The reaction of (N-isocyanimino)triphenylphosphorane with dialkyl acetylenedicarboxylates in the presence of 1,3-diphenyl-1,3-propanedione:: a novel three-component reaction for the stereoselective synthesis of dialkyl (Z)-2-(5,7-diphenyl-1,3,4-oxadiazepin-2-yl)-2-butenedioates

被引：155

作者：

Souldozi, Ali

Ramazani, Ali

Bouslimani, Nouri

Welter, Richard

机构：

[1] Univ Zanjan, Dept Chem, Zanjan, Iran

[2] Univ Strasbourg 1, Lab DECOMET, ILB, F-67000 Strasbourg, France

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 14期

关键词：

acetylenic ester; (N-isocyanimino)triphenylphosphorane; 1,3-diphenyl-1,3-propanedione; 1,3,4-oxadiazepine; aza-Wittig reaction;

D O I：

10.1016/j.tetlet.2007.02.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of dialkyl acetylenedicarboxylates with (N-isocyanimino)triphenylphosphorane in the presence of 1,3-diphenyl-1,3-propanedione proceed smoothly at room temperature to afford dialkyl (Z)-2-(5,7-diphenyl-1,3,4-oxadiazepin-2-yl)-2-butenedioates in high yields. The stereochemistry of the final products were confirmed by single crystal X-ray structure determination. The reaction is completely stereoselective. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2617 / 2620

页数：4

共 24 条

[1] 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 [J].