Abstract
Reaction of isopropylphenyl- and isopropyl-2-thienylketoximes with acetylene, catalyzed by the system MOH (M=Na, K)-DMSO, gave 2-phenyl- and 2-(2-thienyl)-3,3-dimethyl-3H-pyrroles as well as the reaction intermediates O-vinylisopropylphenylketoxime and 2-phenyl-3,3-dimethyl-5-hydroxypyrroline. The yield of the condensation products depends on the structure of the ketoximes and the conditions for the reaction with acetylene.
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Literature Cited
M. P. Samms and A. R. Katritzky, Advances in Heterocyclic Chemistry, Academic Press, New York (1982), p. 234.
A. G. Jackson, General Organic Chemistry, Vol. 8 [Russian translation], Khimiya, Moscow (1985), p. 332.
A. Padwa and Y. Kulkarni, Tetrahedron Lett., No. 2, 107 (1979).
Y. Kawamatsu, H. Sugihare, and Y. Hamiro, Japanese Patent No. 7,416,864; Chem. Abstr., 82, 125271 (1975).
K. Fridrich, G. Bock, and H. Frits, Tetrahedron Lett., No. 36, 3327 (1978).
U. Widmer, N. Gakis, B. Arnet, H. Heimgartner, and H. Schmid, Chimia, 30, No. 10, 453 (1976).
F. D. Polyak, A. V. Eremeev, M. P. Gavars, A. P. Gaukhman, and I. B. Mazheika, Khim. Geterotsikl. Soedin., No. 7, 894 (1988).
C. Pak-Kan and M. P. Sammes, Tetrahedron Lett., 28, 2775 (1987).
I. Birtwistle and V. Rogers, J. Chem. Soc., Perkin 1, 1347 (1987).
F. Closs, R. Gompper, H. Moth, and H.-U. Wagner, Angew. Chem., 100, No. 6, 875 (1988).
A. Eddaif, A. Laurent, P. Mison, and N. Pelliser, Tetrahedron Lett., 25, 2779 (1981).
B. A. Trofimov, S. G. Shevchenko, S. E. Korostova, A. I. Mikhaleva, M. V. Sigalov, and L. B. Krivdin, Khim. Geterotsikl. Soedin., No. 1, 1566 (1990).
N. S. Prostakov, A. V. Varlamov, T. N. Borisova, and N. D. Sergeeva, Khim. Geterotsikl. Soedin., No. 9, 1286 (1987).
B. A. Trofimov, S. G. Shevchenko, S. E. Korostova, A. I. Mikhaleva, and V. V. Shcherbakov, Khim. Geterotsikl. Soedin., No. 11, 1573 (1985).
T. N. Borisova, A. V. Varlamov, N. D. Sergeeva, A. T. Soldatenkov, O. V. Zvolinski, A. A. Astakhov, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 7, 973 (1987).
S. E. Korostova, A. I. Mikhaleva, L. N. Sobenina, S. G. Shevchenko, and V. V. Shcherbakov, Khim. Geterotsikl. Soedin., No. 11, 1501 (1985).
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).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1371–1374, October, 1991.
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Korostova, S.E., Shevchenko, S.G. & Sigalov, M.V. A novel synthesis of 3H-pyrroles. Chem Heterocycl Compd 27, 1101–1104 (1991). https://doi.org/10.1007/BF00486806
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DOI: https://doi.org/10.1007/BF00486806