Selective syntheses of benzoxazoles and N-(2-hydroxyaryl)pyrrolidin-2-ones from the corresponding cyclopropyl amides with PPh3/CX4

被引：21

作者：

Yang, YH ^{[1
]}

Shi, M ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2006年 / 62卷 / 10期

基金：

中国国家自然科学基金;

关键词：

cyclopropyl amide; benzoxazole; triphenylphosphine; tetrahalomethane; cyclopropane; ring-expanding reaction; ring-opening reaction; pyrrolidin-2-one;

D O I：

10.1016/j.tet.2005.11.077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzoxazoles 2 can be smoothly synthesized by treatment of starting materials of N-(2-hydroxyaryl) cyclopropyl amides 1 with PPh3/CCl4 in acetonitrile in good yields. When PPh3/CBr4/MS 4 was used in the reaction system, the corresponding ring-expanding products 3 were obtained in moderate to good yields in acetonitrile at 80 degrees C. Using DCE as a solvent in this reaction, the corresponding 2-(3-chloropropyl)benzoxazoles 5 were obtained as major products. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2420 / 2427

页数：8

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