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
收藏
页码：3410 / 3413
页数：4
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