The Journal of Organic Chemistry

Catalyzed reaction of diazodiphenylethanone and related diazo ketones with enaminones as a source of pyrroles

MN Eberlin, C Kascheres

Index: Eberlin, Marcos N.; Kascheres, Concetta Journal of Organic Chemistry, 1988 , vol. 53, # 9 p. 2084 - 2086

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Citation Number: 55

Abstract

The reaction of copper (I1)-stabilized keto carbenes (1, 7, S), derived from diazo ketones, with enaminones leads to the formation of pyrroles. The cyclic enaminones 3 react with the keto carbenes on nitrogen to form products 5, 9, 11, and/or pyrroles 6, 10, and 12. Treatment of the initially formed addition products 5, 9, and 11 with KOH in ethanol leads to formation of the corresponding pyrroles for the cyclic six-membered enaminones 3a, c but not for the ...