A novel annulation reaction of N-substituted-2-nitrosoanilines with esters of α-isocyano acids. A one-pot, two-step route to 2-benzimidazole-substituted esters of α-amino acids

被引：8

作者：

Bujok, Robert ^{[1
]}

Cmoch, Piotr ^{[1
]}

Wrobel, Zbigniew ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw 42, Poland

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 23期

关键词：

Heterocycles; Nitroso group; Isocyanides; Cyclization; 3-COMPONENT REACTION; EFFICIENT; CYCLOADDITION; CONDENSATION; INHIBITORS;

D O I：

10.1016/j.tetlet.2014.04.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A BF3-promoted cc-addition of isocyanides to both nitrogen atoms of N-aryl-2-nitrosoanilines leads to stable BF3-complexes of 3-N-hydroxy-(2-alkylimino)benzimidazole derivatives, which, after reduction with Zn in AcOH produce 1-N-ary1-2-alkylaminobenzimidazoles. This two-step annulation proceeds efficiently in a one-pot protocol with isocyanides derived from esters of alpha-amino acids. The chirality of the latter remains unaffected in the reaction. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：3410 / 3413

页数：4

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