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ChemInform Abstract

Reaction of aroyl chlorides (II) with KSeCN (I) generates aroyl isoselenocyanates in situ, which undergo 1,3-dipolar cycloaddition to diazoacetate (III) to provide, after a second acylation reaction, 1,2,3-selenadiazoles (IV) in moderate yields. Oligomers of the isoselenocyanates are obtained as side products. Their amount can be reduced by slow addition of aroyl chlorides, which generate low concentrations of transient isoselenocyanates. Deacylation of compounds (IV) is achieved on reaction with equimolar amounts of morpholine. Interestingly, among the oligomers one can be isolated which on reaction with morpholine produces N-aroylselenourea derivatives (VI).