Abstract
It is shown that in the reaction of 3-nitroquinolinium salts with aliphatic ketones and amines the ketone adds to the 2 and 4 positions with the formation of tricyclic adducts — benzazabicyclononane derivatives. Their conformational analysis was carried out on the basis of the NMR spectral data. Intermediate products of the monoaddition of ketones in the 4 position of the heteroring were isolated for the unsubstituted 3-nitroquinolinium salt.
Similar content being viewed by others
Literature Cited
M. A. Yurovskaya, A. Z. Afanas'ev, V. A. Chertkov, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 9, 1213 (1988).
T. Severin, D. BÄtz, and H. Lerche, Chem. Ber., 102, 2163 (1969).
C. A. Fyfe, Tetrahedron Lett., No. 6, 659 (1968).
R. Bard, M. J. Strauss, and S. A. Topolosky, J. Org. Chem., 42, 2589 (1977).
T. Severin, D. BÄtz, and H. Lerche, Chem. Ber., 101, 2731 (1968).
F. Popp and P. Schuyler, J. Chem. Soc., No. 1, 522 (1964).
I. A. Krasavin, B. V. Parusnikov, and Yu. P. Radin, Methods for Obtaining Chemical Reagents and Preparations [in Russian], No. 23, All-Union Scientific-Research Institute of Chemical Reagents and Ultrapure Chemical Substances (1971), p. 95.
A. A. Prokopov and L. N. Yakhontov, Khim. Geterotsikl. Soedin., No. 11, 1531 (1977).
T. V. Stupnikova, B. P. Zemskii, R. S. Sagitullin, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 3, 291 (1982).
N. M. Sergeev, NMR Spectroscopy [in Russian], Izd. Moskovsk. Gosudarstv. Univ., Moscow (1981), p. 90.
L. L. Vasil'eva and K. K. Pivnitskii, Summaries of Papers Presented at the International Symposium on Chromatography in Biology and Medicine [in Russian], Moscow (1986), p. 200.
A. Bothner-By, Adv. Magn. Reson., 1, 195 (1965).
A. Bax and R. Freeman, J. Am. Chem. Soc., 104, 1099 (1982).
V. A. Chertkov and N. M. Sergeev, J. Am. Chem. Soc., 99, 6750 (1977).
O. A. Subbotin and N. M. Sergeev, J. Chem. Soc., Chem. Commun., No. 4, 141 (1976).
M. Barfield, A. M. Cohen, C. J. Fluck, R. J. Speak, S. Sternhell, and P. W. Westerman, J. An. Chem. Soc., 97, 1482 (1975).
G. B. Bryant, D. E. Welton, L. J. Glenn, and E. C. John, J. Am. Chem. Soc., 69, 365 (1947).
H. E. Baumgarten and R. P. Barkley, J. Heterocycl. Chem., 18, 925 (1981).
Author information
Authors and Affiliations
Additional information
See [1] for Communication 5.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1385–1393, October, 1988.
Rights and permissions
About this article
Cite this article
Yurovskaya, M.A., Afanas'ev, A.Z., Chertkov, V.A. et al. Synthesis of indoles from pyridinium salts. 6. Reaction of 3-nitroquinolinium salts with ketones in the presence of amines. Chem Heterocycl Compd 24, 1149–1157 (1988). https://doi.org/10.1007/BF00475693
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00475693