Electrochemical N-arylation of azoles in MeOH using undivided electrolysis of their mixtures with 1,4-dimethoxybenzene
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.
Key wordsazoles 1,4-dimethoxybenzene paired electrosynthesis N-dimethoxyphenylazoles
Unable to display preview. Download preview PDF.
- 1.V. A. Chauzov, V. Z. Parchinskii, E. V. Sinel'shchikova, N. N. Parfenov, and V. A. Petrosyan, Izv. Akad. Nauk, Ser. Khim., 2002, 917 [Russ. Chem. Bull., Int. Ed., 2002, 51, 998].Google Scholar
- 2.V. A. Chauzov, V. Z. Parchinskii, E. V. Sinel'shchikova, A. V. Burasov, B. I. Ugrak, N. N. Parfenov, and V. A. Petrosyan, Izv. Akad. Nauk, Ser. Khim., 2002, 1402 [Russ. Chem. Bull., Int. Ed., 2002, 51, 1523].Google Scholar
- 3.D. R. Henton, R. L. McCreery, and J. S. Swenton, J. Org. Chem., 1980, 45, 369.Google Scholar
- 4.J. Catalan, J. L. M. Abbaud, and J. Elguero, Adv. Heterocycl. Chem., 1987, 41, 250.Google Scholar
- 5.B.-T. Groebel, E. Konz, H. Millaner, and R. Pistorius, Synthesis, 1979, 608.Google Scholar
- 6.Kai Hu, M. E. Niyazymbetov, and D. H. Evans, Tetrahedron Lett., 1995, 36, 7027.Google Scholar
- 7.R. Huttel, F. Buchele, and P. Jochum, Chem. Ber., 1955, 88, 1377.Google Scholar