Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles by a Sequential Aza-Wittig/Michael/Isomerization Reaction

被引：64

作者：

Nie, Yi-Bo ^{[1
]}

Wang, Long ^{[1
]}

Ding, Ming-Wu ^{[1
]}

机构：

[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 01期

基金：

中国国家自然科学基金;

关键词：

ALPHA-AZIDOVINYL KETONES; SOLID-PHASE SYNTHESIS; EFFICIENT SYNTHESIS; TETRASUBSTITUTED-IMIDAZOLES; CRYSTAL-STRUCTURE; WITTIG REACTION; DERIVATIVES; FACILE; INHIBITORS; SERIES;

D O I：

10.1021/jo201846w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbodiimides 4, obtained from aza-Wittig reactions of iminophosphorane 3 with aryl isocyanates, reacted with secondary amines in the presence of a catalytic amount of sodium alkoxide to give 1,2,4,5-tetrasubstituted imidazoles 7 in good yields. However, 4-acylimidazoles 11 were obtained, as phenols were used in the presence of a catalytic amount of potassium carbonate due to further air oxidation of the expected products 10.

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页码：696 / 700

页数：5

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