Abstract
N-(Trifluoromethylsulfonyl) and N-arylsulfonyl polychloroacetaldehyde imines reacted with pyrrole, 1-alkyl-, 1-benzyl-, and 1-(4-nitrophenyl)-substituted pyrroles, and bis-pyrroles to give the corresponding 2-[1-(sulfonylamino)polychloroethyl]-1H-pyrroles or mixtures of 2- and 3-[1-(sulfonylamino)polychloroethyl]-1H-pyrroles, depending on the nature of the Schiff base and substituent on the pyrrole nitrogen atom and reaction conditions. The first synthesis of 2,5-disubstituted NH-pyrrole by reaction of pyrrole with Schiff bases was described.
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Mirskova, A.N., Drozdova, T.I., Levkovskaya, G.G., Kukharev, B.F., Kalikhman, I.D., and Voronkov, M.G., Zh. Org. Khim., 1989, vol. 25, p. 1312.
Kondrashov, E.V., Rozentsveig, I.B., and Levkovskaya, G.G., Russ. J. Org. Chem., 2007, vol. 43, p. 1747.
Levkovskaya, G.G., Drozdova, T.I., Rozentsveig, I.B., and Mirskova, A.N., Usp. Khim., 1999, vol. 68, p. 638.
Mirskova, A.N., Rudyakova, E.V., Stupina, A.G., Rozentsveig, I.B., and Albanov, A.I., Khim.-Farm. Zh., 2001, no. 6, p. 21.
Rozentsveig, I.B., Levkovskaya, G.G., Kondrashov, E.V., Evstaf’eva, I.T., and Mirskova, A.N., Russ. J. Org. Chem., 2001, vol. 37, p. 1559.
Mirskova, A.N., Levkovskaya, G.G., Drozdova, T.I., Kalikhman, I.D., and Voronkov, M.G., Zh. Org. Khim., 1982, vol. 18, p. 452.
Drozdova, T.I. and Mirskova, A.N., Russ. J. Org. Chem., 2001, vol. 37, p. 284.
Pozharskii, A.F., Anisimova, V.A., and Tsupak, E.B., Prakticheskie raboty po khimii geterotsiklov (Laboratory Works on the Chemistry of Heterocycles), Rostov-on-Don: Rostov. Gos. Univ., 1988, p. 22.
Rudyakova, E.V., Mirskova, A.N., and Levkovskaya, G.G., Russ. J. Org. Chem., 2008, vol. 44, p. 1517.
Johannsen, M., Chem. Commun., 1999, p. 2233.
Kondrashov, E.V., Rozentsveig, I.B., Levkovskaya, G.G., and Mirskova, A.N., Mendeleev Commun., 2003, vol. 13, p. 25.
Kondrashov, E.V., Cand. Sci. (Chem.) Dissertation, Irkutsk, 2005.
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Original Russian Text © E.V. Kondrashov, E.V. Rudyakova, G.N. Rozentsveig, I.B. Rozentsveig, K.A. Chernyshev, L.B. Krivdin, G.G. Levkovskaya, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 9, pp. 1379–1387.
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Kondrashov, E.V., Rudyakova, E.V., Rozentsveig, G.N. et al. C-amidoalkylation of pyrroles with N-trifluoromethylsulfonyl and N-arylsulfonyl polychloroaldehyde imines. Russ J Org Chem 45, 1365–1374 (2009). https://doi.org/10.1134/S1070428009090097
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DOI: https://doi.org/10.1134/S1070428009090097