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Facile Synthesis and Structure of Novel 2,5-Disubstituted 1,3,4-Selenadiazoles



The reaction of hydrazide with carbonyl chloride in the presence of sodium carbonates leads to the corresponding 1,2-diacylhydrazines [1at, R1C(O)NHNHC(O)R2, R1 = aryl, R2 = aryl or alkyl] in moderate to excellent yield (57–90 %). The latter reacts with 2,4-diphenyl-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent, WR) in refluxing toluene to give a series of new 2,5-disubstituted 1,3,4-selenadiazoles (2at, 51–99 % yield). All compounds were characterized spectroscopically and six compounds were characterized crystallographically. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)