 26: Thermal decomposition of 4,5-benzotropone (11).
Scheme 27: Reaction of 4,5-benzotropone (11) with 1,2-ethanediol and 1,2-ethanedithiol.
Scheme 28: Conversions of 1-benzosuberone (162) to 2,3-benzotropone (12).
Scheme 29: Synthesis strategies for 2,3-bezotropone (12) using 1-benzosuberones.
Scheme 30: Oxidation-based synthesis of 2,3-benzotropone (12) via 1-benzosuberone (162).
Scheme 31: Synthesis of 2,3-benzotropone (12) from α-tetralone (171) via ring-expansion.
Scheme 32: Preparation of 2,3-benzotropone (12) by using of benzotropolone 174.
Figure 6: Benzoheptafulvenes as condensation products of 2,3-benzotropone (12).
Scheme 33: Conversion of 2,3-benzotropone (12) to tosylhydrazone salt 182 and gem-dichloride 187.
Figure 7: Benzohomoazocines 191–193 and benzoazocines 194–197.
Scheme 34: From 2,3-benzotropone (12) to carbonium ions 198–201.
Scheme 35: Cycloaddition reactions of 2,3-benzotropone (12).
Scheme 36: Reaction of 2,3-benzotropone (12) with various reagents and compounds.
Figure 8: 3,4-Benzotropone (13) and its resonance structure.
Scheme 37: Synthesis of 6,7-benzobicyclo[3.2.0]hepta-3,6-dien-2-one (230).
Figure 9: Photolysis and thermolysis products of 230.
Figure 10: Benzotropolones and their tautomeric structures.
Scheme 38: Synthesis strategies of 4,5-benzotropolone (238).
Scheme 39: Synthesis protocol for 2-hydroxy-4,5-benzotropone (238) using oxazole-benzo[7]annulene 247.
Figure 11: Some quinoxaline and pyrazine derivatives 254–256 prepared from 4,5-benzotropolone (238).
Scheme 40: Nitration product of 4,5-benzotropolone (238) and its isomerization to 1-nitro-naphthoic acid (259)....
Scheme 41: Synthesis protocol for 6-hydroxy-2,3-benzotropone (239) from benzosuberone (162).
Scheme 42: Various reactions via 6-hydroxy-2,3-benzotropone (239).
Scheme 43: Photoreaction of 6-hydroxy-2,3-benzotropone (239).
Scheme 44: Synthesis of 7-hydroxy-2,3-benzotropone (241) from benzosuberone (162).
Scheme 45: Synthesis strategy for 7-hydroxy-2,3-benzotropone (241) from ketone 276.
Scheme 46: Synthesis of 7-hydroxy-2,3-benzotropone (241) from β-naphthoquinone (280).
Scheme 47: Synthesis of 7-hydroxy-2,3-benzotropone (241) from bicyclic endoperoxide 213.
Scheme 48: Synthesis of 7-hydroxy-2,3-benzotropone (241) by ring-closing metathesis.
Figure 12: Various monosubstitution products 289–291 of 7-hydroxy-2,3-benzotropone (241).
Scheme 49: Reaction of 7-hydroxy-2,3-benzotropone (241) with various reagents.
Scheme 50: Synthesis of 4-hydroxy-2,3-benzotropones 174 and 304 from diketones 300/301.
Scheme 51: Catalytic hydrogenation of diketones 300 and 174.
Scheme 52: Synthesis of halo-benzotropones from alkoxy-naphthalenes 306, 307 and 310.
Figure 13: Unexpected byproducts 313–315 during synthesis of chlorobenzotropone 309.
Figure 14: Some halobenzotropones and their cycloadducts.
Scheme 53: Multisep synthesis of 2-chlorobenzotropone 309.
Scheme 54: A multistep synthesis of 2-bromo-benzotropone 26.
Scheme 55: A multistep synthesis of bromo-2,3-benzotropones 311 and 316.
Scheme 56: Oxidation reactions of 8-bromo-5H-benzo[7]annulene (329) with some oxidants.
Scheme 57: Synthesis of 2-bromo-4,5-benzotropone (26).
Scheme 58: Synthesis of 6-chloro-2,3-benzotropone (335) using LiCl and proposed intermediate 336.
Scheme 59: Reaction of 7-bromo-2,3-benzotropone (316) with methylamine.
Scheme 60: Reactions of bromo-2,3-benzotropones 26 and 311 with dimethylamine.
Scheme 61: Reactions of bromobenzotropones 311 and 26 with NaOMe.
Scheme 62: Reactions of bromobenzotropones 26 and 312 with t-BuOK in the presence of DPIBF.
Scheme 63: Cobalt-catalyzed reductive cross-couplings of 7-bromo-2,3-benzotropone (316) with cyclic α-bromo en...
Figure 15: Cycloadduct 357 and its di-π-methane rearrangement product 358.
Scheme 64: Catalytic hydrogenation of 2-chloro-4,5-benzotropone (311).
Scheme 65: Synthesis of dibromo-benzotropones from benzotropones.
Scheme 66: Bromination/dehydrobromination of benzosuberone (162).
Scheme 67: Some transformations of isomeric dibromo-benzotropones 261A/B.
Scheme 68: Transformations of benzotropolone 239B to halobenzotropolones 369–371.
Figure 16: Bromobenzotropolones 372–376 and 290 prepared via bromination/dehydrobromination strategy.
Scheme 69: Synthesis of some halobenzotropolones 289, 377 and 378.
Figure 17: Bromo-chloro-derivatives 379–381 prepared via chlorination.
Scheme 70: Synthesis of 7-iodo-3,4-benzotropolone (382).
Scheme 71: Hydrogenation of bromobenzotropolones 369 and 370.
Scheme 72: Debromination reactions of mono- and dibromides 290 and 375.
Figure 18: Nitratation and oxidation products of some halobenzotropolenes.
Scheme 73: Azo-coupling reactions of some halobenzotropolones 294, 375 and 378.
Figure 19: Four possible isomers of dibenzotropones 396–399.
Figure 20: Resonance structures of tribenzotropone (400).
Scheme 74: Two synthetic pathways for tribenzotropone (400).
Scheme 75: Synthesis of tribenzotropone (400) from dibenzotropone 399.
Scheme 76: Synthesis of tribenzotropone (400) from 9,10-phenanthraquinone (406).
Scheme 77: Synthesis of tribenzotropone (400) from trifluoromethyl-substituted arene 411.
Figure 21: Dibenzosuberone (414).
Figure 22: Reduction products 415 and 416 of tribenzotropone (400).
Figure 23: Structures of tribenzotropone dimethyl ketal 417 and 4-phenylfluorenone (412) and proposed intermed...
Figure 24: Structures of benzylidene- and methylene-9H-tribenzo[a,c,e][7]annulenes 419 and 420 and chiral phos...
Figure 25: Structures of tetracyclic alcohol 422, p-quinone methide 423 and cation 424.
Figure 26: Structures of host molecules 425–427.
Scheme 78: Synthesis of non-helical overcrowded derivatives syn/anti-431.
Figure 27: Hexabenzooctalene 432.
Figure 28: Structures of possible eight isomers 433–440 of naphthotropone.
Scheme 79: Synthesis of naphthotropone 437 starting from 1-phenylcycloheptene (441).
Scheme 80: Synthesis of 10-hydroxy-11H-cyclohepta[a]naphthalen-11-one (448) from diester 445.
Scheme 81: Synthesis of naphthotropone 433.
Scheme 82: Synthesis of naphthotropones 433 and 434 via cycloaddition reaction.
Scheme 83: Synthesis of naphthotropone 434 starting from 452.
Figure 29: Structures of tricarbonyl(tropone)irons 458, and possible cycloadducts 459.
Scheme 84: Synthesis of naphthotropone 436.
Scheme 85: Synthesis of precursor 465 for naphthotropone 435.
Scheme 86: Generation of naphthotropone 435 from 465.
Figure 30: Structures of tropylium cations 469 and 470.
Figure 31: Structures of tropylium ions 471+.BF4−, 472+.BF4−, and 473+.BF4−.
Scheme 87: Synthesis of tropylium ions 471+.BF4− and 479+.ClO4−.
Scheme 88: Synthesis of 1- and 2-methylanthracene (481 and 482) via carbene–carbene rearrangement.
Figure 32: Trapping products 488–490.
Scheme 89: Generation and chemistry of a naphthoannelated cycloheptatrienylidene-cycloheptatetraene intermedia...
Scheme 90: Proposed intermediates and reaction pathways for adduct 498.
Scheme 91: Exited-state intramolecular proton transfer of 505.
Figure 33: Benzoditropones 506 and 507.
Scheme 92: Synthesis of benzoditropone 506e.
Scheme 93: Synthetic approaches for dibenzotropone 507 via tropone (1).
Scheme 94: Formation mechanisms of benzoditropone 507 and 516 via 515.
Scheme 95: Synthesis of benzoditropones 525 and 526 from pyromellitic dianhydride (527).
Figure 34: Possible three benzocyclobutatropones 534–536.
Scheme 96: Synthesis of benzocyclobutatropones 534 and 539.
Scheme 97: Synthesis attempts for benzocyclobutatropone 545.
Scheme 98: Generation and trapping of symmetric benzocyclobutatropone 536.
Scheme 99: Synthesis of chloro-benzocyclobutatropone 552 and proposed mechanism of fluorenone derivatives.
Scheme 100: Synthesis of tropolone analogue 559.
Scheme 101: Synthesis of tropolones 561 and 562.
Figure 35: o/p-Tropoquinone rings (563 and 564) and benzotropoquinones (565–567).
Scheme 102: Synthesis of benzotropoquinone 566.
Scheme 103: Synthesis of benzotropoquinone 567 via a Diels–Alder reaction.
Figure 36: Products 575–577 through 1,2,3-benzotropoquinone hydrate 569.
Scheme 104: Structures 578–582 prepared from tropoquinone 567.
Figure 37: Two possible structures 583 and 584 for dibenzotropoquinone, and precursor compound 585 for 583.
Scheme 105: Synthesis of saddle-shaped ketone 592 using dibenzotropoquinone 584.
Beilstein J. Org. Chem. 2018, 14, 1016–1020, doi:10.3762/bjoc.14.87
Graphical Abstract
Scheme 1: Representative examples of benziodoxoles and benziodazoles.
Scheme 2: Preparation of bicyclic benziodazole 7a.
Figure 1: X-ray crystal structure of compound 7a. Ellipsoids are drawn to the 50% probability level. Selected...
Scheme 3: Benziodadiazole 7a mediated oxidatively assisted esterification and amidation reactions.
Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15
Graphical Abstract
Figure 1: Selected examples of drugs with fused pyrazole rings.
Figure 2: Typical structures of some fused pyrazoloazines from 5-aminopyrazoles.
Scheme 1: Regiospecific synthesis of 4 and 6-trifluoromethyl-1H-pyrazolo[3,4-b]pyridines.
Scheme 2: Synthesis of pyrazolo[3,4-b]pyridine-6-carboxylates.
Scheme 3: Synthesis of 1,4,6-triaryl-1H-pyrazolo[3,4-b]pyridines with ionic liquid .
Scheme 4: Synthesis of coumarin-based isomeric tetracyclic pyrazolo[3,4-b]pyridines.
Scheme 5: Synthesis of 6-substituted pyrazolo[3,4-b]pyridines under Heck conditions.
Scheme 6: Microwave-assisted palladium-catalyzed synthesis of pyrazolo[3,4-b]pyridines.
Scheme 7: Acid-catalyzed synthesis of pyrazolo[3,4-b]pyridines via enaminones.
Scheme 8: Synthesis of pyrazolo[3,4-b]pyridines via aza-Diels–Alder reaction.
Scheme 9: Synthesis of macrocyclane fused pyrazolo[3,4-b]pyridine derivatives.
Scheme 10: Three-component synthesis of 4,7-dihydro-1H-pyrazolo[3,4-b]pyridine derivatives.
Scheme 11: Ultrasonicated synthesis of spiro[indoline-3,4'-pyrazolo[3,4-b]pyridine]-2,6'(1'H)-diones.
Scheme 12: Synthesis of spiro[indoline-3,4'-pyrazolo[3,4-b]pyridine] derivatives under conventional heating co...
Scheme 13: Nanoparticle-catalyzed synthesis of pyrazolo[3,4-b]pyridine-spiroindolinones.
Scheme 14: Microwave-assisted multicomponent synthesis of spiropyrazolo[3,4-b]pyridines.
Scheme 15: Unexpected synthesis of naphthoic acid-substituted pyrazolo[3,4-b]pyridines.
Scheme 16: Multicomponent synthesis of variously substituted pyrazolo[3,4-b]pyridine derivatives.
Scheme 17: Three-component synthesis of 4,7-dihydropyrazolo[3,4-b]pyridines and pyrazolo[3,4-b]pyridines.
Scheme 18: Synthesis of pyrazolo[3,4-b]pyridine-5-spirocycloalkanediones.
Scheme 19: Ultrasound-mediated three-component synthesis of pyrazolo[3,4-b]pyridines.
Scheme 20: Multicomponent synthesis of 4-aryl-3-methyl-1-phenyl-4,6,8,9-tetrahydropyrazolo [3,4-b]thiopyrano[4...
Scheme 21: Synthesis of 2,3-dihydrochromeno[4,3-d]pyrazolo[3,4-b]pyridine-1,6-diones.
Scheme 22: FeCl3-catalyzed synthesis of o-hydroxyphenylpyrazolo[3,4-b]pyridine derivatives.
Scheme 23: Ionic liquid-mediated synthesis of pyrazolo[3,4-b]pyridines.
Scheme 24: Microwave-assisted synthesis of pyrazolo[3,4-b]pyridines.
Scheme 25: Multicomponent synthesis of pyrazolo[3,4-b]pyridine-5-carbonitriles.
Scheme 26: Unusual domino synthesis of 4,7-dihydropyrazolo[3,4-b]pyridine-5-nitriles.
Scheme 27: Synthesis of 4,5,6,7-tetrahydro-4H-pyrazolo[3,4-b]pyridines under conventional heating and ultrasou...
Scheme 28: L-Proline-catalyzed synthesis of of pyrazolo[3,4-b]pyridine.
Scheme 29: Microwave-assisted synthesis of 5-aminoarylpyrazolo[3,4-b]pyridines.
Scheme 30: Microwave-assisted multi-component synthesis of pyrazolo[3,4-e]indolizines.
Scheme 31: Synthesis of fluoropropynyl and fluoroalkyl substituted pyrazolo[1,5-a]pyrimidine.
Scheme 32: Acid-catalyzed synthesis of pyrazolo[1,5-a]pyrimidine derivatives.
Scheme 33: Chemoselective and regiospecific synthesis of 2-(3-methylpyrazol-1’-yl)-5-methylpyrazolo[1,5-a]pyri...
Scheme 34: Regioselective synthesis of 7-trifluoromethylpyrazolo[1,5-a]pyrimidines.
Scheme 35: Microwave-assisted synthesis of 7-trifluoromethylpyrazolo[1,5-a]pyrimidine carboxylates.
Scheme 36: Microwave and ultrasound-assisted synthesis of 7-trifluoromethylpyrazolo[1,5-a]pyrimidines.
Scheme 37: Base-catalyzed unprecedented synthesis of pyrazolo[1,5-a]pyrimidines via C–C bond cleavage.
Scheme 38: Synthesis of aminobenzothiazole/piperazine linked pyrazolo[1,5-a]pyrimidines.
Scheme 39: Synthesis of aminoalkylpyrazolo[1,5-a]pyrimidine-7-amines.
Scheme 40: Synthesis of pyrazolo[1,5-a]pyrimidines from condensation of 5-aminopyrazole 126 and ethyl acetoace...
Scheme 41: Synthesis of 7-aminopyrazolo[1,5-a]pyrimidines.
Scheme 42: Unexpected synthesis of 7-aminopyrazolo[1,5-a]pyrimidines under solvent free and solvent-mediated c...
Scheme 43: Synthesis of N-(4-aminophenyl)-7-aryloxypyrazolo[1,5-a]pyrimidin-5-amines.
Scheme 44: Base-catalyzed synthesis of 5,7-diarylpyrazolo[1,5-a]pyrimidines.
Scheme 45: Synthesis of 6,7-dihydropyrazolo[1,5-a]pyrimidines in PEG-400.
Scheme 46: Synthesis of 7-heteroarylpyrazolo[1,5-a]pyrimidine-3-carboxamides.
Scheme 47: Synthesis of 7-heteroarylpyrazolo[1,5-a]pyrimidine derivatives under conventional heating and micro...
Scheme 48: Synthesis of N-aroylpyrazolo[1,5-a]pyrimidine-5-amines.
Scheme 49: Regioselective synthesis of ethyl pyrazolo[1,5-a]pyrimidine-7-carboxylate.
Scheme 50: Sodium methoxide-catalyzed synthesis of 3-cyano-6,7-diarylpyrazolo[1,5-a]pyrimidines.
Scheme 51: Synthesis of various pyrazolo[3,4-d]pyrimidine derivatives.
Scheme 52: Synthesis of hydrazinopyrazolo[3,4-d]pyrimidine derivatives.
Scheme 53: Synthesis of N-arylidinepyrazolo[3,4-d]pyrimidin-5-amines.
Scheme 54: Synthesis of pyrazolo[3,4-d]pyrimidinyl-4-amines.
Scheme 55: Iodine-catalyzed synthesis of pyrazolo[3,4-d]pyrimidinones.
Scheme 56: Synthesis of ethyl 6-amino-2H-pyrazolo[3,4-d]pyrimidine-4-carboxylate.
Scheme 57: Synthesis of 4-substituted-(3,6-dihydropyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidines.
Scheme 58: Synthesis of 1-(2,4-dichlorophenyl)pyrazolo[3,4-d]pyrimidin-4-yl carboxamides.
Scheme 59: Synthesis of 5-(1,3,4-thidiazol-2-yl)pyrazolo[3,4-d]pyrimidine.
Scheme 60: One pot POCl3-catalyzed synthesis of 1-arylpyrazolo[3,4-d]pyrimidin-4-ones.
Scheme 61: Synthesis of 4-amino-N1,C3-dialkylpyrazolo[3,4-d]pyrimidines under Suzuki conditions.
Scheme 62: Microwave-assisted synthesis of pyrazolo[3,4-b]pyrazines.
Scheme 63: Synthesis and derivatization of pyrazolo[3,4-b]pyrazine-5-carbonitriles.
Scheme 64: Synthesis of 2-thioxo-pyrazolo[1,5-a][1,3,5]triazin-4-ones.
Scheme 65: Synthesis of 2,3-dihydropyrazolo[1,5-a][1,3,5]triazin-4(1H)-one.
Scheme 66: Synthesis of pyrazolo[1,5-a][1,3,5]triazine-8-carboxylic acid ethyl ester.
Scheme 67: Microwave-assisted synthesis of 4,7-dihetarylpyrazolo[1,5-a][1,3,5]triazines.
Scheme 68: Alternative synthetic route to 4,7-diheteroarylpyrazolo[1,5-a][1,3,5]triazines.
Scheme 69: Synthesis of 4-aryl-2-ethylthio-7-methylpyrazolo[1,5-a][1,3,5]triazines.
Scheme 70: Microwave-assisted synthesis of 4-aminopyrazolo[1,5-a][1,3,5]triazine.
Scheme 71: Synthesis of pyrazolo[3,4-d][1,2,3]triazines from pyrazol-5-yl diazonium salts.
Scheme 72: Synthesis of 2,5-dihydropyrazolo[3,4-e][1,2,4]triazines.
Scheme 73: Synthesis of pyrazolo[5,1-c][1,2,4]triazines via diazopyrazolylenaminones.
Scheme 74: Synthesis of pyrazolo[5,1-c][1,2,4]triazines in presence of sodium acetate.
Scheme 75: Synthesis of various 7-diazopyrazolo[5,1-c][1,2,4]triazine derivatives.
Scheme 76: One pot synthesis of pyrazolo[5,1-c][1,2,4]triazines.
Scheme 77: Synthesis of 4-amino-3,7,8-trinitropyrazolo-[5,1-c][1,2,4]triazines.
Scheme 78: Synthesis of tricyclic pyrazolo[5,1-c][1,2,4]triazines by azocoupling reaction.
Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4
Graphical Abstract
Scheme 1: General overview over the sulfur-based substrates and reactive intermediates that are discussed in ...
Scheme 2: Photoredox-catalyzed radical thiol–ene reaction, applying [Ru(bpz)3](PF6)2 as photocatalyst.
Scheme 3: Photoredox-catalyzed thiol–ene reaction of aliphatic thiols with alkenes enabled by aniline derivat...
Scheme 4: Photoredox-catalyzed radical thiol–ene reaction for the postfunctionalization of polymers (a) and n...
Scheme 5: Photoredox-catalyzed thiol–ene reaction enabled by bromotrichloromethane as redox additive.
Scheme 6: Photoredox-catalyzed preparation of β-ketosulfoxides with Eosin Y as organic dye as photoredox cata...
Scheme 7: Greaney’s photocatalytic radical thiol–ene reaction, applying TiO2 nanoparticles as photocatalyst.
Scheme 8: Fadeyi’s photocatalytic radical thiol–ene reaction, applying Bi2O3 as photocatalyst.
Scheme 9: Ananikov’s photocatalytic radical thiol-yne reaction, applying Eosin Y as photocatalyst.
Scheme 10: Organocatalytic visible-light photoinitiated thiol–ene coupling, applying phenylglyoxylic acid as o...
Scheme 11: Xia’s photoredox-catalyzed synthesis of 2,3-disubstituted benzothiophenes, applying 9-mesityl-10-me...
Scheme 12: Wang’s metal-free photoredox-catalyzed radical thiol–ene reaction, applying 9-mesityl-10-methylacri...
Scheme 13: Visible-light benzophenone-catalyzed metal- and oxidant-free radical thiol–ene reaction.
Scheme 14: Visible-light catalyzed C-3 sulfenylation of indole derivatives using Rose Bengal as organic dye.
Scheme 15: Photocatalyzed radical thiol–ene reaction and subsequent aerobic sulfide-oxidation with Rose Bengal...
Scheme 16: Photoredox-catalyzed synthesis of diaryl sulfides.
Scheme 17: Photocatalytic cross-coupling of aryl thiols with aryl diazonium salts, using Eosin Y as photoredox...
Scheme 18: Photocatalyzed cross-coupling of aryl diazonium salts with cysteines in batch and in a microphotore...
Scheme 19: Fu’s [Ir]-catalyzed photoredox arylation of aryl thiols with aryl halides.
Scheme 20: Fu’s photoredox-catalyzed difluoromethylation of aryl thiols.
Scheme 21: C–S cross-coupling of thiols with aryl iodides via [Ir]-photoredox and [Ni]-dual-catalysis.
Scheme 22: C–S cross-coupling of thiols with aryl bromides, applying 3,7-bis-(biphenyl-4-yl)-10-(1-naphthyl)ph...
Scheme 23: Collin’s photochemical dual-catalytic cross-coupling of thiols with bromoalkynes.
Scheme 24: Visible-light-promoted C–S cross-coupling via intermolecular electron donor–acceptor complex format...
Scheme 25: Li’s visible-light photoredox-catalyzed thiocyanation of indole derivatives with Rose Bengal as pho...
Scheme 26: Hajra’s visible-light photoredox-catalyzed thiocyanation of imidazoheterocycles with Eosin Y as pho...
Scheme 27: Wang’s photoredox-catalyzed thiocyanation reaction of indoles, applying heterogeneous TiO2/MoS2 nan...
Scheme 28: Yadav’s photoredox-catalyzed α-C(sp3)–H thiocyanation reaction for tertiary amines, applying Eosin ...
Scheme 29: Yadav’s photoredox-catalyzed synthesis of 5-aryl-2-imino-1,3-oxathiolanes.
Scheme 30: Yadav’s photoredox-catalyzed synthesis of 1,3-oxathiolane-2-thiones.
Scheme 31: Li’s photoredox catalysis for the preparation of 2-substituted benzothiazoles, applying [Ru(bpy)3](...
Scheme 32: Lei’s external oxidant-free synthesis of 2-substituted benzothiazoles by merging photoredox and tra...
Scheme 33: Metal-free photocatalyzed synthesis of 2-aminobenzothiazoles, applying Eosin Y as photocatalyst.
Scheme 34: Metal-free photocatalyzed synthesis of 1,3,4-thiadiazoles, using Eosin Y as photocatalyst.
Scheme 35: Visible-light photoredox-catalyzed preparation of benzothiophenes with Eosin Y.
Scheme 36: Visible-light-induced KOH/DMSO superbase-promoted preparation of benzothiophenes.
Scheme 37: Jacobi von Wangelin’s photocatalytic approach for the synthesis of aryl sulfides, applying Eosin Y ...
Scheme 38: Visible-light photosensitized α-C(sp3)–H thiolation of aliphatic ethers.
Scheme 39: Visible-light photocatalyzed cross-coupling of alkyl and aryl thiosulfates with aryl diazonium salt...
Scheme 40: Visible-light photocatalyzed, controllable sulfenylation and sulfoxidation with organic thiosulfate...
Scheme 41: Rastogi’s photoredox-catalyzed methylsulfoxidation of aryl diazonium salts, using [Ru(bpy)3]Cl2 as ...
Scheme 42: a) Visible-light metal-free Eosin Y-catalyzed procedure for the preparation of vinyl sulfones from ...
Scheme 43: Visible-light photocatalyzed cross-coupling of sodium sulfinates with secondary enamides.
Scheme 44: Wang’s photocatalyzed oxidative cyclization of phenyl propiolates with sulfinic acids, applying Eos...
Scheme 45: Lei’s sacrificial oxidant-free synthesis of allyl sulfones by merging photoredox and transition met...
Scheme 46: Photocatalyzed Markovnikov-selective radical/radical cross-coupling of aryl sulfinic acids and term...
Scheme 47: Visible-light Eosin Y induced cross-coupling of aryl sulfinic acids and styrene derivatives, afford...
Scheme 48: Photoredox-catalyzed bicyclization of 1,7-enynes with sulfinic acids, applying Eosin Y as photocata...
Scheme 49: Visible-light-accelerated C–H-sulfinylation of arenes and heteroarenes.
Scheme 50: Visible-light photoredox-catalyzed β-selenosulfonylation of electron-rich olefins, applying [Ru(bpy)...
Scheme 51: Photocatalyzed preparation of β-chlorosulfones from the respective olefins and p-toluenesulfonyl ch...
Scheme 52: a) Photocatalyzed preparation of β-amidovinyl sulfones from sulfonyl chlorides. b) Preparation of β...
Scheme 53: Visible-light photocatalyzed sulfonylation of aliphatic tertiary amines, applying [Ru(bpy)3](PF6)2 ...
Scheme 54: Reiser’s visible-light photoredox-catalyzed preparation of β-hydroxysulfones from sulfonyl chloride...
Scheme 55: a) Sun’s visible-light-catalyzed approach for the preparation of isoquinolinonediones, applying [fac...
Scheme 56: Visible-light photocatalyzed sulfonylation/cyclization of vinyl azides, applying [Ru(bpy)3]Cl2 as p...
Scheme 57: Visible-light photocatalyzed procedure for the formation of β-ketosulfones from aryl sulfonyl chlor...
Scheme 58: Zheng’s method for the sulfenylation of indole derivatives, applying sulfonyl chlorides via visible...
Scheme 59: Cai’s visible-light induced synthesis of β-ketosulfones from sulfonyl hydrazines and alkynes.
Scheme 60: Photoredox-catalyzed approach for the preparation of vinyl sulfones from sulfonyl hydrazines and ci...
Scheme 61: Jacobi von Wangelin’s visible-light photocatalyzed chlorosulfonylation of anilines.
Scheme 62: Three-component photoredox-catalyzed synthesis of N-amino sulfonamides, applying PDI as organic dye....
Scheme 63: Visible-light induced preparation of complex sulfones from oximes, silyl enol ethers and SO2.
Beilstein J. Org. Chem. 2017, 13, 2442–2457, doi:10.3762/bjoc.13.241
Graphical Abstract
Figure 1: A. Dependence of the lipophilicity (logP) on the number of fluorine atoms in a partially fluorinate...
Scheme 1: Synthesis of the model compounds.
Figure 2: Kinetics of the C-terminal ester hydrolysis.
Figure 3: Partitioning of the esters 1–5 between octan-1-ol and water. Insert: comparison with the other part...
Scheme 2: Amide isomerism in the N-acetylprolyl fragment.
Figure 4: Enhancement of the trans/cis thermodynamic preferences in the ester models as a function of the sol...
Scheme 3: A. Four-state conformational equilibrium model used by Siebler et al. [72] for explanations of the elev...
Scheme 4: Elevation of the trans/cis ratio in derivatives of N-acyl proline may result from the enhanced n→π*...
Scheme 5: Synthesis of the model peptides.
Figure 5: Mean residue molar circular dichroism (Δε) of peptides 8–10 in methanol (left) and aqueous phosphat...
Figure 6: Conformational analysis of the peptides by 1H DOSY NMR (D2O, 298 K). The theoretical values were ca...
Figure 7: Hydrolysis of the C-terminal 2,2-difluoroethyl esters of the oligopeptides in buffered deuterium ox...
Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201
Graphical Abstract
Scheme 1: The mechanistic outline of the intermolecular (a) and intramolecular (b) glycosylation reactions.
Figure 1: Three general concepts for intramolecular glycosylation reactions.
Scheme 2: First intramolecular glycosylation using the molecular clamping.
Scheme 3: Succinoyl as a flexible linker for intramolecular glycosylation of prearranged glycosides.
Scheme 4: Template-directed cyclo-glycosylation using a phthaloyl linker.
Scheme 5: Phthaloyl linker-mediated synthesis of branched oligosaccharides via remote glycosidation.
Scheme 6: Molecular clamping with the phthaloyl linker in the synthesis of α-cyclodextrin.
Scheme 7: m-Xylylene as a rigid tether for intramolecular glycosylation.
Scheme 8: Oligosaccharide synthesis using rigid xylylene linkers.
Scheme 9: Stereo- and regiochemical outcome of peptide-based linkers.
Scheme 10: Positioning effect of donor and acceptor in peptide templated synthesis.
Scheme 11: Synthesis of a trisaccharide using a non-symmetrical tether strategy.
Scheme 12: Effect of ring on glycosylation with a furanose.
Scheme 13: Rigid BPA template with various linkers.
Scheme 14: The templated synthesis of maltotriose in complete stereoselectivity.
Scheme 15: First examples of the IAD.
Scheme 16: Long range IAD via dimethylsilane.
Scheme 17: Allyl-mediated tethering strategy in the IAD.
Scheme 18: IAD using tethering via the 2-naphthylmethyl group.
Scheme 19: Origin of selectivity in boronic ester mediated IAD.
Scheme 20: Arylborinic acid approach to the synthesis of β-mannosides.
Figure 2: Facial selectivity during HAD.
Scheme 21: Possible mechanisms to explain α and β selectivity in palladium mediated IAD.
Scheme 22: DISAL as the leaving group that favors the intramolecular glycosylation pathway.
Scheme 23: Boronic acid as a directing group in the leaving group-based glycosylation method.
Beilstein J. Org. Chem. 2017, 13, 1564–1571, doi:10.3762/bjoc.13.156
Graphical Abstract
Figure 1: Prominent oxoaporphine and oxoisoaporphine alkaloids: liriodenine (1), menisporphine (2), dauriporp...
Scheme 1: Previously reported [7,17] and new approach to oxoisoaporphine alkaloids.
Scheme 2: Synthesis of iodinated isoquinolines 8a–c from alkoxy-substituted isoquinolines 7a–c.
Scheme 3: Synthesis of methyl 2-(isoquinolin-1-yl)benzoates 10a–c from 1-iodoisoquinolines 8a–c.
Scheme 4: Synthesis of the alkaloids 6-O-demethylmenisporphine (4), dauriporphinoline (5), and bianfugecine (6...
Scheme 5: Attempted synthesis of bianfugecine (6) via directed remote metalation and subsequent trapping of t...
Scheme 6: Outcome of a D2O quenching experiment after metalation of amide 12.
Scheme 7: Synthesis of 1-arylnaphthalene analogues 15 and 16.
Scheme 8: Outcome of a D2O quenching experiment after metalation of amide 16 with LDA.
Scheme 9: Synthesis of the alkaloids menisporphine (2) and dauriporphine (3) by O-methylation of the alkaloid...
Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128
Graphical Abstract
Figure 1: Chemical structures of the basic compounds used in this study.
Scheme 1: Synthesis of the BODIPY building block (part A) and construct 6 (part B).
Figure 2: Absorbance and fluorescence spectra of compounds 3–6. UV spectra (part A) were recorded with a conc...
Figure 3: NO production in primary rat macrophages. The cells were treated with Tb, compounds 4, 5, and Tb-co...
Figure 4: Atomic force microscopy images of liposomes, 5 µm area: A) 2D image, B) 3D image (Ra = 2.4 nm); 2 µ...
Figure 5: Panel of images from live-cell fluorescence microscopy: intracellular localization of construct 6 i...
Figure 6: Panel of images from live-cell fluorescence microscopy: intracellular localization of liposomes wit...
Beilstein J. Org. Chem. 2017, 13, 863–873, doi:10.3762/bjoc.13.87
Graphical Abstract
Scheme 1: Synthetic route towards monomers M1, M2 and M3.
Scheme 2: Synthesis of polymers P1, P2, and P3.
Figure 1: Isodensity surface plots of frontier molecular orbitals and optimized molecular geometries of P1, P2...
Figure 2: Theoretical absorption spectra of the polymers P1–P3 calculated using TDDFT.
Figure 3: Electrochemical spectra of polymers P1–P3.
Figure 4: Normalized absorption spectra of the polymers in solution, film and annealed film (130 °C) forms.
Figure 5: Photoluminescence spectra of polymers P1–P3 and polymer:PC70BM blends.
Figure 6: Bulk heterojunction solar cells device architecture, illustrating favorable conditions for absorpti...
Figure 7: J–V Spectra in chlorobenzene (CB) for which the ratio of polymer:PC70BM was optimized as follows: P1...
Figure 8: External quantum efficiency spectra of optimized devices fabricated with polymers P1, P2 and P3 and...
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 (...
Beilstein J. Org. Chem. 2017, 13, 33–42, doi:10.3762/bjoc.13.5
Graphical Abstract
Figure 1: Menthol auxiliaries 1–4 used in the following anodic coupling reactions.
Scheme 1: Synthesis of carboxylic acids 13a/b–18a/b.
Scheme 2: (a) Preparation of benzyl 2-isopropylmalonate (5) and (b) preparation of benzyl 2-tert-butylmalonat...
Scheme 3: Coelectrolysis (hetero-coupling) of carboxylic acids 13–17 with 3,3-dimethylbutyric acid (20).
Figure 2: Crystal structure of the minor diastereomer 23b.
Figure 3: Cyclic voltammograms of the malonic derivatives 15a/b, 16a/b and 18a/b (scan rate: 500 mA/s, solven...
Scheme 4: Homo-coupling of carboxylic acids 13a/b–16a/b to diesters 26a/b/c–29a/b/c (n.d.: not determined).
Figure 4: Crystal structure of major diastereomer 28a.
Figure 5: Crystal structure of major diastereomer 29a.
Figure 6: Discrimination of diastereomeric faces in the menthol substituted radical A and in the 8-phenylment...
Scheme 5: Reductive cleavage of 30a–c to 8-phenylmenthol (3) and 31a–c.
Beilstein J. Org. Chem. 2016, 12, 2267–2273, doi:10.3762/bjoc.12.219
Graphical Abstract
Figure 1: Steric repulsion between ortho-hydrogen atoms in benzene-1,3,5-tribenzoic acid (BTB) leads to a non...
Figure 2: Mono-substituted TATB linkers 1b–d were successfully employed in the isoreticular syntheses of PCN-...
Figure 3: Retrosynthetic analysis for extended TATBs 2: triple Suzuki coupling between tribromotriazines 3 an...
Figure 4: Synthesis of unsymmetrically substituted 2,4,6-tris(bromoaryl)-1,3,5-triazines 3 from one equivalen...
Figure 5: Synthesis of 4-bromo-3-nitrobenzoyl chloride (5b). Conditions: a) HNO3/H2SO4, 3 h 0 °C, 2 h, room t...
Figure 6: Syntheses of 4-bromo-3-methoxybenzoyl chloride (5c). Conditions: a) Br2, EtOH/HOAc, 30 min, room te...
Figure 7: Triple Suzuki–Miyaura coupling between tribromotriazines 3 and boronic acid 15 and subsequent hydro...
Figure 8: Triple Suzuki coupling between tribromotriazines 3 and boronate 18. Conditions: a) 19a: Pd(PPh3)4, K...
Beilstein J. Org. Chem. 2016, 12, 1170–1177, doi:10.3762/bjoc.12.112
Graphical Abstract
Scheme 1: Synthesis of highly functionalized 2,2'-bipyridines 4a and 5b from symmetrical 1,3-diketones 1a and ...
Scheme 2: Synthesis of β-ketoenamines 2c–e and of β-ketoenamides 3c–h.
Scheme 3: Synthesis of α-methoxy-β-ketoenamine 2i, its N-acylation to 3i and the reaction of β-ketoenamide 3a...
Scheme 4: Cyclizations of β-ketoenamide 3i leading to 2,2´-bipyridine derivative 4i or to the related 2-(2-py...
Scheme 5: Suzuki-couplings of 2,2'-bipyrid-4-yl nonaflates 5a and 5b to compounds 9 and 10.
Scheme 6: Palladium-catalyzed couplings of chloro-substituted 2,2'-bipyrid-4-yl nonaflate 5g leading to compo...
Beilstein J. Org. Chem. 2016, 12, 1136–1152, doi:10.3762/bjoc.12.110
Graphical Abstract
Scheme 1: Divergent behavior of the palladium and ruthenium-catalyzed Alder–ene reaction.
Scheme 2: Some asymmetric enyne cycloisomerization reactions.
Figure 1: (a) Mechanism for the redox biscycloisomerization reaction. (b) Ruthenium catalyst containing a tet...
Scheme 3: Synthesis of p-anisyl catalyst 1.
Figure 2: Failed sulfinate ester syntheses.
Scheme 4: Using norephedrine-based oxathiazolidine-2-oxide 7 for chiral sulfoxide synthesis.
Scheme 5: (a) General synthetic sequence to access enyne bicycloisomerization substrates (b) Synthesis of 2-c...
Figure 3: Failed bicycloisomerization substrates. Reactions performed at 40 °C for 16 hours with 3 mol % of c...
Scheme 6: Deprotection of [3.1.0] bicycles and X-ray crystal structure of 76.
Scheme 7: ProPhenol-catalyzed addition of zinc acetylide to acetaldehyde for the synthesis of a chiral 1,6-en...
Figure 4: Diastereomeric metal complexes formed after alcohol coordination.
Scheme 8: Curtin–Hammitt scenario of redox bicycloisomerization in acetone.
Beilstein J. Org. Chem. 2016, 12, 1127–1135, doi:10.3762/bjoc.12.109
Graphical Abstract
Figure 1: Structure of squalenic acid-d6, gemcitabine and GemSQ-d6 conjugate.
Scheme 1: Retrosynthetic route to SQCO2H-d6 (1) and synthetic routes for the preparation of dialdehyde 5 and ...
Scheme 2: Implementation of the deuterated isopropylidene end-group by the Shapiro reaction of trisylhydrazon...
Scheme 3: Attempted synthesis of 1 via the protection of the aldehyde 10 as a 5,5-dimethyl-1,3-dioxane.
Scheme 4: Synthesis of squalenic acid-d6 1 and conjugation to gemcitabine.
Figure 2: A) Sketch depicting the procedure of preparing the NAs. B) Single Raman spectra of GemSQ-d6 NAs, Ge...
Beilstein J. Org. Chem. 2016, 12, 963–968, doi:10.3762/bjoc.12.95
Graphical Abstract
Figure 1: Chemical structures of N-pentylpantothenamide (1) and of its methyl allyl derivative 2.
Figure 2: Structure of Grubbs’ catalysts used in this study.
Scheme 1: From (R)-malic acid to allyl derivatives 8 and 9 tested in cross-metathesis. Details are provided i...
Scheme 2: Synthesis of compounds 10c and 10d.
Scheme 3: Synthesis of 16.
Figure 3: In vitro antiplasmodial activity of compound 16 in growth medium containing pantetheinase (open sym...
Beilstein J. Org. Chem. 2015, 11, 1886–1892, doi:10.3762/bjoc.11.203
Graphical Abstract
Figure 1: Catalysts 1–4 tested for the metathesis of profluorescent substrates.
Scheme 1: Two profluorescent substrates yielding fluorescent products upon ring-closing metathesis.
Scheme 2: Synthesis of the two profluorescent substrates amenable to ring-closing metathesis.
Figure 2: Fluorescence evolution resulting from closing metathesis of umbelliferone precursor 8 (λexcitation ...
Figure 3: Fluorescence evolution resulting from closing metathesis of fluorescence–quencher substrate 5 (λexc...
Figure 4: Comparison of kinetics measured by HPLC a) and by a plate reader b) for the ring-closing metathesis...
Beilstein J. Org. Chem. 2015, 11, 437–445, doi:10.3762/bjoc.11.50
Graphical Abstract
Figure 1: A selection of highly substituted/functionalized [2.2]paracyclophanes.
Figure 2: A selection of [2.2]paracyclophanes carrying several nitrogen-containing substituents.
Scheme 1: The preparation of 4,12-diamino[2.2]paracyclophane (8).
Scheme 2: Preparation of cyclic and acyclic urethanes from 4,12-diisocyanato[2.2]paracyclophane (16).
Figure 3: (a, above): The molecule of compound 18 in the crystal; ellipsoids represent 50% probability levels...
Scheme 3: LiAlH4-reduction of crownophane 18.
Figure 4: (a, above): The molecule of compound 22 in the crystal; ellipsoids represent 30% probability levels...
Scheme 4: The preparation of several derivatives of 4,16-dicarboxy[2.2]paracyclophane (25) carrying N-contain...
Figure 5: The molecule of compound 26 in the crystal; ellipsoids represent 50% probability levels. Only the a...
Figure 6: (a, above): The molecule of compound 28 in the crystal; ellipsoids represent 50% probability levels...
Beilstein J. Org. Chem. 2014, 10, 2566–2572, doi:10.3762/bjoc.10.268
Graphical Abstract
Figure 1: Amino acid functionalized nucleosides.
Scheme 1: Reagents and conditions: a) i. Et3N, Pd(PPh3)4, THF, CO (4 bar), 70 °C, 48 h, ii. Et3N, di-tert-but...
Scheme 2: Reagents and conditions: a) Et3N, Pd(PPh3)4, THF, CO (4 bar), 48 h, 70 °C (68%); b) Et3N·3HF, Et3N,...
Scheme 3: Reagents and conditions: a) Et3N, Pd(PPh3)4, THF, CO (4 bar), 48 h, 70 °C (90%); b) Et3N·3HF, Et3N,...