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Stereochemistry of nitrogen heterocycles. 48. Synthesis, configurations, and ir spectra of 1,2-dimethyldecahydroquinoline-5-ol isomers and their acetates

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Abstract

Three isomers of 1,2-dimethyldecahydroquinolin-5-ol and their acetates with cis and trans fusion of the rings and different orientations of the hydroxy and acyloxy groups were obtained. The correlation of the frequencies of the C-O, O-H, and N+-H stretching vibrations with the configurations of these compounds was studied. The 1,2-dimethyl-cis-decahydroquinolin-5-ol isomer with a syn orientation of the amino and hydroxy groups exists in a conformation with an intramolecular hydrogen bond, the character of which is determined by the functional state of the amino group (OH...N in the base and N+-H...O in the hydrochloride). The hydrochloride of the acetate of this alcohol does not form an intramolecular N+-H...O(COCH3) bond.

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Authors and Affiliations

  1. Institute of Chemical Sciences, Academy of Sciences of the Kazakh SSR, 480100, Alma Ata

    G. S. Litvinenko, N. Yu. Kuz'mina & D. V. Sokolov

Authors
  1. G. S. Litvinenko
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  2. N. Yu. Kuz'mina
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  3. D. V. Sokolov
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Additional information

See [1] for Communication 47.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 382–388, March, 1984.

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Litvinenko, G.S., Kuz'mina, N.Y. & Sokolov, D.V. Stereochemistry of nitrogen heterocycles. 48. Synthesis, configurations, and ir spectra of 1,2-dimethyldecahydroquinoline-5-ol isomers and their acetates. Chem Heterocycl Compd 20, 309–314 (1984). https://doi.org/10.1007/BF00515646

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  • DOI: https://doi.org/10.1007/BF00515646

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