Showing papers on "Triazene published in 1972"

Synthesis and Reactions of 1-Alkyl-3-(o-carbalkoxyphenyl)-triazenes

Abstract: The reaction of diazotized anthranilate esters with primary aliphatic amines has been reinvestigated, giving rise to a new series of comparatively unstable 1-alkyl-3-(o-carbalkoxyphenyl)-triazenes (3). The structures of the products have been confirmed by spectroscopic analysis, molecular ion mass measurements, and from the results of chemical degradation. The spectroscopic properties indicate a preference for the tautomer in which the azo-group is non-conjugated with the benzene ring, Ar•NH•N=N•R; this hypothesis is partly supported by the chemical degradation. In general, the triazenes (3) break down by fragmentation of the triazene moiety to give anthranilic acid derivatives, or undergo cyclization to 3-alkyltriazinones (1). The alkyltriazinones are also obtained directly in the coupling reaction of the diazonium salt with the amine in the presence of a sodium acetate buffer. The cyclization is quantitative when catalyzed by activity V alumina; a wide variation in the product distribution obtained by r...

Triazine Intermediates in the Decomposition of 1-(o-Carbethoxyphenyl)-3-(o-cyanophenyl)-triazene in Aqueous Ethanol

Abstract: The thermal decomposition of 1-(o-carbethoxyphenyl)-3-(o-cyanophenyl)-triazene (4) in aqueous ethanol has been found to give 2-phenylquinazolin-4(3H)-one (8); the formation of triazine intermediates in the reaction has been established.