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

doi:10.1246/BCSJ.65.61

Paper

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

Published Jan 1, 1992 · Tomoshige Kobayashi, K. Ono, H. Kato

Bulletin of the Chemical Society of Japan

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Abstract

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.

Study Snapshot

This study demonstrates 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, with potential applications in organic

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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

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