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Synthesis 1986; 1986(12): 1063-1065
DOI: 10.1055/s-1986-31878
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Lithio-ketene-S,N-acetals: New Synthesis of Multifunctionalized 2-Pyridones

Hiroki Takahata* , Kyoko Yamabe, Takao Yamazaki
  • *Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University, 2630 Sugitani, Toyama 930-01, Japan
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Publikationsdatum:
12. September 2002 (online)

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Lithioketene-S,N-acetal derived from N,N-dimethylthioacetamide reacts with aryl isocyanates to give monothiodiamides, which ware transformed into enaminonitriles by sulfide extrusion of the thioiminium salts with malononitrile. Bislithioketene-O,N-acetals, generated from the enaminonitriles with 2 equivalents n-butyllithium, react with a variety of electrophiles to afford multifunctionalized 2-pyridones.