N-Arylation of azoles with low basicity by 1,4-dimethoxybenzene during undivided electrolysis |
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| Authors: | Chauzov,V. A.,Parchinskii,V. Z.,Sinel" shchikova,E. V.,Burasov,A. V.,Ugrak,B. I.,Parfenov,N. N.,Petrosyan,V. A. |
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| Affiliation: | (1) Russian Academy of Sciences, N. D. Zelinsky Institute of Organic Chemistry, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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| Abstract: | The reactions of 1,4-dimethoxybenzene with 4-nitropyrazole, 3,4-dinitro-5-methylpyrazole, 1,2,4-triazole, 3-nitro-1,2,4-triazole, and tetrazole were studied during undivided amperostatic electrolysis on a Pt electrode in MeCN, CH2Cl2, and MeOH. The main reaction products were 2-azolyl-1,4-dimethoxybenzenes and (or) 1,4-diazolyl-1,4-dimethoxycyclohexa-2,5-dienes. In all cases except 1,2,4-triazole, N-arylation occurs only in the presence of the Alk4N+ salts of azoles or 2,4,6-trimethylpyridine as a base. The mechanism of the reactions is discussed. |
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| Keywords: | paired electrosynthesis N-arylation azoles azole anions 1,4-dimethoxybenzene |
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