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Synthesis 1990; 1990(2): 162-167
DOI: 10.1055/s-1990-26822
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Synthesis of Heterocyclic Ketene N,S-Acetals and Their Reactions with Esters of α,β-Unsaturated Acids

Zhi-Tang Huang* , Xian Shi
  • *Institute of Chemistry, Academia Sinica, Beijing, People's Republic of China
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Publication Date:
17 September 2002 (online)

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Ketene S,S-acetals 2 react with 2-amino-1-ethanethiol to afford the substituted 2-methylenethiazolidines 3. The structure of these products as ketene N,S-acetals is confirmed by spectroscopic data. Compounds 3a-f react with esters of α,β-unsaturated acids to give thiazolo[3,2-a] pyrid-5-one derivatives 4, 6, and 7 through an electrophilic addition and cyclocondensation sequences.