SYNTHESIS OF BETA-(TRIFLUOROMETHYL)PYRROLES VIA THE CYCLOADDITION OF MUNCHNONES TO ELECTRON-DEFICIENT TRIFLUOROMETHYLATED OLEFINS

被引：22

作者：

OKANO, T ^{[1
]}

UEKAWA, T ^{[1
]}

MORISHIMA, N ^{[1
]}

EGUCHI, S ^{[1
]}

机构：

[1] NAGOYA UNIV,FAC ENGN,INST APPL ORGAN CHEM,CHIKUSA KU,NAGOYA 46401,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 18期

关键词：

D O I：

10.1021/jo00018a011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,3-dipolar cycloaddition of munchnones (1,3-oxazolium 5-olates) to beta-chloro-beta-(trifluoromethyl)vinyl phenyl ketone (1) and butyl beta-chloro-gamma,gamma,gamma-trifluorocrotonate (2) gave (trifluoromethyl)pyrroles. The monocyclic munchnones 3a-c yielded the beta-(trifluoromethyl)pyrroles 7a-c and 8a-c regiospecifically. The bicyclic and tricyclic munchnones 9a,b and 16a,b reacted with 1 and 2 to give mixtures of regioisomeric fused-ring trifluoromethylated pyrroles. In all instances, the unsaturated phenone 1 was more reactive than the crotonate 2. The cycloaddition of munchnones to the former occurred with a higher degree of regioselectivity.

引用

页码：5259 / 5262

页数：4

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