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Parallel Synthesis of 1,2,3-Thiadiazoles Employing a "Catch and Release" Strategy
Published: 01 November 1998 by MDPI in The 2nd International Electronic Conference on Synthetic Organic Chemistry session Combinatorial Synthesis, Parallel Synthesis and Automation
Abstract: 1,2,3-thiadiazoles were synthesized in parallel using a polymer sulfonyl hydrazide resin (PS-TsNHNH2) and employing a "catch and release" synthesis strategy. Resin capture of ketones synthesized from Weinreb amides and Grignard reagents afforded resin-bound sulfonylhydrazones. Cyclizative cleavage of supportbound sulfonylhydrazones with thionyl chloride afforded 1,2,3-thiadiazoles. Excess thionyl chloride was neutralized using liquid-liquid extraction cartridges.
Keywords: polystyrene sulfonylhydrazine resin, 1,2,3-thiadiazole, "catch and release", resin capture