메뉴 건너뛰기




Volumn 38, Issue 11, 2008, Pages 1784-1791

Mild and efficient Michael addition of activated olefins to indoles using TBAB as a catalyst: Synthesis of 3-substituted indoles

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; INDOLE DERIVATIVE;

EID: 45749126599     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910801989600     Document Type: Article
Times cited : (7)

References (29)
  • 1
    • 33947461054 scopus 로고
    • The reaction of substituted indoles with methyl vinyl ketone. New synthesis of 2-methylcarbazole
    • (a) Szmuszkoyicz, J. The reaction of substituted indoles with methyl vinyl ketone. New synthesis of 2-methylcarbazole. J. Am. Chem. Soc. 1957, 79, 2819;
    • (1957) J. Am. Chem. Soc , vol.79 , pp. 2819
    • Szmuszkoyicz, J.1
  • 2
    • 0001322030 scopus 로고
    • ZrCl4 Catalyzed highly selective and efficient Michael addition of heterocyclic enamines with alpha, beta-unsaturated olefins
    • (b) Noland, W. E.; Christensen, G. M.; Sauer, G. L.; Dutton, G. G. S. ZrCl4 Catalyzed highly selective and efficient Michael addition of heterocyclic enamines with alpha, beta-unsaturated olefins. J. Am. Chem. Soc. 1955, 77, 456;
    • (1955) J. Am. Chem. Soc , vol.77 , pp. 456
    • Noland, W.E.1    Christensen, G.M.2    Sauer, G.L.3    Dutton, G.G.S.4
  • 3
    • 0000242844 scopus 로고
    • Reactions on solid supports part IV: Reactions of α,β-unsaturated carbonyl compounds with indoles using clay as catalyst
    • (c) Iqbal, Z.; Jackson, A. H.; Rao, K. R. N. Reactions on solid supports part IV: Reactions of α,β-unsaturated carbonyl compounds with indoles using clay as catalyst. Tetrahedron Lett. 1988, 29, 2577.
    • (1988) Tetrahedron Lett , vol.29 , pp. 2577
    • Iqbal, Z.1    Jackson, A.H.2    Rao, K.R.N.3
  • 4
    • 19544366287 scopus 로고    scopus 로고
    • Auxin: Regulation, action, and interaction
    • Woodward, A. N.; Bartel, B. Auxin: Regulation, action, and interaction. Ann. Bot. 2005, 95, 707.
    • (2005) Ann. Bot , vol.95 , pp. 707
    • Woodward, A.N.1    Bartel, B.2
  • 6
    • 0035863281 scopus 로고    scopus 로고
    • Oxidative activation of indole-3-acetic acids to cytotoxic species - a potential new role for plant auxins in cancertherapy
    • (a) Folkes, L. K.; Wardman, P. Oxidative activation of indole-3-acetic acids to cytotoxic species - a potential new role for plant auxins in cancertherapy. Biochem. Pharm. 2001, 61, 129;
    • (2001) Biochem. Pharm , vol.61 , pp. 129
    • Folkes, L.K.1    Wardman, P.2
  • 7
    • 0035554093 scopus 로고    scopus 로고
    • Horseradish peroxidase-mediated gene therapy: Choice of prodrugs in oxic and anoxic tumor conditions
    • (b) Greco, O.; Rossiter, S.; Kanthou, C.; Folkes, L. K.; Wardman, P.; Tozer, G. M.; Dachs, G. U. Horseradish peroxidase-mediated gene therapy: choice of prodrugs in oxic and anoxic tumor conditions. Mol. Cancer Ther. 2001, 1, 151.
    • (2001) Mol. Cancer Ther , vol.1 , pp. 151
    • Greco, O.1    Rossiter, S.2    Kanthou, C.3    Folkes, L.K.4    Wardman, P.5    Tozer, G.M.6    Dachs, G.U.7
  • 8
    • 0036739952 scopus 로고    scopus 로고
    • On inventing reactions for atom economy
    • (a) Trost, B. M. On inventing reactions for atom economy. Acc. Chem. Res. 2002, 35, 695;
    • (2002) Acc. Chem. Res , vol.35 , pp. 695
    • Trost, B.M.1
  • 9
    • 0026418434 scopus 로고
    • The atom economy-a search for synthetic efficiency
    • (b) Trost, B. M. The atom economy-a search for synthetic efficiency. Science 1991, 254, 1471.
    • (1991) Science , vol.254 , pp. 1471
    • Trost, B.M.1
  • 10
    • 0030687930 scopus 로고    scopus 로고
    • The preparation of synthetically useful carbonyl-protected α- and β- lithio ketones via reductive lithiation
    • (a) Zhu, S.; Cohen, T. The preparation of synthetically useful carbonyl-protected α- and β- lithio ketones via reductive lithiation. Tetrahedron 1997, 53, 17607;
    • (1997) Tetrahedron , vol.53 , pp. 17607
    • Zhu, S.1    Cohen, T.2
  • 11
    • 0000163641 scopus 로고
    • Addition of aromatic thiols to conjugated cycloalkenones, catalyzed by chiral beta-hydroxy amines. A mechanistic study of homogeneous catalytic asymmetric synthesis
    • (b) Hiemstra, H.; Wiberg, H. Addition of aromatic thiols to conjugated cycloalkenones, catalyzed by chiral beta-hydroxy amines. A mechanistic study of homogeneous catalytic asymmetric synthesis. J. Am. Chem. Soc. 1981, 103, 417;
    • (1981) J. Am. Chem. Soc , vol.103 , pp. 417
    • Hiemstra, H.1    Wiberg, H.2
  • 12
    • 0000078268 scopus 로고
    • The enantioselective michael addition of thiols to cycloalkenones by using (2S, 4S)-2-anilinomethyl-1-ethyl- 4-hydroxypyrrolidine as chiral catalyst
    • (c) Suzuki, K.; Ikekawa, A.; Mukaiyama, T. The enantioselective michael addition of thiols to cycloalkenones by using (2S, 4S)-2-anilinomethyl-1-ethyl- 4-hydroxypyrrolidine as chiral catalyst. Bull. Soc. Chem. Jpn. 1982, 55, 3277;
    • (1982) Bull. Soc. Chem. Jpn , vol.55 , pp. 3277
    • Suzuki, K.1    Ikekawa, A.2    Mukaiyama, T.3
  • 13
    • 0000241370 scopus 로고
    • Asymmetric michael addition of thiophenol to maleic acid esters
    • (d) Yamashata, H.; Mukaiyama, T. Asymmetric michael addition of thiophenol to maleic acid esters. Chem. Lett. 1985, 363;
    • (1985) Chem. Lett , pp. 363
    • Yamashata, H.1    Mukaiyama, T.2
  • 14
    • 0032577033 scopus 로고    scopus 로고
    • Catalytic Michael addition of thiols to, β-unsaturated carbonyl compounds: Asymmetric Michael additions and asymmetric protonations
    • (e) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. Catalytic Michael addition of thiols to, β-unsaturated carbonyl compounds: Asymmetric Michael additions and asymmetric protonations. J. Am. Chem. Soc. 1998, 120, 4043;
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 4043
    • Emori, E.1    Arai, T.2    Sasai, H.3    Shibasaki, M.4
  • 15
    • 34248566954 scopus 로고    scopus 로고
    • Sulfamic acid-catalyzed Michael addition of indoles and pyrrole to electron-deficient nitroolefins under solvent-free condition
    • (f) Tao An, L.; Ping Zou, J.; Li Zhang, L.; Zhang, Y. Sulfamic acid-catalyzed Michael addition of indoles and pyrrole to electron-deficient nitroolefins under solvent-free condition. Tetrahedron Lett. 2007, 48, 4297.
    • (2007) Tetrahedron Lett , vol.48 , pp. 4297
    • Tao An, L.1    Ping Zou, J.2    Li Zhang, L.3    Zhang, Y.4
  • 16
    • 0001586671 scopus 로고
    • Friedel-Crafts alkylation
    • 1st edn, Trost, B. M. and Fleming, I, Eds, Pergamon: Oxford
    • (a) Olah, G. A.; Krishnamurty, R.; Prakash, G. K. S. Friedel-Crafts alkylation. In Comprehensive Organic Synthesis, 1st edn.; Trost, B. M. and Fleming, I., Eds.; Pergamon: Oxford, 1991, Vol. III, p. 293.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 293
    • Olah, G.A.1    Krishnamurty, R.2    Prakash, G.K.S.3
  • 17
    • 0036284388 scopus 로고    scopus 로고
    • A practical indium tribromide catalysed addition of indoles to nitroalkenes in aqueous media
    • InBr3
    • 3: Bandini, M.; Melchiorre, P.; Melloni, A.; Umani-Ronchi, A. A practical indium tribromide catalysed addition of indoles to nitroalkenes in aqueous media. Synthesis 2002, 1110;
    • (2002) Synthesis , pp. 1110
    • Bandini, M.1    Melchiorre, P.2    Melloni, A.3    Umani-Ronchi, A.4
  • 19
    • 0842265861 scopus 로고    scopus 로고
    • 2: Komoto, I.; Kobayashi, S. Lewis acid catalysis in supercritical carbon dioxide. Use of poly(-ethylene glycol) derivatives and perfluoroalkylbenzenes as surfactant molecules which enable efficient catalysis in ScCO2. J. Org. Chem. 2004, 69, 680;
    • 2: Komoto, I.; Kobayashi, S. Lewis acid catalysis in supercritical carbon dioxide. Use of poly(-ethylene glycol) derivatives and perfluoroalkylbenzenes as surfactant molecules which enable efficient catalysis in ScCO2. J. Org. Chem. 2004, 69, 680;
  • 20
    • 0001875106 scopus 로고    scopus 로고
    • 3: Harrington, P. E.; Kerr, M. A. Reaction of indoles with electron deficient olefins catalyzed by Yb(OTf)3 3H2O. Synlett 1996, 1047;
    • 3: Harrington, P. E.; Kerr, M. A. Reaction of indoles with electron deficient olefins catalyzed by Yb(OTf)3 3H2O. Synlett 1996, 1047;
  • 21
    • 18144392668 scopus 로고    scopus 로고
    • Samarium triiodide-catalyzed conjugate addition of indoles with electron-deficient olefins
    • SmI3
    • 3: Zhan, Z.-P.; Yang, R.-F.; Lang, K. Samarium triiodide-catalyzed conjugate addition of indoles with electron-deficient olefins. Tetrahedron Lett. 2005, 46, 3859;
    • (2005) Tetrahedron Lett , vol.46 , pp. 3859
    • Zhan, Z.-P.1    Yang, R.-F.2    Lang, K.3
  • 22
    • 14544291479 scopus 로고    scopus 로고
    • 2: Bartoli, G.; Bosco, M.; Giuli, S.; Giuliani, A.; Lucarelli, L.; Marcantoni, E.; Sambri, L.; Torregiani, E. Efficient preparation of 2-Indolyl-1-nitroalkane derivatives employing nitroalkenes as versatile michael acceptors: New practical linear approach to alkyl 9H-β-Carboline-4-carboxylate. J. Org. Chem. 2005, 70, 1941;
    • 2: Bartoli, G.; Bosco, M.; Giuli, S.; Giuliani, A.; Lucarelli, L.; Marcantoni, E.; Sambri, L.; Torregiani, E. Efficient preparation of 2-Indolyl-1-nitroalkane derivatives employing nitroalkenes as versatile michael acceptors: New practical linear approach to alkyl 9H-β-Carboline-4-carboxylate. J. Org. Chem. 2005, 70, 1941;
  • 23
    • 14644416538 scopus 로고    scopus 로고
    • 2O: Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F. The facile and efficient Michael addition of indoles and pyrrole to α,β-unsaturated electron-deficient compounds catalyzed by aluminium dodecyl sulfate trihydrate [Al(DS)3]·3H2O in water. Chem. Commun. 2005, 6, 789;
    • 2O: Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F. The facile and efficient Michael addition of indoles and pyrrole to α,β-unsaturated electron-deficient compounds catalyzed by aluminium dodecyl sulfate trihydrate [Al(DS)3]·3H2O in water. Chem. Commun. 2005, 6, 789;
  • 24
    • 31144455178 scopus 로고    scopus 로고
    • Asymmetric friedel-crafts alkylations of indoles with nitroalkenes catalyzed by Zn(II)-bisoxazoline complexes
    • (h) Jia, Y.-X.; Zhu, S.-F.; Yang, Y.; Zhou, Q.-L. Asymmetric friedel-crafts alkylations of indoles with nitroalkenes catalyzed by Zn(II)-bisoxazoline complexes. J. Org. Chem. 2006, 71, 75;
    • (2006) J. Org. Chem , vol.71 , pp. 75
    • Jia, Y.-X.1    Zhu, S.-F.2    Yang, Y.3    Zhou, Q.-L.4
  • 25
    • 27344435447 scopus 로고    scopus 로고
    • Catalytic enantioselective addition of indoles to arylnitroalkenes: An effective route to enantiomerically enriched tryptamine precursors
    • (i) Bandini, M.; Garelli, A.; Rovinetti, M.; Tommasi, S.; Umani-Ronchi, A. Catalytic enantioselective addition of indoles to arylnitroalkenes: An effective route to enantiomerically enriched tryptamine precursors. Chirality 2005, 17, 522;
    • (2005) Chirality , vol.17 , pp. 522
    • Bandini, M.1    Garelli, A.2    Rovinetti, M.3    Tommasi, S.4    Umani-Ronchi, A.5
  • 26
    • 21544459927 scopus 로고    scopus 로고
    • Microwave-accelerated samarium triiodide catalyzed conjugate addition of indoles with electron-deficient olefins
    • (j) Zhan, Z. P.; Lang, K. Microwave-accelerated samarium triiodide catalyzed conjugate addition of indoles with electron-deficient olefins. Synlett 2005, 1551.
    • (2005) Synlett , pp. 1551
    • Zhan, Z.P.1    Lang, K.2
  • 29
    • 1842634778 scopus 로고    scopus 로고
    • Effect of quaternary ammonium salts on the hydrolysis of N-glutaryl-l-phenylalanine catalysed by β-chymotrypsin
    • and references cited therein
    • Viparelli, P.; Alfani, F.; Gallifuoco, A.; Cantarella, M. Effect of quaternary ammonium salts on the hydrolysis of N-glutaryl-l-phenylalanine catalysed by β-chymotrypsin. J. Mol. Catal. B: Enzymatic 2004, 28, 101, and references cited therein.
    • (2004) J. Mol. Catal. B: Enzymatic , vol.28 , pp. 101
    • Viparelli, P.1    Alfani, F.2    Gallifuoco, A.3    Cantarella, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.