Abstract
Aryl(3-bromo-2-methoxypropyl)ketones have been obtained by bromination of allylarylketones using N-bromosuccinimide. When treated with primary amines, good yields of 1-alkyl-2-arylpyrroles were obtained via 1,3-dehydrobromination and subsequent opening of the tricyclic ring in the intermediate aryl(2-methoxycyclopropyl)ketones.
Similar content being viewed by others
Literature Cited
L. N. Sobenina, A. I. Mikhaleva, and B. A. Trofimov, Usp. Khim., 58, 275 (1989).
J. M. Patterson, Synthesis, No. 5, 281 (1976).
Yu. N. Romashin, N. Al' Mokhana, and O. G. Kulinkovich, Khim. Geterotsikl. Soedin., No. 10, 1334 (1990).
I. I. Ibragimov, A. N. Kost, M. M. Guseinov, and R. A. Gadzhily, Khim. Geterotsikl. Soedin., No. 6, 790 (1976).
I. I. Ibragimov, A. N. Kost, M. M. Guseinov, R. A. Gadzhily, V. L. Dzhafarov, and S. P. Godzhaev, Khim. Geterotsikl. Soedin., No. 10, 1434 (1973).
Yu. K. Yur'ev, Practical Studies in Organic Chemistry [in Russian], Moscow State University, No. 1/2, Moscow (1961), p. 282.
C. P. Gard, J. Am. Chem. Soc., 83, 2352 (1961).
I. I. Ibragimov, Investigations in the Synthesis of Polymeric and Monomeric Products [in Russian], Elm, Baku (1977), p. 76.
R. M. Rodebaught, Tetrahedron Lett., No. 30, 2859 (1967).
O. G. Kulinkovich, I. G. Tishchenko, and V. L. Sorokin, Zh. Org. Khim., 20, 2548 (1984).
M. T. Reetz, B. Wonderoth, and R. Urs, Chem. Ber., 118, 348 (1985).
S. Jayaraman, N. Rajn, and K. Rajagopalan, Steroids, 40, 267 (1982).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 334–336, March, 1991.
Rights and permissions
About this article
Cite this article
Sorokin, V.L., Azzuz, A.A. & Kulinovich, O.G. Synthesis of 1-alkyl-2-arylpyrroles from aryl(3-bromo-2-methoxypropyl)ketones. Chem Heterocycl Compd 27, 271–272 (1991). https://doi.org/10.1007/BF00474227
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00474227