Oxidative cyclization of azo-coupling products of  3-substituted tropolone with bromine

Abstract

This paper reports a new method for synthesizing heterocycle-fused troponoid compounds by oxidizing azo-coupling products of 3- isopropenyltropolone and 3-cinnamoyltropolone with bromine in the presence of pyridine. Reactions of azo-couping products of 3- isopropenyltropolone (1a-1f) and 3-cinnamoyltropolone (3a-3d) with excess bromine afford 5-substitutedpenylazo-7-bromo-3-methyl-8- hydrocyclohepta [b] furan-8-one (2a-2f), 6-substituted phenylazo-2- phenyl-8-bromo-4, 9-dihydrohepta [b] pyran-4, 9-dione (4a-4d) respectively.

Key words: OXIDATION, BROMINATION, AZO COMPOUNDS

CLC Number:

O621

Cite this article

Gao Wentao;Yang Jinzong. Oxidative cyclization of azo-coupling products of 3-substituted tropolone with bromine[J]. Chin. J. Org. Chem., 1999, 19(4): 405-408.

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Oxidative cyclization of azo-coupling products of 3-substituted tropolone with bromine

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