Abstract
Rearrangement to form salts of substituted 1,2,3,4-tetrahydropyrimido[1,2-a]indoles occurs during the action of POCl3, PCl3, or PBr3 on 1-aryl-2-acylpyrazolidines that have a methylene group in the α position of the acyl fragment. The resulting salts are readily converted to 10-hydroxy-2,3,4,10-tetrahydropyrimido[1,2-a]indoles by decomposition with aqueous alkali. The structures were proved by chemical transformations, UV, IR, PMR, and mass spectra, and alternative synthesis.
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V. A. Budylin, A. N. Kost, and E. D. Matveeva, Khim. Geterotsikl. Soedin., 55 (1971).
G. A. Golubeva, Yu. N. Portnov, A. N. Kost, and L. A. Sviridova, Khim. Geterotsikl. Soedin., 118 (1971).
A. N. Kost, L. A. Sviridova, G. A. Golubeva, and Yu. N. Portnov, Khim. Geterotsikl. Soedin., 371 (1970).
M. Bredereck and K. Bredereck, Chem. Ber., 94, 2278 (1961).
Yu. A. Naumov, A. N. Kost, and I. I. Grandberg, Vestnik MGU, Ser. Khim., No. 1, 46 (1965).
I. Kerble and K. Hoffmann, Helv. Chim. Acta, 39, 116 (1956).
R. S. Sagitullin, V. I. Gorbunov, A. N. Kost, N. B. Kupletskaya, and V. V. Chistyakov, Khim. Geterotsikl. Soedin., 364 (1970).
L. G. Yudin, V. A. Budylin, A. N. Kost, and V. I. Minkin, Dokl. Akad. Nauk SSSR, 176, 1096 (1967).
M. Nakagawa and T. Hino, Tetrahedron, 26, 4491 (1970).
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See [1] for communication XXIX.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 61–67, January, 1972.
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Portnov, Y.N., Golubeva, G.A. & Kost, A.N. Indole chemistry. Chem Heterocycl Compd 8, 57–62 (1972). https://doi.org/10.1007/BF00478492
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DOI: https://doi.org/10.1007/BF00478492