Arenium cation as the key intermediate of the electrosynthesis of <Emphasis Type="Italic">N</Emphasis>-(2,5-dimethoxyphenyl)azoles. A new approach to the synthesis of <Emphasis Type="Italic">N</Emphasis>-(dimethoxyphenyl)azoles |
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Authors: | V A Petrosyan A V Burasov |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | Data on the effect of the acid-base properties of the medium on the yield and composition of the products of N-dimethoxyphenylation of azoles (pyrazole, triazole, their substituted derivatives, and tetrazole) upon galvanostatic electrolysis
of azole—1,4-dimethoxybenzene mixtures in nucleophilic (MeOH) and neutral (MeCN) media were considered and the trends of this
process were discussed. The generation of arenium cations (1,4-dimethoxy-1-azolylbenzenium in MeCN and 1,1,4-trimethoxybenzenium
in MeOH) as the key intermediates of electrosynthesis of N-(dimethoxyphenyl)azoles, was proved experimentally. A new approach to the synthesis of N-(dimethoxyphenyl)azoles through electrosynthesis of 1,1,4,4-tetramethoxycyclohexa-2,5-diene by electrooxidation of 1,4-dimethoxybenzene
in MeOH as the first step and the reaction of this quinone diketal with azoles as the second step was suggested. The efficiency
of this route to N-(dimethoxyphenyl)azoles is comparable with the efficiency of the purely electrochemical one-step process.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2101–2109, November, 2007. |
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Keywords: | 1 4-dimethoxybenzene azoles electrooxidation N-(2 5-dimethoxyphenyl)azoles arenium cation 1 1 4 4-tetramethoxycyclohexa-2 5-diene |
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