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Paper | Regular issue | Vol 75, No. 3, 2008, pp.571-576
Published online, 4th December, 2007
DOI: 10.3987/COM-07-11236
Reaction of 1,3-Oxathiin-6-ones with Bases: Synthesis of 4-Mercapto-2-pyrone

Kentaro Okuma* and Masahiro Koda

*Department of Chemistry, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

The reaction of 4-aryl-1,3-oxathiin-6-one 3,3-dioxide 3c with secondary amine gave cinnamamides 6 and ammonium sulfinates 7. On the other hand, the reaction of 4-methyl-1,3-oxathiin-6-one 1b with LDA, followed by the addition of benzoyl chloride, gave corresponding phenacyldioxenone 8a and 5-benzoyl-4-methyl-1,3-thiodioxenone 9 in nearly 1:1 ratio, whereas the reaction with 1-benzoyl-1,2,3-benzotriazole gave only 8a in 78% yield. Thermolysis of 8a gave the corresponding 4-mercapto-2-pyrone 4a in 62% yield.