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Volumn 14, Issue 2, 2010, Pages 385-392

The Michael addition of indoles and pyrrole to α-, β-unsaturated ketones and double-conjugate 1,4-addition of indoles to symmetric enones promoted by pulverization-activation method and Thia-Michael addition catalyzed by wet cyanuric chloride

Author keywords

A unsaturated compounds; Conjugate 1,4 addition; Solvent free; TCT

Indexed keywords

2,4,6 TRICHLORO (1,3,5) TRIAZINE; CYANURIC ACID; ELECTROPHILE; INDOLE DERIVATIVE; KETONE DERIVATIVE; NUCLEOPHILE; PYRROLE DERIVATIVE; SOLVENT; THIOL DERIVATIVE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG; CYANURIC CHLORIDE; KETONE;

EID: 77954666517     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-009-9184-2     Document Type: Article
Times cited : (14)

References (37)
  • 2
    • 0004180584 scopus 로고
    • Glasby JS (ed). Plenum Press, New York
    • Glasby JS (ed) (1975) Encyclopedia of the alkaloids. Plenum Press, New York
    • (1975) Encyclopedia of the Alkaloids
  • 4
    • 85064667331 scopus 로고
    • Rare earth metal trifluromethanesulfonates as water-tolerant lewis acid catalysis in organic synthesis
    • Kobayashi S (1994) Rare earth metal trifluromethanesulfonates as water-tolerant lewis acid catalysis in organic synthesis. Synlett 689-701
    • (1994) Synlett , pp. 689-701
    • Kobayashi, S.1
  • 5
    • 0037459683 scopus 로고    scopus 로고
    • Bismuth nitrate-catalyzed versatile Michael reactions
    • doi:10.1021/ jo026550s
    • Srivastava N, Banik BK (2003) Bismuth nitrate-catalyzed versatile Michael reactions. J Org Chem 68: 2109-2114. doi:10.1021/ jo026550s
    • (2003) J Org Chem , vol.68 , pp. 2109-2114
    • Srivastava, N.1    Banik, B.K.2
  • 6
    • 0025758355 scopus 로고
    • Surface-mediated solid phase Michael reaction: dramatic acceleration on alumina
    • doi:10.1016/0040-4039(91)85093-K
    • Ranu BC, Bhar S, Sarkar DC (1991) Surface-mediated solid phase Michael reaction: dramatic acceleration on alumina. Tetrahedron Lett 32: 2811-2812. doi:10.1016/0040-4039(91)85093-K
    • (1991) Tetrahedron Lett , vol.32 , pp. 2811-2812
    • Ranu, B.C.1    Bhar, S.2    Sarkar, D.C.3
  • 7
    • 0348225064 scopus 로고    scopus 로고
    • Highly efficient mechanochemical reactions of 1,3-dicarbonyl compounds with chalcones and azachalcones catalyzed by potassium carbonate
    • doi:10.1055/s-2003-43350
    • Zhang Z, Dong YW, Wang GW, Komatsu K (2004) Highly efficient mechanochemical reactions of 1,3-dicarbonyl compounds with chalcones and azachalcones catalyzed by potassium carbonate. Synlett 61-64. doi:10.1055/s-2003-43350
    • (2004) Synlett , pp. 61-64
    • Zhang, Z.1    Dong, Y.W.2    Wang, G.W.3    Komatsu, K.4
  • 8
    • 0025893974 scopus 로고
    • Rhodium-catalyzed Michael additions of activated nitriles to a-,β-unsaturated ester
    • doi:10.1016/0040-4039(91)85092-J
    • Paganelli S, Schionato A, Botteghi C (1991) Rhodium-catalyzed Michael additions of activated nitriles to a-, β-unsaturated ester. Tetrahedron Lett 32 : 2807-2810. doi:10.1016/0040- 4039(91)85092-J
    • (1991) Tetrahedron Lett , vol.32 , pp. 2807-2810
    • Paganelli, S.1    Schionato, A.2    Botteghi, C.3
  • 9
    • 0032537660 scopus 로고    scopus 로고
    • 1 -O-enolatoruthenium(II) complexes derived from Ru(cod)(cot), diphosphine, and dimethyl malonate
    • doi:10.1016/S0040-4039(98)01023-1025
    • Alvarez SG, Hasegawa S, Hirano M, Komiya S (1998) Michael reactions promoted by ?1 - O-enolatoruthenium(II) complexes derived from Ru(cod)(cot), diphosphine, and dimethyl malonate. Tetrahedron Lett 39: 5209-5212. doi:10.1016/S0040- 4039(98)01023-1025
    • (1998) Tetrahedron Lett , vol.39 , pp. 5209-5212
    • Alvarez, S.G.1    Hasegawa, S.2    Hirano, M.3    Komiya, S.4
  • 10
    • 0025146306 scopus 로고
    • Dual catalysis of the Michael reaction
    • DOI 10.1016/S0040-4039(00)97754-2
    • Laszlo P, Montaufier MT, Randriamahefa SL (1990) Dual catalysis of the Michael reaction. Tetrahedron Lett 31: 4867-4870. doi:10.1016/S0040-4039(00) 97754-2 (Pubitemid 20251230)
    • (1990) Tetrahedron Letters , vol.31 , Issue.34 , pp. 4867-4870
    • Laszlo, P.1    Montaufier, M.-T.2    Lalatiana Randriamahefa, S.3
  • 11
    • 0035801884 scopus 로고    scopus 로고
    • Enantioselective Michael reaction of malonates and chalcones by phase-transfer catalysis using chiral quaternary ammonium salt
    • DOI 10.1016/S0040-4039(01)01237-0, PII S0040403901012370
    • Kim DY, Huh SC, Kim SM (2001) EnantioselectiveMichael reaction of malonates and chalcones by phase-transfer catalysis using chiral quaternary ammonium salt. Tetrahedron Lett 42: 6299-6301. doi:10.1016/S0040-4039(01)01237-0 (Pubitemid 32772677)
    • (2001) Tetrahedron Letters , vol.42 , Issue.36 , pp. 6299-6301
    • Kim, D.Y.1    Huh, S.C.2    Kim, S.M.3
  • 13
    • 15244344075 scopus 로고    scopus 로고
    • Indium(III) chloride-catalyzed Michael addition of thiols to chalcones: A remarkable solvent effect
    • Ranu BC, Dey SS, Samanta S (2005) Indium(III) chloride-catalyzed Michael addition of thiols to chalcones: a remarkable solvent effect. Arkivoc 3:44-50
    • (2005) Arkivoc , vol.3 , pp. 44-50
    • Ranu, B.C.1    Dey, S.S.2    Samanta, S.3
  • 15
    • 20544463219 scopus 로고    scopus 로고
    • Iodine-catalyzed Michael addition of mercaptans to a, β-unsaturated ketones under solvent-free conditions
    • doi:10. 1016/j.tetlet.2005.05.099
    • Chu C, Gao S, Sastry MNV, Yao C (2005) Iodine-catalyzed Michael addition of mercaptans to a, β-unsaturated ketones under solvent-free conditions. Tetrahedron Lett 46: 4971-4974. doi:10. 1016/j.tetlet.2005.05.099
    • (2005) Tetrahedron Lett , vol.46 , pp. 4971-4974
    • Chu, C.1    Gao, S.2    Sastry, M.N.V.3    Yao, C.4
  • 16
    • 0037842734 scopus 로고    scopus 로고
    • 3
    • DOI 10.1016/S0040-4039(03)01089-X
    • Mujahid Alam M, Varala R, Adapa SR (2003) Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3. Tetrahedron Lett 44: 5115-5119. doi:10.1016/S0040- 4039(03)01089-X (Pubitemid 36694923)
    • (2003) Tetrahedron Letters , vol.44 , Issue.27 , pp. 5115-5119
    • Alam, M.M.1    Varala, R.2    Adapa, S.R.3
  • 17
    • 33646428647 scopus 로고    scopus 로고
    • Perchloric acid impregnated on silica gel (HClO4/SiO2): A versatile catalyst for Michael addition of thiols to the electron-deficient alkenes
    • doi:10.1002/ejoc.200600006
    • Khan AT, Ghosh S, Choudhury LH (2006) Perchloric acid impregnated on silica gel (HClO4/SiO2): a versatile catalyst for Michael addition of thiols to the electron-deficient alkenes. Eur J Org Chem 2226-2231. doi:10.1002/ejoc. 200600006
    • (2006) Eur J Org Chem , pp. 2226-2231
    • Khan, A.T.1    Ghosh, S.2    Choudhury, L.H.3
  • 18
    • 33749245641 scopus 로고    scopus 로고
    • Gallium(III) triiodide catalyzed conjugate addition of indoles with α,β-unsaturated ketones
    • DOI 10.1016/j.tetlet.2006.08.108, PII S0040403906017382
    • Huang ZH, Zou JP, Jiang WQ (2006) Gallium(III) triiodide catalyzed conjugate addition of indoles with a, β-unsaturated ketones. Tetrahedron Lett 47: 7965-7968. doi:10.1016/j.tetlet.2006.08.108 (Pubitemid 44485151)
    • (2006) Tetrahedron Letters , vol.47 , Issue.45 , pp. 7965-7968
    • Huang, Z.-H.1    Zou, J.-P.2    Jiang, W.-Q.3
  • 19
    • 10044253193 scopus 로고    scopus 로고
    • An expeditious synthesis of β-indolylketones catalyzed by p-toluenesulfonic acid (PTSA) using ultrasonic irradiation
    • doi:10. 1016/j.ultsonch.2004.05.003
    • Ji SJ, Wang SY (2005) An expeditious synthesis of β-indolylketones catalyzed by p-toluenesulfonic acid (PTSA) using ultrasonic irradiation. Ultrason Sonochem 12: 339-343. doi:10. 1016/j.ultsonch.2004.05.003
    • (2005) Ultrason Sonochem , vol.12 , pp. 339-343
    • Ji, S.J.1    Wang, S.Y.2
  • 20
    • 34248566954 scopus 로고    scopus 로고
    • Sulfamic acid-catalyzed Michael addition of indoles and pyrrole to electron-deficient nitroolefins under solvent-free condition
    • DOI 10.1016/j.tetlet.2007.04.011, PII S0040403907006636
    • An LT, Zou JP, Zhang LL, Zhang Y (2007) Sulfamic acid-catalyzed Michael addition of indoles and pyrrole to electron-deficient nitroolefins under solvent-free condition. Tetrahedron Lett 48: 4297-4300. doi:10.1016/j.tetlet. 2007.04.011 (Pubitemid 46754374)
    • (2007) Tetrahedron Letters , vol.48 , Issue.24 , pp. 4297-4300
    • An, L.-T.1    Zou, J.-P.2    Zhang, L.-L.3    Zhang, Y.4
  • 21
    • 34247214640 scopus 로고    scopus 로고
    • III-catalyzed double-conjugate 1,4-addition of indoles to symmetric enones
    • DOI 10.1016/j.molcata.2007.01.038, PII S1381116907000714
    • Tabatabaeian K, Mamaghani M, Mahmoodi NO, Khorshidi A (2007) RuIII-catalyzed double-conjugate 1,4-addition of indoles to symmetric enones. J Mol Catal A Chem 270: 112-116. doi:10.1016/j.molcata.2007.01.038 (Pubitemid 46618048)
    • (2007) Journal of Molecular Catalysis A: Chemical , vol.270 , Issue.1-2 , pp. 112-116
    • Tabatabaeian, K.1    Mamaghani, M.2    Mahmoodi, N.O.3    Khorshidi, A.4
  • 22
    • 39349098075 scopus 로고    scopus 로고
    • Ammonium chloride-catalyzed carbon-sulfur bond formation in water
    • DOI 10.1016/j.catcom.2007.10.011, PII S1566736707004505
    • Chen WY, Shi L (2008) Ammonium chloride-catalyzed carbon- sulfur bond formation in water. Catal Commun 9: 1079-1081. doi:10.1016/j.catcom.2007.10.011 (Pubitemid 351264814)
    • (2008) Catalysis Communications , vol.9 , Issue.6 , pp. 1079-1081
    • Chen, W.1    Shi, L.2
  • 23
    • 2342550664 scopus 로고    scopus 로고
    • P-BEMP: A new efficient and commercially available user-friendly and recyclable heterogeneous organocatalyst for the Michael addition of 1,3-dicarbonyl compounds
    • doi:10.1055/s-2004-815996
    • Bensa D, Constantieux T, Rodriguez J (2004) P-BEMP: a new efficient and commercially available user-friendly and recyclable heterogeneous organocatalyst for the Michael addition of 1,3-dicarbonyl compounds. Synthesis 923-927. doi:10.1055/s- 2004-815996
    • (2004) Synthesis , pp. 923-927
    • Bensa, D.1    Constantieux, T.2    Rodriguez, J.3
  • 24
    • 18744375223 scopus 로고    scopus 로고
    • Mild and regioselective bromination of aromatic compounds with N,N,N′,N′-Tetrabromobenzene-1,3-disulfonylamide and poly(N-bromobenzene-1,3-disulfonylamide)
    • DOI 10.1055/s-2005-861851, Z21504SS
    • Ghorbani-Vaghei R, Jalili H (2005) Mild and regioselective bromination of aromatic compounds with N, N, N' , N'-tetrabromobenzene- 1,3-disulfonylamide and poly(N-bromobenzene- 1,3-disulfonylamide). Synthesis 1099-1102. doi:10.1055/s-2005- 861851 (Pubitemid 40676002)
    • (2005) Synthesis , Issue.7 , pp. 1099-1102
    • Ghorbani-Vaghei, R.1    Jalili, H.2
  • 25
    • 33646774340 scopus 로고    scopus 로고
    • Poly(N-bromobenzene-1,3-disulfonamide) and N, N, N' , N'- tetrabromobenzene-1,3-disulfonamide as novel catalytic reagents for silylation of alcohols, phenols, anthiols using hexamethyldisilazane
    • doi:10.1016/j.tetlet. 2006.03.157
    • Ghorbani-Vaghei R, Zolfigol MA, Chegeny M, Veisi H (2006) Poly(N-bromobenzene-1,3-disulfonamide) and N, N, N' , N'- tetrabromobenzene-1,3- disulfonamide as novel catalytic reagents for silylation of alcohols, phenols, anthiols using hexamethyldisilazane. Tetrahedron Lett 47: 4505-4508. doi:10.1016/j.tetlet. 2006.03.157
    • (2006) Tetrahedron Lett , vol.47 , pp. 4505-4508
    • Ghorbani-Vaghei, R.1    Zolfigol, M.A.2    Chegeny, M.3    Veisi, H.4
  • 26
    • 26844484610 scopus 로고    scopus 로고
    • N,N′-Diiodo-N,N′-1,2-ethanediylbis(p-toluenesulfonamide) as a reagent for conversion of aldehydes to methyl esters
    • DOI 10.1070/MC2005v015n05ABEH002091
    • Ghorbani-Vaghei R, Shahbazee E, Veisi H (2005) N, N'-Diiodo- N, N'-1,2-ethanediylbis(p-toluenesulfonamide) as a reagent for conversion of aldehydes methyl esters. Mendeleev Commun 207-208. doi:10.1070/ MC2005v015n05ABEH002091 (Pubitemid 41463260)
    • (2005) Mendeleev Communications , Issue.5 , pp. 207-208
    • Ghorbani-Vaghei, R.1    Shahbazee, E.2    Veisi, H.3
  • 27
    • 0000090107 scopus 로고    scopus 로고
    • An efficient route to alkyl chlorides from alcohols using the complex TCT/DMF
    • doi:10.1021/ol017168p
    • Luca De L, Giacomelli G, Porcheddu A (2002) An efficient route to alkyl chlorides from alcohols using the complex TCT/DMF. Org Lett 4:553-555. doi:10.1021/ol017168p
    • (2002) Org Lett , vol.4 , pp. 553-555
    • Luca De, L.1    Giacomelli, G.2    Porcheddu, A.3
  • 28
    • 0037162857 scopus 로고    scopus 로고
    • Beckmann rearrangement of oximes under very mild conditions
    • DOI 10.1021/jo025960d
    • Luca De L, Porcheddu A Giacomelli G (2002) Beckmann rearrangement of oximes under very mild conditions. J Org Chem 67:6272-6274. doi:10.1021/ jo025960d (Pubitemid 34912999)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.17 , pp. 6272-6274
    • De Luca, L.1    Giacomelli, G.2    Porcheddu, A.3
  • 29
    • 15444377730 scopus 로고    scopus 로고
    • Microwave-assisted synthesis of isonitriles: A general simple methodology
    • DOI 10.1021/jo047924f
    • Porcheddu A, GiacomelliG, SalarisM (2005) Microwave-assisted synthesis of isonitriles: a general simplemethodology. J Org Chem 70: 2361-2363. doi:10.1021/jo047924f (Pubitemid 40395184)
    • (2005) Journal of Organic Chemistry , vol.70 , Issue.6 , pp. 2361-2363
    • Porcheddu, A.1    Giacomelli, G.2    Salaris, M.3
  • 30
    • 4544309609 scopus 로고    scopus 로고
    • A versatile and practical synthesis of bis(indolyl)methanes/bis(indolyl) glycoconjugates catalyzed by trichloro-1,3,5-triazine
    • DOI 10.1016/j.tetlet.2004.08.084, PII S0040403904017952
    • Sharma GVM, Reddy JJ, Lakshmi PS, Krishna PR (2004) A versatile and practical synthesis of bis(indolyl)methanes/bis (indolyl)glycoconjugates catalyzed by trichloro-1,3,5-triazine. Tetrahedron Lett 45: 7729-7732. doi:10.1016/j.tetlet.2004.08.084 (Pubitemid 39243360)
    • (2004) Tetrahedron Letters , vol.45 , Issue.41 , pp. 7729-7732
    • Sharma, G.V.M.1    Janardhan Reddy, J.2    Sree Lakshmi, P.3    Radha Krishna, P.4
  • 31
    • 17744400705 scopus 로고    scopus 로고
    • Novel highly potent, structurally simple γ-trifluoromethyl γ-sulfone hydroxamate inhibitor of stromelysin-1 (MMP-3)
    • DOI 10.1016/j.tetlet.2005.02.063
    • Sani M, Candiani G, Pecker F, Malpezzi L, ZandaM (2005) Novel highly potent, structurally simple γ -trifluoromethyl γ -sulfone hydroxamate inhibitor of stromelysin-1 (MMP-3). Tetrahedron Lett 46: 2393-2396. doi:10.1016/j.tetlet.2005.02.063 (Pubitemid 40576190)
    • (2005) Tetrahedron Letters , vol.46 , Issue.14 , pp. 2393-2396
    • Sani, M.1    Candiani, G.2    Pecker, F.3    Malpezzi, L.4    Zanda, M.5
  • 32
    • 18844369828 scopus 로고    scopus 로고
    • Ring-closure reactions through intramolecular substitution of thiophenoxide by oxygen and nitrogen nucleophiles: Simple stereospecific synthesis of 4,5-dihydroisoxazoles and 4,5-dihydropyrazoles
    • DOI 10.1016/j.tet.2005.03.085, PII S0040402005005685
    • Zielinska-Blajet M, Kowalczyk R, Skarzewski J (2005) Ring-closure reactions through intramolecular substitution of thiophenoxide by oxygen and nitrogen nucleophiles: simple stereospecific synthesis of 4,5-dihydroisoxazoles and 4,5-dihydropyrazoles. Tetrahedron 61: 5235-5240. doi:10.1016/j.tet.2005.03. 085 (Pubitemid 40693251)
    • (2005) Tetrahedron , vol.61 , Issue.22 , pp. 5235-5240
    • Zielinska-Blajet, M.1    Kowalczyk, R.2    Skarzewski, J.3
  • 33
    • 0021435184 scopus 로고
    • Asymmetric syntheses based on 1,3-oxathianes. 1. Scope of the reaction
    • doi:10.1021/ja00322a033
    • Eliel EL, Morris Natschke S (1984) Asymmetric syntheses based on 1,3-oxathianes. 1. Scope of the reaction. J Am Chem Soc 106: 2937-2942. doi:10.1021/ja00322a033
    • (1984) J Am Chem Soc , vol.106 , pp. 2937-2942
    • Eliel, E.L.1    Morris Natschke, S.2
  • 34
    • 23944450182 scopus 로고    scopus 로고
    • Palladium-catalyzed Michael addition of indoles to α,β- unsaturated ketones in an ionic liquid
    • DOI 10.1055/s-2005-871952, U13905ST
    • Li WJ, Lin XF, Wang J, Li GL, Wang YG (2005) Palladium-catalyzed Michael addition of indoles to a-, β-unsaturated ketones in an ionic liquid. Synlett 2003-2006. doi:10.1055/s-2005-871952 (Pubitemid 41207598)
    • (2005) Synlett , Issue.13 , pp. 2003-2006
    • Li, W.-J.1    Lin, X.-F.2    Wang, J.3    Li, G.-L.4    Wang, Y.-G.5
  • 35
    • 33947730988 scopus 로고    scopus 로고
    • Amberlyst-15: A mild, efficient and reusable heterogeneous catalyst for Michael addition of pyrroles to α,β-unsaturated ketones
    • DOI 10.1016/j.molcata.2007.01.007, PII S1381116907000301
    • Das B, Damodar K, Chowdhury NA (2007) Amberlyst-15: a mild, efficient and reusable heterogeneous catalyst for Michael addition of pyrroles to a, β-unsaturated ketones. J Mol Catal A Chem 269: 81-84. doi:10.1016/j. molcata.2007.01.007 (Pubitemid 46507872)
    • (2007) Journal of Molecular Catalysis A: Chemical , vol.269 , Issue.1-2 , pp. 81-84
    • Das, B.1    Damodar, K.2    Chowdhury, N.3
  • 36
    • 33645788615 scopus 로고    scopus 로고
    • Novel brønsted acid-catalyzed Michael-type Friedel-Crafts reactions of indoles and acetalization of aldehydes
    • doi:10.1016/j.molcata.2006.01.005
    • Zhou W, Xu LW, Yang L, Zhao PQ, Xia CG (2006) Novel brønsted acid-catalyzed Michael-type Friedel-Crafts reactions of indoles and acetalization of aldehydes. J Mol Catal A Chem 249: 129-134. doi:10.1016/j.molcata.2006.01.005
    • (2006) J Mol Catal A Chem , vol.249 , pp. 129-134
    • Zhou, W.1    Xu, L.W.2    Yang, L.3    Zhao, P.Q.4    Xia, C.G.5
  • 37
    • 34548314184 scopus 로고    scopus 로고
    • Wet cyanuric chloride catalyzed simple and efficient synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j]xanthenes
    • DOI 10.1016/j.catcom.2007.01.007, PII S1566736707000179
    • Bigdeli MA, Heravi MM, Mahdavinia GH (2007) Wet cyanuric chloride catalyzed simple and efficient synthesis of 14-aryl or alkyl-14-H-dibenzo[a, j]xanthenes. Catal Commun 8: 1595-1598. doi:10.1016/j.catcom.2007.01.007 (Pubitemid 47432861)
    • (2007) Catalysis Communications , vol.8 , Issue.11 , pp. 1595-1598
    • Bigdeli, M.A.1    Heravi, M.M.2    Hossein Mahdavinia, G.3


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