Title: Annulation of heterocyclic secondary enamines with dicarboxylic acid dichlorides, an unexpected ring size effect
Abstract: Abstract Under very mild conditions heterocyclic secondary enamines react efficiently with malonyl chloride to produce hydroxylated 2-pyridinone-fused heterocycles. The reactions of enamines with oxalyl chloride, however, afford varied products depending upon the heterocyclic structure of the enamine. Whilst a C -acylated enamine and a lactam-fused heterocycle were obtained from the reaction of the five- and seven-membered heterocyclic enamines, respectively, the six-membered heterocyclic enamine gave 2-oxo-5,6,7,8-tetrahydro-2 H -pyrido[3,2- b ]pyran. The reaction mechanisms are discussed.
Publication Year: 2001
Publication Date: 2001-02-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 11
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