Synthesis of sydnone compounds having alternating carbon-nitrogen chain and heterocyclic groups at the 4-position.

Entirely new type sydnones having alternating carbon-nitrogen chain groups such as 3-aryl-4-(arylcarbonimidoylcarbamoyl)sydnones, 3-aryl-4-(dimethylaminomethylenecarbamoyl)sydnones, and 4-(dimethylaminomethylenethiocarbamoyl)-3-phenylsydnone were prepared in high yields from 3-aryl-4-chloroformylsydnone, 3-aryl-4-carbamoylsydnone, and 3-phenyl-4-thiocarbamoylsydnone, respectively. The cyclization of the alternating carbon-nitrogen chain groups provided new sydnone derivatives having heterocyclic substituents such as 1,2,4-oxadiazol-5-yl, 1,2,4-triazol-3-yl, and 1,2,4-thiadiazol-5-yl groups in good yields.