Abstract
Indoles and pyrrole were subjected to hetarylation with imidazole and benzimidazole in the presence of aliphatic, aromatic, and heteroaromatic carboxylic acid chlorides. The resulting N,N′-diacylimidazolinyl- and N,N′-diacylbenzimidazolinylindoles were converted to 2-(3′-indolyl)-1,3-diacylimidazolium and N,N′-diacylbenzimidazolium salts by the action of trityl perchlorate.
Similar content being viewed by others
Literature cited
A. K. Sheinkman, V. A. Ivanov, N. A. Klyuev, and G. A. Mal'tseva, Zh. Org. Khim., 9, 2550 (1973).
A. K. Sheinkman, Khim. Geterotsikl. Soedin., No. 1, 3 (1974).
M. Khamana, Khim. Geterotsikl. Soedin., No. 9, 1155 (1973).
P. Wolfeden and W. Jencks, J. Am. Chem. Soc., 83, 4390 (1961).
O. Gerngross, Ber., 46, 4723 (1972).
J. Bergman, Tetrahedron Lett., No. 46, 4723 (1972).
T. V. Stupnikova, V. I. Sokolov, A. F. Pozharskii, and A. K.Sheinkman, Material from the Second Symposium on the Chemistry and Technology of Heterocyclic Compounds of Fossil Fuels [in Russian], Donetsk (1973), p. 49.
L. Bellamy, Infrared Spectra of Complex Molecules, Methuen, London (1958).
R. A. Khmel'nitskii, Khim. Geterotsikl. Soedin., No. 3, 291 (1974).
A. M. Duffield and E. Djerassi, Acta Chem. Scand., 22, 2329 (1968).
V. P. Joynt, R. R. Arndt, A. Jordaan, K. Biemann, and J. L. Occolowitz, J. Chem. Soc., B, 980 (1966).
N. A. Klyuev, R. A. Khmel'nitskii, G. A. Mal'tseva, A. K. Sheinkman, V. A. Ivanov, and B. M. Zolotarev. Khim. Geterotsikl. Soedin., No. 7, 979 (1973).
J. H. Bowil, R. G. Cooks, S. -O. Lawesson, and G. Schroll, Austral. J. Chem., 20, 1601 (1967).
A. K. Sheinkman, Yu. N. Sheinker, S. L. Portnova, and A. N. Kost, Dokl. Akad. Nauk SSSR, 157, 1416 (1964).
B. I. Khristich, G. M. Suvorova, and A. I. Simonov, Khim. Geterotsikl. Soedin., No. 10. 1398 (1974).
R. Majima and T. Shigematsu, Ber., 57, 1452 (1924).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 238–247, February, 1977.
Rights and permissions
About this article
Cite this article
Sheinkman, A.K., Stupnikova, T.V., Klyuev, N.A. et al. Imidazoles in the hetarylation reaction. Chem Heterocycl Compd 13, 190–198 (1977). https://doi.org/10.1007/BF00497876
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00497876