SYNTHESIS OF 1-ALKOXY-2-ALKYL-BENZIMIDAZOLES FROM 2-NITROANILINES VIA TANDEM N-ALKYLATION-CYCLIZATION-O-ALKYLATION

被引：27

作者：

GARDINER, JM ^{[1
]}

LOYNS, CR ^{[1
]}

SCHWALBE, CH ^{[1
]}

BARRETT, GC ^{[1
]}

LOWE, PR ^{[1
]}

机构：

[1] UNIV ASTON,INST PHARMACEUT SCI,DEPT PHARMACOL & BIOL SCI,BIRMINGHAM B4 7ET,W MIDLANDS,ENGLAND

来源：

TETRAHEDRON | 1995年 / 51卷 / 14期

基金：

英国医学研究理事会;

关键词：

D O I：

10.1016/0040-4020(95)00127-T

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituted 2-nitroanilines react with benzylic, allyl and alkyl halides to give 2-aryl-1-benzyloxy-, 1-allyloxy-2-vinyl- and 1-alkoxy-2-alkyl-benzimidazoles, in a one-pot cascade process involving 1-alkylation-cyclization-O-alkylation. 2-Aryl-1-benzyloxy- and 1-allyloxy-2-vinyl- derivatives are obtained in high yields (79-98%), while with simple alkyl halides, yields of the benzimidazoles are substrate dependent. An X-ray crystal structure of 2,4-dimethyl-1-ethoxybenzimidazole is presented.

引用

页码：4101 / 4110

页数：10

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