Reaction of acylketene S,N-acetals with malonyl chloride: synthesis of novel 1,5-substituted 4-hydroxy-6-methylthio-2 (1h)-pyridones and 6,8-substituted 4-hydroxy-7-methylthio-2,5-dioxo-5,6-dihydro-2h-pyrano [3,2-c] pyridines

Chakrasali, R. T. ; Ila, H. ; Junjappa, H. (1988) Reaction of acylketene S,N-acetals with malonyl chloride: synthesis of novel 1,5-substituted 4-hydroxy-6-methylthio-2 (1h)-pyridones and 6,8-substituted 4-hydroxy-7-methylthio-2,5-dioxo-5,6-dihydro-2h-pyrano [3,2-c] pyridines Synthesis, 1988 (1). pp. 87-89. ISSN 0039-7881

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Related URL: http://dx.doi.org/10.1055/s-1988-27476

Abstract

The acylketene S,N-acetals 1 react with one equivalent of malonyl chloride in the presence of triethylamine to give novel 1,5-substituted 4-hydroxy-6-methylthio-2(1H)-pyridones 3 in good yields. However, in the presence of excess of malonyl chloride (three equivalents), the reaction proceeds further to give the corresponding pyrano[3,2-c] pyridones derivatives 4 in moderate yields.

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