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Reactions of β-keto thioamides with α,β-unsaturated aldehydes. Synthesis of 6-hydroxypiperidine-2-thiones and 6H-thiopyrans
Authors:Tadeusz S Jagodziński  Jacek G So?nickiAneta Weso?owska
Institution:Department of Organic Chemistry, Technical University of Szczecin, Al. Piastów 42, PL-71065 Szczecin, Poland
Abstract:Mixtures of 3-benzoylated and 3-unsubstituted 6-hydroxypiperidine-2-thione derivatives were formed in the reaction of benzoyl(acetyl) thioacetamides with α,β-unsaturated aldehydes in refluxing ethanol in the presence of catalytic amounts of triethylamine. A mechanism for the debenzoylation was proposed. Derivatives of 6H-thiopyran were obtained when an analogous reaction was carried out in refluxing pyridine. The structures of all compounds were determined with the aid of 1D NMR (1H, 13C, 13C-DEPT-135) and 2D NMR (1H, 1H COSY, 1H, 1H NOESY, 13C, 1H COSY) spectroscopy.
Keywords:benzoyl thioacetamides  acetyl thioacetamides  6-hydroxypiperidine-2-thiones  6H-thiopyrans  8  8-dimethyl-2-phenyl-3-thioxo-2-azabicyclo[2  2  2]octan-5-one
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