L-Proline catalysed multicomponent synthesis of 3-amino alkylated indoles via a Mannich-type reaction under solvent-free conditions

被引：151

作者：

Kumar, Atul ^{[1
]}

Gupta, Maneesh Kumar ^{[1
]}

Kumar, Mukesh ^{[1
]}

机构：

[1] CSIR, Cent Drug Res Inst, Med & Proc Chem Div, Lucknow, Uttar Pradesh, India

来源：

GREEN CHEMISTRY | 2012年 / 14卷 / 02期

关键词：

DIVERSITY ORIENTED SYNTHESIS; POLYHYDROQUINOLINE DERIVATIVES; ORGANIC CATALYSIS; DRUG DISCOVERY; ONE-POT; CONDENSATION REACTION; PASSERINI REACTION; KETONES; WATER; ACID;

D O I：

10.1039/c1gc16297g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient L-proline catalyzed one-pot synthesis of 3-amino-alkylated indoles has been developed via a three-component Mannich-type reaction viz. secondary amines, aldehyde and indoles under solvent-free conditions at room temperature. Several amino acids (acidic, basic and neutral) have been screened for the reaction but the best results were obtained with L-proline.

引用

页码：290 / 295

页数：6

共 70 条

[1] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].

Ahrendt, KA ;

Borths, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244

[2] Revisiting the Passerini reaction under eco-friendly reaction conditions [J].

Andrade, Carlos Kleber Z. ;

Takada, Sayuri Cristina S. ;

Suarez, Paulo Anselmo Z. ;

Alves, Melquizedeque B. .

SYNLETT, 2006, (10) :1539-1542

[3] Stereochemical control of the Passerini reaction [J].

Andreana, PR ;

Liu, CC ;

Schreiber, SL .

ORGANIC LETTERS, 2004, 6 (23) :4231-4233

[4] Multiple-component condensation strategies for combinatorial library synthesis [J].

Armstrong, RW ;

Combs, AP ;

Tempest, PA ;

Brown, SD ;

Keating, TA .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131

[5] ADDITION OF KETONES TO SCHIFF BASES [J].

BLATT, AH ;

GROSS, N .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (11) :3306-&

[6] A general organic catalyst for asymmetric addition of stabilized nucleophiles to acyl imines [J].

Bode, Christiane M. ;

Ting, Amal ;

Schaus, Scott E. .

TETRAHEDRON, 2006, 62 (49) :11499-11505

[7] Green chemistry approaches to the synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones by a three-component coupling of one-pot condensation reaction:: Comparison of ethanol, water, and solvent-free conditions [J].

Bose, DS ;

Fatima, L ;

Mereyala, HB .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :587-590

[8] Passerini Three-Component Reaction of Alcohols under Catalytic Aerobic Oxidative Conditions [J].

Brioche, Julien ;

Masson, Geraldine ;

Zhu, Jieping .

ORGANIC LETTERS, 2010, 12 (07) :1432-1435

[9] Mannich-type reaction catalyzed by silica-supported fluoroboric acid under solvent-free conditions [J].

Chen, WeiYi ;

Li, XinSheng ;

Lu, Jun .

SYNTHETIC COMMUNICATIONS, 2008, 38 (04) :546-552

[10] A novel ring-substituted diindolylmethane, 1,1-bis[3′-(5-methoxyindolyl)]-1-(p-t-butylphenyl) methane, inhibits extracellular signal-regulated kinase activation and induces apoptosis in acute myelogenous leukemia [J].

Contractor, R ;

Samudio, IJ ;

Estrov, Z ;

Harris, D ;

McCubrey, JA ;

Safe, SH ;

Andreeff, M ;

Konopleva, M .

CANCER RESEARCH, 2005, 65 (07) :2890-2898

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