Azolyl derivatives of nitrohalobutadienes: IV. Synthesis of 4-amino derivatives of 1-azolyl-1-arylamino-2-nitrotrihalo-1,3-butadienes

Reactions of 1-(benzotriazol-1-yl)-1-(4-R-phenylamino)- and 1-(3,5-dimethyl pyrazol-1-yl)-1-(4-R-phenylamino)-2-nitro-3,4,4-trichloro-1,3-butadienes an d also 1-(benzotriazol-1-yl)-1-(4-R-phenylamino)- and 1-(3,5-dimethylpyrazo l-1-yl)-1-(4-R-phenylamino)-2-nitro-4-bromo-3,4-dichloro-1,3-butadienes (R = EtO, MeO, Me) with amines proceed with replacement of the terminal chlori ne in the trichlorovinyl group or of bromine in the bromodichlorovinyl grou p by an amine rest to yield the corresponding 1-azolyl-4-amino-1-arylamino- 2-nitro-3,4-dichloro-1,3-butadienes When binucleophilic reagents (ethylened iamine and 2-aminoethanol) are used only one N-nucleophilic site of the nuc leophile takes part in the reaction.