The comparative reactivity of heterocyclic diazo compounds and the corresponding diazo nium salts in C azo coupling reactions was studied using imidazole, pyrazole, and triazole derivatives as examples. The reactivities of pyrazole and imidazole derived diazonium salts are much lower than those of thiadiazole and 1,2,4 triazole derived diazonium salts but higher than those of pyrrole and indole diazo compounds.

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Alkyl 3 fluoroalkyl 3 oxopropionates react with antipyrinyldiazonium chloride to form 2 antipyrinylhydrazono 3 fluoroalkyl 3 oxopropionates. The use in these reactions of hetaryldiaz onium salts, containing NH group in the α position, leads to alkyl 7 fluoroalkyl 7 hydroxy 4,7 dihydroazolo[5,1 c]triazine 6 carboxylates. 3 Amino 1H 1,2,4 triazole, 3 amino 4 ethoxycar bonyl 1H pyrazole, and 5 amino 4 ethoxycarbonyl 1H imidazole were used as the heterocyclic component.

In general, the triazolediazonium salt (XI) is more reactive than the diazolediazonium analogues. -(SADCHIKOVA*, E. V.; MOKRUSHIN, V. S.; Russ. Chem. Bull. 54 (2005) 2, p354-p365; Ural State Tech. Univ., Ekaterinburg 620002, Russia; Eng.) -Mischke 06-127