Study of basic deuterium exchange in series of 4-hydroxyisoquinoline, 3-hydroxyquinoline, and 8-hydroxyquinoline derivatives

  • V. P. Lezina
  • A. U. Stepanyants
  • L. D. Smirnov
  • N. A. Andronova
  • K. M. Dyumaev
Organic and Biological Chemistry

Conclusions

  1. 1.

    A study was made of the sequence of substitution and the exchange rate of the protons of some 3-hydroxyquinoline, 8-hydroxyquinoline, and 4-hydroxyisoquinoline derivatives.

     
  2. 2.

    The most reactive in 4-hydroxyisoquinoline is the 3 position, and in 4, 8-dihydroxyisoquinoline the 7 position of the isoquinoline ring.

     
  3. 3.

    The insertion of the annulated benzene ring in the 4, 5 position of theβ-pyridol ring increases the exchange rate of the ortho- and para-protons relative to the OH group.

     
  4. 4.

    The most reactive in the 3-hydroxy- and 2-methyl-3-hydroxyquinolines is the C4H proton, while in the 3, 5-dihydroxy- and 8-hydroxyquinolines the protons of the phenol ring are the most reactive.

     
  5. 5.

    The insertion of the annulated benzene ring in the 5,6 position of 3-hydroxypyridine changes the sequence of substitution of the protons of theβ-pyridol ring.

     

Keywords

Phenol Benzene Exchange Rate Deuterium Benzene Ring 

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Literature cited

  1. 1.
    V. P. Lezina, A. U. Stepanyants, L. D. Smirnov, and K. M. Dyumaev, Izv. Akad. Nauk SSSR, Ser. Khim., 1208 (1972).Google Scholar
  2. 2.
    P. Bellingham, C. D. Johnson, and A. R. Katritsky, J. Chem. Soc., B, 866 (1968).Google Scholar
  3. 3.
    Y. Kawazoe, M. Ohnishi, and Y. Yoshioka, Chem. Pharm., Bull. (Japan),12, 1384 (1964).Google Scholar

Copyright information

© Consultants Bureau 1973

Authors and Affiliations

  • V. P. Lezina
    • 1
  • A. U. Stepanyants
    • 1
  • L. D. Smirnov
    • 1
  • N. A. Andronova
    • 1
  • K. M. Dyumaev
    • 1
  1. 1.Institute of Chemical PhysicsAcademy of Sciences of the USSRUSSR

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