Journal of Organic Chemistry p. 3042 - 3045 (1993)
Update date:2022-08-03
Topics:
Boaz, Neil W.
Fox, Kristine M.
A novel synthesis of 2,6-diaryl-4H-thiopyran-4-ones has been developed.The title compounds were prepared by two sequential thio-Claisen condensations of a dialkyl ketone and two dithioesters.The intermediate β-thioxo ketone from the first condensation was converted to the corresponding β-(methylthio)enone for both protection and reactivity purposes.Facile addition-elimination of the methylthio moiety by a β-thioxo ketone enolate generated in the second thio-Claisen condensation afforded the desired heterocycle.This new method is rapid and simple with the only requirement being moderate substituent alkaline stability.
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Doi:10.1016/S0040-4020(99)00249-5
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(1991)
