L-proline catalyzed selective synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles

被引：145

作者：

Varala, Ravi ^{[1
]}

Nasreen, Aayesha ^{[1
]}

Enugala, Ramu ^{[1
]}

Adapa, Srinivas R. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 01期

关键词：

D O I：

10.1016/j.tetlet.2006.11.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

L-Proline (10 mol %) was found to be a versatile organocatalyst for the selective synthesis of 2-aryl-1-arylmethyl-1-H-benzimidazoles from a wide range of substituted o-phenylenediamines and aldehydes in moderate to excellent isolated yields (32-95%) under mild conditions using chloroform as a solvent at ambient temperature. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：69 / 72

页数：4

共 63 条

[1]

Alam MM, 2006, LETT ORG CHEM, V3, P187

[2] STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .39. SYNTHESIS OF BENZIMIDAZOLES CONTAINING A FUSED ALICYCLIC RING BY RHODIUM - CATALYZED HYDROFORMYLATION OF N-ALKENYL-1,2-DIAMINOBENZENES [J].

ANASTASIOU, D ;

CAMPI, EM ;

CHAOUK, H ;

JACKSON, WR .

TETRAHEDRON, 1992, 48 (36) :7467-7478

[3] Density functional theory study of the mechanism of the proline-catalyzed intermolecular aldol reaction [J].

Arnó, M ;

Domingo, LR .

THEORETICAL CHEMISTRY ACCOUNTS, 2002, 108 (04) :232-239

[4] Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions [J].

Bahmanyar, S ;

Houk, KN ;

Martin, HJ ;

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2475-2479

[5] The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions [J].

Bahmanyar, S ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) :12911-12912

[6] Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity [J].

Bahmanyar, S ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11273-11283

[7] An intramolecular palladium-catalysed aryl amination reaction to produce benzimidazoles [J].

Brain, CT ;

Brunton, SA .

TETRAHEDRON LETTERS, 2002, 43 (10) :1893-1895

[8]

Chi YC, 2000, SYNLETT, P591

[9] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[10] L-proline-catalyzed one-pot three-component reaction for the synthesis of β-alkoxy ketones [J].

Dodda, Rajasekhar ;

Zhao, Cong-Gui .

SYNTHESIS-STUTTGART, 2006, 19 (19) :3238-3242

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