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Electrochemical N-arylation of azoles in MeOH using undivided electrolysis of their mixtures with 1,4-dimethoxybenzene

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Abstract

The reactions of 1,4-dimethoxybenzene with azoles (pyrazole, triazole, and their derivatives, as well as tetrazole) were studied by undivided amperostatic electrolysis at Pt electrodes in MeOH. The process proceeds via the formation of a 1,1,4-trimethoxyarenonium cation as the key intermediate and affords 1,1,4,4-tetramethoxycyclohexa-2,5-diene, 1,1,4-trimethoxy-4-(azol-1-yl)cyclohexa-2,5-diene, and 1,4-dimethoxy-2-(azol-1-yl)benzene as the main products. Azole and solvent molecules compete as nucleophiles during electrolysis. A fine mechanism of the process was considered.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

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

Authors
  1. V. A. Petrosyan
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  2. A. V. Burasov
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  3. T. S. Vakhotina
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Dedicated to Academician N. K. Kochetkov on the occasion of his 90th birthday.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1166–1171, May, 2005.

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Petrosyan, V.A., Burasov, A.V. & Vakhotina, T.S. Electrochemical N-arylation of azoles in MeOH using undivided electrolysis of their mixtures with 1,4-dimethoxybenzene. Russ Chem Bull 54, 1197–1202 (2005). https://doi.org/10.1007/s11172-005-0380-7

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  • DOI: https://doi.org/10.1007/s11172-005-0380-7

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