5(4H)-oxazolones.: Part XI.: Cycloaddition reaction of oxazolones and munchnones to triphenylvinylphosphonium salts as synthetic equivalents of alkynes.

被引：18

作者：

Clerici, F ^{[1
]}

Gelmi, ML ^{[1
]}

Trimarco, P ^{[1
]}

机构：

[1] Univ Milan, Fac Farm, Ist Chim Organ, I-20133 Milan, Italy

来源：

TETRAHEDRON | 1998年 / 54卷 / 21期

关键词：

D O I：

10.1016/S0040-4020(98)00264-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

5(4H)-Oxazolones 1 and munchnones 3 are reacted with triphenylvinylphosphonium bromide 2a to give, through a cycloaddition reaction, pyrrole derivatives 4a-d and 7a-c unsubstituted at C-3 and C-4. The use of substituted vinylphosphonium salts 2b,c and dipoles 1 and 3 allows the isolation of 3-methylpyrroles 4e,f and 7d,e and 3-pyrrolecarboxylic acids 9a-c, respectively. The cycloaddition reactions proceed with high regioselectivity because of the positive interaction of phosphonium group of 2 and carbonyl group of dipoles 1 and 3. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：5763 / 5774

页数：12

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