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Synthesis 1985; 1985(10): 945-948
DOI: 10.1055/s-1985-31395
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Reactions of Lithiated 1,2,3-Thiadiazoles: Synthesis of 4-Substituted 1,2,3-Thiadiazoles

Edward W. Thomas* , David C. Zimmermann
  • *Atherosclerosis and Thrombosis Research, The Upjohn Company, Kalamazoo, Michigan 49 001, USA
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Publikationsdatum:
27. September 2002 (online)

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Metalation of 5-phenyl-1,2,3-thiadiazole (2) with methyllithium affords 4-lithio-5-phenyl-1,2,3-thiadiazole, which is stable and reacts with aldehydes and ketones to give 4-substituted 1,2,3-thiadiazoles 3 in excellent yields. Treatment of 4-phenyl-1,2,3-thiadiazole (1) with lithium diisopropylamide, in the presence of chlorotrimethylsilane, affords 4-phenyl-5-trimethylsilyl-1,2,3-thiadiazole (7).