Abstract
The reaction of 1-methyl-2-acetylpyrrole oxime with acetylene at atmospheric and increased pressure can be catalyzed by KOH-DMSO superbase to give 1-methyl-2-(2-pyrrolyl)pyrrole, N-vinyl-2-[1-methyl(2-pyrrolyl)]pyrrole, and the reaction intermediate methyl-2-(1-methylpyrrolyl)-O-vinyloxime.
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S. E. Korostova, S. G. Shevchenko, and M. V. Sigalov, Khim. Geterotsikl. Soedin., No. 2, 187 (1991).
A. H. Jackson, in: General Organic Chemistry, Vol. 8, Nitrogen Heterocycles, Chemistry, N. K. Kochetkov (ed.), [Russian translation], Moscow (1985), p. 332.
D. Brown, D. Griffiths, M. E. Rider, and R. C. Smith, J. Chem. Soc., Perkin Trans. 1, No. 3, 455 (1986).
A. Gossauer, The Chemistry of Pyrrole, Springer-Verlag, Heidelberg (1974).
K. M. Smith, Chem. Soc. Quarterly Rev., 25, 31 (1971).
E. P. Vyazova, L. V. Fetisova, M. A. Azhigirova, and A. A. Khachatur'yan, Khim.-farm. Zh., No. 1, 81 (1988).
A. Watanabe, M. Tanaka, and J. Tanaka, Bull. Chem. Soc. Jpn., 54, 2278 (1981).
H. Makoto, O. Niwa, A. Sugita, and T. Tamamura, Jpn. J. Appl. Phys., 24, No. 2, 79 (1985).
O. Inganas and I. Lundstrom, J. Electrochim. Soc., 131, 1129 (1984).
D. L. Boger and M. Patel, Tetrahedron Lett., 28, 2499 (1987).
F. Heinz and F. Heinz, Monatsh. Chem., 119, 247 (1988).
T. Kauffmann and H. Lexy, Chem. Ber., 114, 3674 (1981).
D. L. Boger and M. Patel, J. Org. Chem., 53, 1405 (1988).
D. Brown, D. Griffiths, M. E. Rider, and R. C. Smith, J. Chem. Soc., Perkin Trans.1, No. 3, 455 (1986).
B. A. Trofimov and A. I. Mikhaleva, N-Vinylpyrroles [in Russian], Science, Novosibirsk (1984).
B. A. Trofimov, S. E. Korostova, A. I. Mikhaleva, L. N. Sobenina, V. V. Shcherbakov, and M. V. Sigalov, Khim. Geterotsikl. Soedin., No. 2, 276 (1983).
B. A. Trofimov, S. G. Shevchenko, S. E. Korostova, A. I. Mikhaleva, and V. V. Shcherbakov, Khim. Geterotsikl. Soedin., No. 11, 1573 (1985).
M. A. Yurovskaya, A. Z. Afanas'ev, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 8, 1077 (1984).
D. Dhanak, C. B. Reese, S. Romana, and G. Zappia, J. Chem. Soc., Chem. Commun., No. 12, 903 (1986).
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See [1] for Communication 44.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 460–463, April, 1991.
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Korostova, S.E., Shevchenko, S.G., Sigalov, M.V. et al. Pyrroles from ketoximes and acetylene. 45. A new route to 2,2-dipyrroles. Chem Heterocycl Compd 27, 363–365 (1991). https://doi.org/10.1007/BF00480830
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DOI: https://doi.org/10.1007/BF00480830