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


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.


EtOH Pyrazole Hydrazine Hydrate Chromone Mannich Reaction 
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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

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