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Synthesis 1986; 1986(11): 952-956
DOI: 10.1055/s-1986-31835
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Pyridinethiones; XIII. Alkylation of 1,5-Pentenedione Enolates, New Synthons for the Preparation of 5-Substituted 2(1H)-Pyridinethiones

Jan Becher* , Carsten E. Stidsen, Fahmy M. Asaad
  • *Department of Chemistry, University of Odense, DK-5230 Odense M, Denmark
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Publication Date:
20 August 2002 (online)

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Anions 3 of 1,5-pentenediones can be alkylated to give 2-alkyl-1, 5-pentenediones 4, whose anions 5 react with isothiocyanates to yield the oxoenoles 7. These cyclize to give the new 5-substituted 2(1H)-pyridinethiones 6 in fair yields. Anions of unsymmetrical 1,5-pentenediones yields mixtures of 2(1H)-pyridinethiones 9 and 10.