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An unusual base-mediated ring contraction reaction of benzopyrans to benzofurans

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
33
Issue
8
Identifiers
DOI: 10.1016/s0040-4039(00)91873-2
Keywords
  • Benzopyran
  • Benzofuran
  • Ring Contraction
  • Pyrrole
  • Cromakalim

Abstract

Abstract The reaction of electron deficient pyrroles and pyrazoles with trans-3-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol under basic conditions results in the formation of 2-isopropylbenzofurans by a mechanism which appears to be dependent on the rate of the competitive dehydration reaction leading to the corresponding benzopyrans.

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