Advertisement

Chemistry of Heterocyclic Compounds

, Volume 3, Issue 2, pp 478–480 | Cite as

Researches on pyranes, their analogs, and related compounds

XXI. Some acyl derivatives of chromones
  • V. A. Zagorevskii
  • Sh. M. Glozman
  • S. M. Klyuev
Article

Abstract

Condensation of 2, 4-diacetylphenol with diethyl oxalate serves as a basis for preparing 2-carbethoxy- and 2-carboxy-6-acetylchromones (I, II), 2-carbethoxy-6-ethoxyoxalyacetylchromone (V), and 2-carboxy-6-hydroxyoxalylacetylchromone (VI). The Mannich reaction is used to synthesize 6-(ω-dialkylaminopropionyl)-2-carboxychromones (VII, VIII) from compound I. Reaction of chromone-2-carbonyl chloride with enamines prepared from cyclohexanone and tetrahydrothiopyrone-4- gives syntheses of 2-(chromonoyl-2)cyclohexanone (III) and 3-(chromonoyl-2)tetrahydrothiopyrone-4 (IV). Hydrazine hydrate and compound III give the pyrazole derivative IX, while hydrazine hydrate and compound IV give pyrazole derivative X along with pyrazolylpyrazole derivative XI, which results from a second molecule of hydrazine hydrate opening the chromone ring.

Keywords

EtOH Pyrazole Hydrazine Hydrate Chromone Mannich Reaction 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    P. F. Wiley, J. Am. Chem. Soc., 74, 4326, 1952.CrossRefGoogle Scholar
  2. 2.
    P. Da Re, Farmaco, 11, 662, 1956.Google Scholar
  3. 3.
    D. V. Joshi, J. R. Merchant, and R. C. Shah, J. Org. Chem., 21, 1104, 1956.CrossRefGoogle Scholar
  4. 4.
    V. A. Zagorevskii and D. A. Zykov, ZhOKh, 30, 3679, 1960.Google Scholar
  5. 5.
    V. A. Zagorevskii, D. A. Zykov, and E. K. Orlova, ZhOKh, 34, 539, 1964.Google Scholar
  6. 6.
    V. A. Zagorevskii, I. D. Tsvetkova, E. K. Orlova, and D. A. Zykov, ZhOrKh, 1, 1517, 1965.Google Scholar
  7. 7.
    J. Schmutz, R. Hirt, and H. Zauener, Helv. chim. Acta. 35, 1168, 1952.CrossRefGoogle Scholar
  8. 8.
    V. A. Zagorevskii, D. A. Zykov, and E. K. Orlova, ZhOKh, 31, 568, 1961.Google Scholar
  9. 9.
    B. Ganguly and P. Baghi, J. Org. Chem., 21, 1415, 1956.CrossRefGoogle Scholar
  10. 10.
    L. N. Kakurina, N. F. Kucherova, and V. A. Zagorevskii, ZhOrKh, 1, 1108, 1965.Google Scholar
  11. 11.
    V. A. Zagorevskii, Sh. M. Blozman, and S. M. Klyuev, ZhOrKh, 2, 2222, 1966.Google Scholar

Copyright information

© The Faraday Press, Inc. 1969

Authors and Affiliations

  • V. A. Zagorevskii
    • 1
  • Sh. M. Glozman
    • 1
  • S. M. Klyuev
    • 1
  1. 1.Institute of Pharmacology and ChemotherapyAcademy of Medical Sciences USSRMoscow

Personalised recommendations