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Aroxydihydropyrans

XI. Synthesis of 3,4-dihydro-2-pyranyloxy(mercapto)quinolines and their principal properties

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of vinyl ethers and vinyl Sulfides of the quinoline series with unsaturated aldehydes gives 3,4-dihydro-2-pyranyloxy(mercapto)quinolines, in the hydrogenation of which, depending on the conditions, the multiple bonds in the pyran or pyridine ring are reduced. The ionization constants of the adducts were established by potentiometry. The vinyl ethers of 6-hydroxyquinoline, 8-hydroxy-1,2,3,4-tetrahydroquinoline, and 8-(S-vinyl)mercaptoquinoline were obtained for the first time.

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Literature cited

  1. G. G. Skvortsova, M. A. Andriyankov, and S. M. Tyrina, Khim. Geterotsikl. Soedin., 1166 (1972).

  2. M. F. Shostakovskii, G. G, Skvortsova, S. M. Tyrina, and K. V. Zapunnaya, USSR Author's Certificate No. 218186; Byul. Izobr., No. 17 (1968).

  3. A. Albert, in: Physical Methods in the Chemistry of Heterocyclic Compounds, edited by A. R. Katritzky, Academic Press (1963).

  4. T. V. Kashik, B. V. Prokop'ev, G. V. Rassolova, and S. M, Ponomareva, Izv. Akad. Nauk SSSR, Ser. Khim., 1960 (1971).

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Authors and Affiliations

  1. Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, USSR

    G. G. Skvortsova, M. A. Andriyankov, Z. V. Stepanova, T. V. Kashik, S. M. Ponomareva & D. G. Kim

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  1. G. G. Skvortsova
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  2. M. A. Andriyankov
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  3. Z. V. Stepanova
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  4. T. V. Kashik
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  5. S. M. Ponomareva
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  6. D. G. Kim
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Additional information

See [1] for communication X.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 375–378, March, 1976.

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Skvortsova, G.G., Andriyankov, M.A., Stepanova, Z.V. et al. Aroxydihydropyrans. Chem Heterocycl Compd 12, 320–323 (1976). https://doi.org/10.1007/BF00479574

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  • DOI: https://doi.org/10.1007/BF00479574

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