A NOVEL SKELETAL REARRANGEMENT OF 2-AZABICYCLO[2.2.1]HEPT-5-ENE-3-CARBOXYLIC ACID-DERIVATIVES INTO 2-OXABICYCLO[3.3.0]OCT-7-EN-3-ONES UNDER ACIDIC CONDITIONS

被引：13

作者：

KOBAYASHI, T

ONO, K

KATO, H

机构：

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1992年 / 65卷 / 01期

关键词：

D O I：

10.1246/bcsj.65.61

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of ethyl 2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate with aroyl chloride and the subsequent hydrolysis of the ester group provided 2-aroyl-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylic acid derivatives, which underwent a stereospecific rearrangement giving 4-aroylamino-2-oxabicyclo[3.3.0]oct-7-en-3-ones by treatment with trifluoroacetic acid. On the other hand, the reaction of 2-benzoyl-2-azabicyclo[2.2.1]hept-5-ene with trifluoroacetic acid in heated benzene afforded 1-[(benzoylamino)methyl]-1,3-cyclopentadiene which afforded a Diels-Alder cycloadduct with N-phenylmaleimide. A plausible mechanism for the rearrangement is presented.

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页码：61 / 65

页数：5

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