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

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Abstract

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.

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Authors and Affiliations

  1. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia

    A. V. Burasov, T. S. Vakhotina & V. A. Petrosyan

Authors
  1. A. V. Burasov
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  2. T. S. Vakhotina
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  3. V. A. Petrosyan
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Correspondence to V. A. Petrosyan.

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Translated from Elektrokhimiya, Vol. 41, No. 8, 2005, pp. 1014–1019.

Original Russian Text Copyright © 2005 by Burasov, Vakhotina, Petrosyan.

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Burasov, A.V., Vakhotina, T.S. & Petrosyan, V.A. Indirect Electrochemical N-Dimethoxyphenylation of 3-Nitro-1,2,4-triazole and Tetrazole. Russ J Electrochem 41, 903–907 (2005). https://doi.org/10.1007/s11175-005-0154-4

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  • DOI: https://doi.org/10.1007/s11175-005-0154-4

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