Synthesis of E/Z N-(1-Chlorovinyl)formamide Using Vilsmeier-Haack Reaction

被引：2

作者：

Tang, Linlin ^{[1
]}

Wang, Jingtao ^{[1
]}

Xia, Xiaojiao ^{[1
]}

Zuo, Hua ^{[1
]}

Choi, Kyung-Min ^{[2
]}

Shin, Dong-Soo ^{[2
]}

机构：

[1] Southwest Univ, Coll Pharmaceut Sci, Chongqing 400715, Peoples R China

[2] Changwon Natl Univ, Dept Chem, Chang Won 51140, South Korea

来源：

BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2019年 / 40卷 / 03期

基金：

新加坡国家研究基金会;

关键词：

Vilsmeier-Haack reaction; N-(1-chlorovinyl)formamide; Z/E isomers; 2-phenoxyethanamide derivatives; Regioselective; ENAMIDES; FUNCTIONALIZATION; ALKENYLATION; ACTIVATION; SECONDARY; ACCESS;

D O I：

10.1002/bkcs.11673

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthesis of a variety of novel Z/E N-(1-chlorovinyl)formamides through Vilsmeier-Haack reaction starting from 2-phenoxyethanamides with POCl3/DMF has been accomplished. The reactions introduced chlorine atom to the C-alpha-position and phenoxy substitutions to the C-beta-position of N-vinylformamides, and the Z/E isomers of N-(1-chlorovinyl)formamide were isolated and characterized. In most cases, Z/E N-(1-chlorovinyl)formamides were both obtained; however, for the steric hindrance reason, the reaction starting from cyclohexylamine afforded sole Z isomer of N-(1-chloro-2-(2,4-dichlorophenoxy)vinyl)-N-cyclohexylformamide as the highly regioselective product.

引用

页码：243 / 247

页数：5

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