New Heterocyclization Reactions of N′-Substituted N-(2,2-Dichloro-1-cyanoethenyl)ureas with Aliphatic Amines

The reaction of substituted 3,3-dichloroprop-2-enenitriles containing an N-methylurea or N,N-dimethylurea residue in the second position with secondary aliphatic amines gives rise to previously unknown 2,5-bis(alkylamino)-1,3-oxazole-4-carbonitriles. In the case of the reaction of N-(2,2-dichloro-1-cyanoethenyl)-N '-methylureas with benzylamines, 4,5-bis(alkylamino)-1-methyl-1H-imidazol-2(5H)-ones were obtained.

Automated summary

The reaction of substituted 3,3-dichloroprop-2-enenitriles containing N-methylurea or N,N-dimethylurea residue with secondary aliphatic amines yields novel 2,5-bis(alkylamino)-1,3-oxazole-4-carbonitriles, while the reaction of N-(2,2-dichloro-1-cyanoethenyl)-N '-methylureas with benzylamines produces 4,5-bis(alkylamino)-1-methyl-1H-imidazol-2(5H)-ones under specific conditions.