Iodine-Catalyzed Highly Efficient Synthesis of 3-Alkylated/3-Alkenylated Indoles from 1,3-Dicarbonyl Compounds

被引：16

作者：

Singh, Neetu ^{[1
]}

Singh, Krishna Nand ^{[1
]}

机构：

[1] Banaras Hindu Univ, Fac Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India

来源：

SYNLETT | 2012年 / 14期

关键词：

iodine; 3-alkenylated indoles; 1,3-dicarbonyl compounds; solvent-free; bis(indolyl)carbonyl compounds; ONE-POT SYNTHESIS; NONREARRANGED MONOTERPENOID UNIT; MOLECULAR-IODINE; SOLVENT-FREE; ALPHA; BETA-UNSATURATED KETONES; MICHAEL ADDITION; CONJUGATE ADDITION; DERIVATIVES; ALKALOIDS; MICROWAVE;

D O I：

10.1055/s-0032-1316684

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Molecular iodine has been found to be an efficient and inexpensive catalyst for the synthesis of 3-alkylated/3-alkenylated indoles in excellent yields by using different indoles and 1,3-dicarbonyl compounds at room temperature.

引用

收藏

页码：2116 / 2120

页数：5

相关论文

共 42 条

[1] Highly efficient one-pot synthesis of primary amides catalyzed by scandium(III) triflate under controlled MW [J].

Allam, Bharat Kumar ;

Singh, Krishna Nand .

TETRAHEDRON LETTERS, 2011, 52 (44) :5851-5854

[2] Antitumor activity of bis-indole derivatives [J].

Andreani, Aldo ;

Burnelli, Silvia ;

Granaiola, Massimiliano ;

Leoni, Alberto ;

Locatelli, Alessandra ;

Morigi, Rita ;

Rambaldi, Mirella ;

Varoli, Lucilla ;

Landi, Laura ;

Prata, Cecilia ;

Berridge, Michael V. ;

Grasso, Carole ;

Fiebig, Heinz-Herbert ;

Kelter, Gerhard ;

Burger, Angelika M. ;

Kunkel, Mark W. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4563-4570

[3]

[Anonymous], 1996, CHEM INDOLES

[4] Gold-catalysed direct couplings of indoles and pyrroles with 1,3-dicarbonyl compounds [J].

Arcadi, A ;

Alfonsi, M ;

Bianchi, G ;

D'Anniballe, G ;

Marinelli, F .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (03) :331-338

[5] Sequential one-pot InBr3-catalyzed 1,4-then 1,2-nucleophilic addition to enones [J].

Bandini, M ;

Cozzi, PG ;

Giacomini, M ;

Melchiorre, P ;

Selva, S ;

Umani-Ronchi, A .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3700-3704

[6] The Michael addition of indoles to α,β-unsaturated ketones catalyzed by CeCl3•7H2O-NaI combination supported on silica gel [J].

Bartoli, G ;

Bartolacci, M ;

Bosco, M ;

Foglia, G ;

Giuliani, A ;

Marcantoni, E ;

Sambri, L ;

Torregiani, E .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4594-4597

[7]

BARTOLI G, 2010, CHEM SOC REV, V39, P4449, DOI DOI 10.1039/B923063G

[8] Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].

Cacchi, S ;

Fabrizi, G .

CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920

[9] Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones [J].

Chen, DP ;

Yu, LB ;

Wang, PG .

TETRAHEDRON LETTERS, 1996, 37 (26) :4467-4470

[10] Molecular Iodine-Catalyzed Mild and Effective Synthesis of -Enaminones at Room Temperature [J].

Datta, Bandita ;

Reddy, M. B. Madhusudana ;

Pasha, M. A. .

SYNTHETIC COMMUNICATIONS, 2011, 41 (15) :2331-2336

← 1 2 3 4 5 →