Unexpected regiospecific reduction of the double bond by NaBH4 in 2-(1-methyl/1H-benzimidazole-2-yl)-3-aryl-acrylonitrile

被引：12

作者：

Dubey, P. K. ^{[1
]}

Reddy, P. V. V. Prasada ^{[1
]}

机构：

[1] JNT Univ, Coll Engn, Dept Chem, Hyderabad 500072, Andhra Pradesh, India

来源：

SYNTHETIC COMMUNICATIONS | 2007年 / 37卷 / 13期

关键词：

2-cyanomethyl benzimidazoles; aromatic aldehydes; NaBH4; regiospecific reduction; H-2/Pd-C; alkylations;

D O I：

10.1080/00397910701397177

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation of (1H-benzimidazole-2-yl)-acetonitrile 1 with aromatic aldehydes in 5% NaOH solution gave the corresponding 2-(1H-benzimidazole-2-yl)3-aryl-acrylonitrile 2, which on treatment with NaBH4 in ethanol unexpectedly gave 2-(1H-benzimidazole-2-yl)-3-aryl-propionitrile 3 by the regiospecific reduction of the double bond. Shaking a solution of 2 with H-2/Pd-C in methanol also gave 3. Reaction of 2 with DMS gave the corresponding N-methylated analogue 5, which also with NaBH4 gave 6, once again by the regiospecific reduction of the double bond as in the case of 1-demethylated analogue ( i. e., 2).

引用

页码：2259 / 2266

页数：8

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