Reaction between tert-butyl isocyanide, dialkyl acetylenedicarboxylates, and aromatic carboxylic acids:: an efficient method for the synthesis of dialkyl (E)-2{[benzoyl(tert-butyl)amino]carbonyl}-2-butenedioate derivatives

被引：58

作者：

Alizadeh, Abdolah ^{[1
]}

Rostamnia, Sadegh

Zhu, Long-Guan

机构：

[1] Tarbiat Modares Univ, Dept Chem, POB 14155-175, Tehran, Iran

[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China

来源：

TETRAHEDRON | 2006年 / 62卷 / 24期

关键词：

alkyl isocyanide; dialkyl acetylenedicarboxylate; aromatic carboxylic acid; multicomponent reaction;

D O I：

10.1016/j.tet.2006.03.102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Protonation of the reactive intermediates produced in the reaction between tert-butyl isocyanide and dialkyl acetylenedi-carboxylates by aromatic carboxylic acids leads to vinylnitrilium cations, which undergo nucteophilic reaction with conjugate bases of the carboxylic acids to produce dialkyl (E)-2-[(benzoyloxy)(tert-butylimino)methyl]-2-butenedioates and this intermediate rearranges to the dialkyl (E)-2-{[benzoyl(tert-butyl)amino]carbonyl}-2-butenedioate derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5641 / 5644

页数：4

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