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Reactions of Lithiated 1,2,3-Thiadiazoles: Synthesis of 4-Substituted 1,2,3-Thiadiazoles
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1985
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Lithiated 1,2,3-Thiadiazoles4-Substituted 1,2,3-Thiadiazoles 3Chemical EngineeringEngineeringHeterocyclicMethyllithium Affords 4-Lithio-5-phenyl-1,2,3-thiadiazoleOrganic ChemistryLithium DiisopropylamideChemistryHeterocycle ChemistrySynthesis MethodSynthetic Chemistry
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).