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-dimethylpyrazol-1-yl)-1-(4-R-phenylamino)-2-nitro-3,4,4-trichloro-1,3-butadienes and also 1-(benzotriazol-1-yl)-1-(4-R-phenylamino)- and 1-(3,5-dimethylpyrazol-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 chlorine in the trichlorovinyl group or of bromine in the bromodichlorovinyl group 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 (ethylenediamine and 2-aminoethanol) are used only one N-nucleophilic site of the nucleophile takes part in the reaction.