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Synthesis 1988; 1988(1): 87-89
DOI: 10.1055/s-1988-27476
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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

R. T. Chakrasali* , H. Ila, H. Junjappa
  • *Department of Chemistry, North-Eastern Hill University, Shillong 793 003, Meghalaya, India
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Publication Date:
12 September 2002 (online)

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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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