New efficient synthesis of 1,2,4-trisubstituted imidazoles and imidazo[1,2-c] quinazolines by a tandem aza-Wittig/electrocyclic ring-closure process

被引：16
|
作者：
Nie, Yi-Bo [1 ]
Duan, Zhuan [1 ]
Ding, Ming-Wu [1 ]
机构：
[1] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China
来源：
TETRAHEDRON | 2012年 / 68卷 / 04期
基金：
中国国家自然科学基金;
关键词：
ALPHA-AZIDOVINYL KETONES; TETRASUBSTITUTED IMIDAZOLES; CONJUGATED CARBODIIMIDES; WITTIG REACTION; DERIVATIVES; CYCLIZATION; ALKALOIDS; 2-AMINOIMIDAZOLES; ENTRY;
D O I：
10.1016/j.tet.2011.12.005
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of 1,2,4-trisubstituted imidazoles 5 were synthesized efficiently by a tandem aza-Wittig/1,5-electrocyclic ring-closure reaction of vinyliminophosphoranes 3 with aldehydes. Reactions of 5s,t with triphenylphosphine produced iminophosphoranes 7. A tandem aza-Wittig reaction of iminophosphorane 7 with isocyanate generated imidazo[1,2-c]quinazolines 9 in high yields. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：965 / 971
页数：7
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