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Search for "N-sulfonyl" in Full Text gives 35 result(s) in Beilstein Journal of Organic Chemistry.
Synthesis of 1-indanones with a broad range of biological activity
- Marika Turek,
- Dorota Szczęsna,
- Marek Koprowski and
- Piotr Bałczewski
Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48
- of palladium catalyst and gaseous oxygen as the terminal oxidant (Scheme 65). 1.8 From other compounds In 2016, Shi et al. have developed an unique, conditions-controlled [Rh2(esp)2] (esp = α,α,α’,α’-tetramethyl-1,3-benzenedipropionic acid)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles 235 leading
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 (...
Cupreines and cupreidines: an established class of bifunctional cinchona organocatalysts
- Laura A. Bryant,
- Rossana Fanelli and
- Alexander J. A. Cobb
Beilstein J. Org. Chem. 2016, 12, 429–443, doi:10.3762/bjoc.12.46
- developed an aza-MBH process using β-ICPD in the reaction between N-sulfonyl-1-aza-1,3-butadienes and activated alkenes (Scheme 4) [25]. In this report, optimal selectivity required (R)-BINOL as a co-catalyst (see inset for proposed catalytic transition state – (R)-BINOL shown in red). Furthermore, the
Graphical Abstract
Figure 1: The structural diversity of the cinchona alkaloids, along with cupreine, cupreidine, β-isoquinidine...
Scheme 1: The original 6’-OH cinchona alkaloid organocatalytic MBH process, showing how the free 6’-OH is ess...
Scheme 2: Use of β-ICPD in an aza-MBH reaction.
Scheme 3: (a) The isatin motif is a common feature for MBH processes catalyzed by β-ICPD, as demonstrated by ...
Scheme 4: (a) Chen’s asymmetric MBH reaction. Good selectivity was dependent upon the presence of (R)-BINOL (...
Scheme 5: Lu and co-workers synthesis of a spiroxindole.
Scheme 6: Kesavan and co-workers’ synthesis of spiroxindoles.
Scheme 7: Frontier’s Nazarov cyclization catalyzed by β-ICPD.
Scheme 8: The first asymmetric nitroaldol process catalyzed by a 6’-OH cinchona alkaloid.
Scheme 9: A cupreidine derived catalyst induces a dynamic kinetic asymmetric transformation.
Scheme 10: Cupreine derivative 38 has been used in an organocatalytic asymmetric Friedel–Crafts reaction.
Scheme 11: Examples of 6’-OH cinchona alkaloid catalyzed processes include: (a) Deng’s addition of dimethyl ma...
Scheme 12: A diastereodivergent sulfa-Michael addition developed by Melchiorre and co-workers.
Scheme 13: Melchiorre’s vinylogous Michael addition.
Scheme 14: Simpkins’s TKP conjugate addition reactions.
Scheme 15: Hydrocupreine catalyst HCPN-59 can be used in an asymmetric cyclopropanation.
Scheme 16: The hydrocupreine and hydrocupreidine-based catalysts HCPN-65 and HCPD-67 demonstrate the potential...
Scheme 17: Jørgensen’s oxaziridination.
Scheme 18: Zhou’s α-amination using β-ICPD.
Scheme 19: Meng’s cupreidine catalyzed α-hydroxylation.
Scheme 20: Shi’s biomimetic transamination process for the synthesis of α-amino acids.
Scheme 21: β-Isocupreidine catalyzed [4 + 2] cycloadditions.
Scheme 22: β-Isocupreidine catalyzed [2+2] cycloaddition.
Scheme 23: A domino reaction catalyst by cupreidine catalyst CPD-30.
Scheme 24: (a) Dixon’s 6’-OH cinchona alkaloid catalyzed oxidative coupling. (b) An asymmetric oxidative coupl...
Fates of imine intermediates in radical cyclizations of N-sulfonylindoles and ene-sulfonamides
- Hanmo Zhang,
- E. Ben Hay,
- Stephen J. Geib and
- Dennis P. Curran
Beilstein J. Org. Chem. 2015, 11, 1649–1655, doi:10.3762/bjoc.11.181
- /fragmentation. Tin hydride-mediated cyclizations of 2-halo-N-(3-methyl-N-sulfonylindole)anilines provide spiro[indoline-3,3'-indolones] or spiro-3,3'-biindolines (derived from imine reduction), depending on the indole C2 substituent. Cyclizations of 2-haloanilide derivatives of 3-carboxy-N-sulfonyl-2,3
- alkaloid aspidophytine published in 2008 [14]. In 2005, Stevens and coworkers reported that treatment of trichloroacetamide-substituted N-sulfonylindole 3 under conditions for copper-catalyzed atom transfer cyclization provided chlorine transfer product 4 with the N-sulfonyl group intact (Scheme 1) [15
Graphical Abstract
Figure 1: (a) Radical reactions of ene-sulfonamides give diverse isolated products; (b) these products are of...
Figure 2: Isolation of stable imines strengthens the case for sulfonyl radical elimination.
Scheme 1: Cyclizations of N-sulfonylindole 3 occur with retention or elimination of the sulfonyl group depend...
Scheme 2: Aryl radical cyclization to N-sulfonylindoles.
Figure 3: Mechanistic aspects of cyclizations shown in Scheme 2; (a) mechanism for formation of 7; (b) possible reaso...
Figure 4: Substrate design by swapping radical precursor and acceptor.
Scheme 3: Synthesis and cyclization of precursors 22–24.
Figure 5: ORTEP representation of the crystal structure of 27.
Figure 6: Proposed hydration/retro-Claisen path to formamides.
Chiral phosphines in nucleophilic organocatalysis
- Yumei Xiao,
- Zhanhu Sun,
- Hongchao Guo and
- Ohyun Kwon
Beilstein J. Org. Chem. 2014, 10, 2089–2121, doi:10.3762/bjoc.10.218
- H14, Zhong and Loh developed asymmetric [4 + 2] annulations of activated N-sulfonyl-1-aza-1,3-dienes and alkenes through tandem RC/Michael reactions (Scheme 51) [94]. In the presence of 10 mol % of H14, various 1-aza-1,3-dienes smoothly underwent [4 + 2] annulations with enones in chloroform at room
- temperature, affording a broad spectrum of densely functionalized tetrahydropyridine derivatives, with exclusive 4,5-trans diastereoselectivity, excellent enantioselectivity, and good to excellent yields. The transformations tolerated a wide range of N-sulfonyl-1-aza-1,3-dienes with different C4-substituents
Graphical Abstract
Figure 1: Cyclic chiral phosphines based on bridged-ring skeletons.
Figure 2: Cyclic chiral phosphines based on binaphthyl skeletons.
Figure 3: Cyclic chiral phosphines based on ferrocene skeletons.
Figure 4: Cyclic chiral phosphines based on spirocyclic skeletons.
Figure 5: Cyclic chiral phosphines based on phospholane ring skeletons.
Figure 6: Acyclic chiral phosphines.
Figure 7: Multifunctional chiral phosphines based on binaphthyl skeletons.
Figure 8: Multifunctional chiral phosphines based on amino acid skeletons.
Scheme 1: Asymmetric [3 + 2] annulations of allenoates with electron-deficient olefins, catalyzed by the chir...
Scheme 2: Asymmetric [3 + 2] annulations of allenoate and enones, catalyzed by the chiral binaphthyl-based ph...
Scheme 3: Asymmetric [3 + 2] annulations of N-substituted olefins and allenoates, catalyzed by the chiral bin...
Scheme 4: Asymmetric [3 + 2] annulations of 2-aryl-1,1-dicyanoethylenes with ethyl allenoate, catalyzed by th...
Scheme 5: Asymmetric [3 + 2] annulations of 3-alkylideneindolin-2-ones with ethyl allenoate, catalyzed by the...
Scheme 6: Asymmetric [3 + 2] annulations of 2,6-diarylidenecyclohexanones with allenoates, catalyzed by the c...
Scheme 7: Asymmetric [3 + 2] annulations of allenoate with alkylidene azlactones, catalyzed by the chiral bin...
Scheme 8: Asymmetric [3 + 2] annulations of C60 with allenoates, catalyzed by the chiral phosphine B6.
Scheme 9: Asymmetric [3 + 2] annulations of α,β-unsaturated esters and ketones with an allenoate, catalyzed b...
Scheme 10: Asymmetric [3 + 2] annulations of exocyclic enones with allenoates, catalyzed by the ferrocene-modi...
Scheme 11: Asymmetric [3 + 2] annulations of enones with an allenylphosphonate, catalyzed by the ferrocene-mod...
Scheme 12: Asymmetric [3 + 2] annulations of 3-alkylidene-oxindoles with ethyl allenoate, catalyzed by the fer...
Scheme 13: Asymmetric [3 + 2] annulations of dibenzylideneacetones with ethyl allenoate, catalyzed by the ferr...
Scheme 14: Asymmetric [3 + 2] annulations of trisubstituted alkenes with ethyl allenoate, catalyzed by the fer...
Scheme 15: Asymmetric [3 + 2] annulations of 2,6-diarylidenecyclohexanones with allenoates, catalyzed by the f...
Scheme 16: Asymmetric [3 + 2] annulations of α,β-unsaturated ketones with ethyl allenoates, catalyzed by the f...
Scheme 17: Asymmetric [3 + 2] annulations of α,β-unsaturated esters with allenoates, catalyzed by the ferrocen...
Scheme 18: Asymmetric [3 + 2] annulations of alkylidene azlactones with allenoates, catalyzed by the chiral sp...
Scheme 19: Asymmetric [3 + 2] annulations of α-trimethylsilyl allenones and electron-deficient olefins, cataly...
Scheme 20: Asymmetric [3 + 2] annulations of α,β-unsaturated ketones with an allenone, catalyzed by the chiral...
Scheme 21: Asymmetric [3 + 2] annulations of cyclic enones with allenoates, catalyzed by the chiral α-amino ac...
Scheme 22: Asymmetric [3 + 2] annulations of arylidenemalononitriles and analogues with an allenoate, catalyze...
Scheme 23: Asymmetric [3 + 2] annulations of α,β-unsaturated esters with an allenoate, catalyzed by the chiral...
Scheme 24: Asymmetric [3 + 2] annulations of 3,5-dimethyl-1H-pyrazole-derived acrylamides with an allenoate, c...
Scheme 25: Asymmetric [3 + 2] annulations of maleimides with allenoates, catalyzed by the chiral phosphine H10....
Scheme 26: Asymmetric [3 + 2] annulations of α-substituted acrylates with allenoate, catalyzed by the chiral p...
Scheme 27: Asymmetric [3 + 2] annulation of an N-tosylimine with an allenoate, catalyzed by the chiral phosphi...
Scheme 28: Asymmetric [3 + 2] annulations of N-tosylimines with an allenoate, catalyzed by the chiral phosphin...
Scheme 29: Asymmetric [3 + 2] annulations of N-tosylimines with an allenoate, catalyzed by the chiral phosphin...
Scheme 30: Asymmetric [3 + 2] annulations of N-diphenylphosphinoyl aromatic imines with butynoates, catalyzed ...
Scheme 31: Asymmetric [3 + 2] annulations of N-tosylimines with allenylphosphonates, catalyzed by the chiral p...
Scheme 32: Asymmetric [3 + 2] annulation of an N-tosylimine with an allenoate, catalyzed by the chiral phosphi...
Scheme 33: Asymmetric [3 + 2] annulations of N-diphenylphosphinoyl aromatic imines with allenoates (top), cata...
Scheme 34: Asymmetric [3 + 2] annulation of N-diphenylphosphinoylimines with allenoates, catalyzed by the chir...
Scheme 35: Asymmetric [3 + 2] annulation of an azomethine imine with an allenoate, catalyzed by the chiral pho...
Scheme 36: Asymmetric [3 + 2] annulations between α,β-unsaturated esters/ketones and 3-butynoates, catalyzed b...
Scheme 37: Asymmetric intramolecular [3 + 2] annulations of electron-deficient alkenes and MBH carbonates, cat...
Scheme 38: Asymmetric [3 + 2] annulations of methyleneindolinone and methylenebenzofuranone derivatives with M...
Scheme 39: Asymmetric [3 + 2] annulations of activated isatin-based alkenes with MBH carbonates, catalyzed by ...
Scheme 40: Asymmetric [3 + 2] annulations of maleimides with MBH carbonates, catalyzed by the chiral phosphine ...
Scheme 41: A series of [3 + 2] annulations of various activated alkenes with MBH carbonates, catalyzed by the ...
Scheme 42: Asymmetric [3 + 2] annulations of an alkyne with isatins, catalyzed by the chiral phosphine F1.
Scheme 43: Asymmetric [4 + 2] annulations catalyzed by the chiral phosphine B1.
Scheme 44: Asymmetric [4 + 2] annulations catalyzed by the chiral phosphine H5.
Scheme 45: Asymmetric [4 + 2] annulations catalyzed by the chiral phosphines H13 and H12.
Scheme 46: Asymmetric [4 + 2] annulations catalyzed by the chiral phosphine H6.
Scheme 47: Kerrigan’s [2 + 2] annulations of ketenes with imines, catalyzed by the chiral phosphine B7.
Scheme 48: Asymmetric [4 + 1] annulations, catalyzed by the chiral phosphine G6.
Scheme 49: Asymmetric homodimerization of ketenes, catalyzed by the chiral phosphine F5 and F6.
Scheme 50: Aza-MBH/Michael reactions, catalyzed by the chiral phosphine G1.
Scheme 51: Tandem RC/Michael additions, catalyzed by the chiral phosphine H14.
Scheme 52: Intramolecular tandem RC/Michael addition, catalyzed by the chiral phosphine H15.
Scheme 53: Double-Michael addition, catalyzed by the chiral aminophosphine G9.
Scheme 54: Tandem Michael addition/Wittig olefinations, mediated by the chiral phosphine BIPHEP.
Scheme 55: Asymmetric Michael additions, catalyzed by the chiral phosphines H7, H8, and H9.
Scheme 56: Asymmetric γ-umpolung additions, catalyzed by the chiral phosphine A1.
Scheme 57: Asymmetric γ-umpolung additions, catalyzed by the chiral phosphines E2 and E3.
Scheme 58: Intramolecular γ-additions of hydroxy-2-alkynoates, catalyzed by the chiral phosphine D2.
Scheme 59: Intra-/intermolecular γ-additions, catalyzed by the chiral phosphine D2.
Scheme 60: Intermolecular γ-additions, catalyzed by the chiral phosphines B5 and B3.
Scheme 61: Intermolecular γ-additions, catalyzed by the chiral phosphines E6 and B4.
Scheme 62: Asymmetric allylic substitution of MBH acetates, catalyzed by the chiral phosphine G2.
Scheme 63: Allylic substitutions between MBH acetates or carbonates and an array of nucleophiles, catalyzed by...
Scheme 64: Asymmetric acylation of diols, catalyzed by the chiral phosphines E4 and E5.
Scheme 65: Kinetic resolution of secondary alcohols, catalyzed by the chiral phosphine E8 and E9.
One-pot three-component synthesis and photophysical characteristics of novel triene merocyanines
- Christian Muschelknautz,
- Robin Visse,
- Jan Nordmann and
- Thomas J. J. Müller
Beilstein J. Org. Chem. 2014, 10, 599–612, doi:10.3762/bjoc.10.51
- display broad absorption bands and computations suggest, that novel types of panchromatic absorbing bichromophores should be readily available by ligating the second chromophore via the electronically nonperturbing N-sulfonyl moiety. Synthetic, photophysical, and computational studies addressing
Graphical Abstract
Figure 1: Linear push–pull solid-state diene lumophores with conformationally flexible and fixed acceptor moi...
Scheme 1: Three-component synthesis of 1-styryleth-2-enylideneindolones 8.
Figure 2: DFT-computed energy differences of the stereoisomers of 2Z,4Z-8a and 2Z,4E-8a.
Scheme 2: Three-component synthesis of 4-(1,3,3-trimethylindolin-2-ylidene)but-2-en-1-ylideneindolones 10.
Figure 3: DFT-computed energy differences of the stereoisomers of 10a and 10h.
Scheme 3: Mechanistic rationale of the three-component sequence furnishing the 1-styryleth-2-enylideneindolon...
Figure 4: DFT-computed (B3LYP functional, 6-31G* basis set) HOMO (left) and LUMO (right) of merocyanine 8a.
Figure 5: Absorption and emission spectrum of the dropcasted film of compound 8a (recorded at room temperatur...
Figure 6: Absorption spectrum of the dropcasted film of compound 10d (recorded at room temperature, normalize...
Figure 7: Absorption spectra of compound 10h in dichloromethane (right trace) and of the dropcasted film (lef...
Figure 8: DFT-computed (B3LYP functional, 6-311G(d,p) basis set) FMOs (HOMO, bottom; LUMO (center), and LUMO+...
Gold-catalyzed intermolecular hydroamination of allenes with sulfonamides
- Chen Zhang,
- Shao-Qiao Zhang,
- Hua-Jun Cai and
- Dong-Mei Cui
Beilstein J. Org. Chem. 2013, 9, 1045–1050, doi:10.3762/bjoc.9.117
- ; hydroamination; N-sulfonyl; selectivity; sulfonamide; Introduction Hydroamination of an N–H bond across a C–C unsaturated bond represents one of the most effective and atom-economical methods to prepare amine derivatives [1][2][3][4][5]. In the case of using allenes, this reaction can lead to allylamines, which
Graphical Abstract
Figure 1: The X-ray structure of 3l.
Figure 2: The X-ray structure of 3n.
Scheme 1: Proposed mechanism for the hydroamination of allenes.
Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols
- Rajendra Surasani,
- Dipak Kalita,
- A. V. Dhanunjaya Rao and
- K. B. Chandrasekhar
Beilstein J. Org. Chem. 2012, 8, 2004–2018, doi:10.3762/bjoc.8.227
- without N-protection (1a, Table 2, entry 1). When the reaction was carried out with N-sulfonyl-protected 4-bromo-7-azaindole 1b only the desulfonated product (Table 2, entry 2) was obtained. It is worth mentioning that the N-sulfonyl protected 7-azaindole 1b was efficiently deprotected under basic
Graphical Abstract
Figure 1: Representative drug candidates of amino-azaindole and phenyl-azaindole containing motifs.
Scheme 1: Cross coupling of 4-bromo-7-azaindole with amides, amines, amino acid esters and phenols.
Approaches towards the synthesis of 5-aminopyrazoles
- Ranjana Aggarwal,
- Vinod Kumar,
- Rajiv Kumar and
- Shiv P. Singh
Beilstein J. Org. Chem. 2011, 7, 179–197, doi:10.3762/bjoc.7.25
- 20 on treatment with 5% HCl in ethanol underwent cyclization to afford 21. A novel solid phase synthesis of some 5-aminopyrazoles 24 and their N-acyl and N-sulfonyl derivatives has recently been reported by Watson et al. [38] via the resin supported β-ketonitriles 22 (Scheme 7). The resin supported
Graphical Abstract
Figure 1: Pharmacologically active 5-aminopyrazoles.
Scheme 1: General equation for the condensation of β-ketonitriles with hydrazines.
Scheme 2: Reaction of hydrazinoheterocycles with α-phenyl-β-cyanoketones (4).
Scheme 3: Condensation of cyanoacetaldehyde (7) with hydrazines.
Scheme 4: Synthesis of 5-aminopyrazoles and their sulfonamide derivatives.
Scheme 5: Synthesis of 5-aminopyrazoles, containing a cyclohexylmethyl- or phenylmethyl- sulfonamido group at...
Scheme 6: Regioselective synthesis of 3-amino-2-alkyl (or aryl) thieno[3,4-c]pyrazoles 19.
Scheme 7: Solid supported synthesis of 5-aminopyrazoles.
Scheme 8: Synthesis of 5-aminopyrazoles from resin supported enamine nitrile 25 as the starting material.
Scheme 9: Two-step “catch and release” solid-phase synthesis of 3,4,5-trisubstituted pyrazoles.
Scheme 10: Synthesis of pyrazolo[5,1-d][1,2,3,5]tetrazine-4(3H)-ones.
Scheme 11: Synthesis of the 5,5-ring system, imidazo[1,2-b]pyrazol-2-ones.
Scheme 12: Synthesis of 5-amino-3-(pyrrol-2-yl)pyrazole-4-carbonitrile.
Scheme 13: Synthesis of N-(1,3-diaryl-1H-pyrazol-5-yl)benzamide.
Scheme 14: Synthesis of 3,7-bis(arylazo)-6-methyl-2-phenyl-1H-imidazo[1,2-b]pyrazoles.
Scheme 15: Synthesis of 3,5-diaminopyrazole.
Scheme 16: Synthesis of 5-amino-4-cyanopyrazole and 5-amino-3-hydrazinopyrazole.
Scheme 17: Synthesis of 3,5-diaminopyrazoles with substituted malononitriles.
Scheme 18: Synthesis of 3,5-diamino-4-oximinopyrazole.
Scheme 19: Synthesis of 4-arylazo-3,5-diaminopyrazoles.
Scheme 20: Synthesis of 3- or 5-amino-4-cyanopyrazoles.
Scheme 21: Synthesis of triazenopyrazoles.
Scheme 22: Synthesis of 5(3)-aminopyrazoles.
Scheme 23: Synthesis of 3-substituted 5-amino-4-cyanopyrazoles.
Scheme 24: Synthesis of 2-{[(1-acetyl-4-cyano-1H-pyrazol-5-yl)amino]methylene}malononitrile.
Scheme 25: Synthesis of 5-aminopyrazole carbodithioates and 5-amino-3-arylamino-1-phenylpyrazole-4-carboxamide...
Scheme 26: Synthesis of 5-amino-4-cyanopyrazoles.
Scheme 27: Synthesis of thiazolylpyrazoles.
Scheme 28: Synthesis of 5-amino-1-heteroaryl-3-methyl/aryl-4-cyanopyrazoles.
Scheme 29: Synthesis of 5-amino-3-methylpyrazole-4-carboxamide.
Scheme 30: Synthesis of 4-acylamino-3(5)-amino-5(3)-arylsulfanylpyrazoles.
Scheme 31: Synthesis of 5-amino-1-aryl-4-diethoxyphosphoryl-3-halomethylpyrazoles.
Scheme 32: Synthesis of substituted 5-amino-3-trifluoromethylpyrazoles 114 and 118.
Scheme 33: Solid-support synthesis of 5-N-alkylamino and 5-N-arylaminopyrazoles.
Scheme 34: Synthesis of 5-amino-1-cyanoacetyl-3-phenyl-1H-pyrazole.
Scheme 35: Synthesis of 3-substituted 5-amino-1-aryl-4-(benzothiazol-2-yl)pyrazoles.
Scheme 36: Synthesis of 5-amino-4-carbethoxy-3-methyl-1-(4-sulfamoylphenyl)pyrazole.
Scheme 37: Synthesis of inhibitors of hsp27-phosphorylation and TNFa-release.
Scheme 38: Synthesis of the diglycylpyrazole 142.
Scheme 39: Synthesis of 5-amino-1-aryl-4-benzoylpyrazole derivatives.
Scheme 40: Synthesis of 4-benzoyl-3,5-diamino-1-(2-cyanoethyl)pyrazole.
Scheme 41: Synthesis of the 5-aminopyrazole derivative 150.
Scheme 42: Synthesis of 3,5-diaminopyrazoles 153.
Scheme 43: Synthesis of 5-aminopyrazoles derivatives 155 via lithiated intermediates.
Scheme 44: Synthesis of 5-amino-4-(1,2,4-oxadiazol-5-yl)-pyrazoles 157.
Scheme 45: Synthesis of a 5-aminopyrazole with anticonvulsant activity.
Scheme 46: Synthesis of tetrasubstituted 5-aminopyrazole derivatives.
Scheme 47: Synthesis of substituted 5-aminopyrazoles from hydrazonoyl halides.
Scheme 48: Synthesis of 3-amino-5-phenylpyrazoles from isothiazoles.
Scheme 49: Synthesis of 5-aminopyrazoles via ring transformation.
Diastereoselective functionalisation of benzo-annulated bicyclic sultams: Application for the synthesis of cis-2,4-diarylpyrrolidines
- Susan Kelleher,
- Pierre-Yves Quesne and
- Paul Evans
Beilstein J. Org. Chem. 2009, 5, No. 69, doi:10.3762/bjoc.5.69
- ). Functionalisation of the N-sulfonyl enamines 5a and 5b was subsequently studied with the ultimate aim of introducing substituents, in a stereoselective fashion, to the masked pyrrolidine ring. Thus, epoxidation of 5a and 5b (Scheme 3) using m-CPBA proceeded smoothly for both substrates and as hoped, occurred under
- hoped for alcohol 8. A similar outcome was observed under both Sakurai-type conditions and treatment with potassium cyanide. It seems probable that these failures reflect a combination of the inability of the N-lone pair to stabilise the developing α-carbocation (the resultant N-sulfonyl iminium ion
- the N-sulfonyl group and its ability to stabilise an α-carbocation, N-sulfonyl iminium ions have been implicated in many instances [18][19][21]. However, in this particular case, based on the conformation of the rigid bicyclic molecule, this mode of stabilisation is not feasible. An alternative
Graphical Abstract
Scheme 1: The diastereoselective intramolecular Heck-hydrogenation and double reduction sequence as a means o...
Scheme 2: The synthesis of 5a and 5b by an intramolecular Heck cyclisation reaction.
Scheme 3: Diastereoselective epoxidation of 5a and 5b.
Figure 1: X-ray structure of 7a; including a view along the S=O···C–O axis (Diamond representations) [O2···C9...
Scheme 4: cis-Selective dibromination of 5a (NOE indicated by arrows).
Figure 2: X-ray crystal structure of 13a (Diamond representation).
Scheme 5: Dibromination studies of 5b.
Figure 3: X-ray crystal structures of 18b and 19b (Diamond representations).
Scheme 6: Possible explanation for the products formed in the dibromination of 5a and 5b.
Scheme 7: Lithiation–CO2 quench approach for the synthesis of 26 from vinyl bromide 24a.
Figure 4: X-ray structure of 26 (Diamond representation).
Scheme 8: Suzuki–Miyaura cross-coupling of 24a and the diastereoselective hydrogenation of the resultant styr...
Figure 5: X-ray crystal structure of 31 (Diamond representation).
Scheme 9: Attempted sulfonamide double reduction of compounds 31–34.
Pd/C- Mediated synthesis of indoles in water
- Mohosin Layek,
- Udaya Lakshmi,
- Dipak Kalita,
- Deepak K. Barange,
- Aminul Islam,
- K. Mukkanti and
- Manojit Pal
Beilstein J. Org. Chem. 2009, 5, No. 46, doi:10.3762/bjoc.5.46
- interest. Preparation of 2,5-disubstituted indole. Preparation of compound C. Pd/C-Catalyzed synthesis of 2,5-disubstituted N-sulfonyl-indoles in aqueous media.a Supporting Information Supporting Information File 78: Spectral data of 2-substituted indoles 3a–s. Acknowledgements The authors thank Dr. V
Graphical Abstract
Figure 1: Design of novel indole derivative C of pharmacological interest.
Scheme 1: Preparation of 2,5-disubstituted indole.
Scheme 2: Preparation of compound C.
