Indirect Electrochemical N-Dimethoxyphenylation of 3-Nitro-1,2,4-triazole and Tetrazole

Using the obtaining of 1,4-dimethoxy-2-(3-nitro-1,2,4-triazole-1-yl)benzene (I) and 1,4-dimethoxy-2-(tetrazolyl-1+-2)benzene (II) as an example, a method for indirect electrosynthesis of these substances is developed. In the first stage of this process, electrosynthesis of 1,1,4,4-tetramethoxycyclohexane-2,5-diene is realized by means of oxidation of 1,4-dimethoxybenezene on a platinum anode in an environment of MeOH in a diaphragmless cell. In the second, chemical interaction of this diene with 3-nitro-1,2,4-triazole and tetrazole is performed when heating a mixture of these substances for a long time at 110°C in the presence of additives of collidine. As a result, target products I and II were obtained with a good (60–90%) yield. Realization of this process opens new possibilities for producing N-arylazoles.__________Translated from Elektrokhimiya, Vol. 41, No. 8, 2005, pp. 1014–1019.Original Russian Text Copyright © 2005 by Burasov, Vakhotina, Petrosyan.