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Kostanecki acylation

Kostanecki acylation

The Kostanecki acylation is a method used in organic synthesis to form chromones or coumarins by acylation of O-hydroxyaryl ketones with aliphatic acid anhydrides, followed by cyclization. If benzoic anhydride (or benzoyl chloride) is used, a particular type of chromone called a flavone is obtained. It was named after Polish chemist Stanisław Kostanecki.

Mechanism

The mechanism consists of three well-differentiated reactions:

  1. Phenol O-acylation with formation of a tetrahedral intermediate
  2. Intramolecular aldol condensation to cyclize and to form a hydroxydihydrochromone
  3. Elimination of the hydroxyl group to form the chromone (or coumarin)

Examples

  • Alvocidib (flavopiridol)
  • Dimefline
  • Flavoxate

References

References

  1. (2014). "Chromone: A Valid Scaffold in Medicinal Chemistry". Chemical Reviews.
  2. (1945). "The Chemistry of Coumarins". Chemical Reviews.
  3. (1901). "Ueber eine Bildungsweise von Chromonderivaten". Berichte der Deutschen Chemischen Gesellschaft.
  4. (2003). "3-Benzoylquinoxalin-2(1H)-one in the Kostanecki-Robinson Reaction. Synthesis and Structure of 2-Oxo-4-phenylpyrano[2,3-b]quinoxaline". Chemistry of Heterocyclic Compounds.
  5. Ellis, G. P. (1977) ''Chromenes, Chromanones, and Chromones from The Chemistry of Heterocyclic Compounds'', Weissberger, A. and Taylor, E. C., eds.; Wiley & Sons: New York, vol. 31, p. 495.
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name-reactions organic-reactions coumarins
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