From Wikipedia, the free encyclopedia
The Kostanecki acylation is a method used in
organic synthesis to form
chromones
[1] or
coumarins
[2] by acylation of O -hydroxyaryl ketones with aliphatic acid anhydrides, followed by cyclization.
[3] If
benzoic anhydride (or
benzoyl chloride ) is used, a particular type of
chromone called a
flavone is obtained.
Mechanism
The mechanism consists of three well-differentiated reactions:
[4]
[5]
Phenol O -acylation with formation of a tetrahedral intermediate
Intramolecular
aldol condensation to cyclize and to form a hydroxydihydrochromone
Elimination of the
hydroxyl group to form the chromone (or coumarin)
Examples
See also
References
^ Gaspar, A.; Matos, M. J. O.; Garrido, J.; Uriarte, E.; Borges, F. (2014).
"Chromone: A Valid Scaffold in Medicinal Chemistry" . Chemical Reviews . 114 (9): 4960–92.
doi :
10.1021/cr400265z .
PMID
24555663 .
^ Sethna, S. M.; Shah, N. M. (1945). "The Chemistry of Coumarins". Chemical Reviews . 36 : 1–62.
doi :
10.1021/cr60113a001 .
^ v. Kostanecki, St.; Różycki, A. (1901).
"Ueber eine Bildungsweise von Chromonderivaten" . Berichte der Deutschen Chemischen Gesellschaft . 34 : 102–109.
doi :
10.1002/cber.19010340119 .
^ Mamedov, V. A.; Kalinin, A. A.; Gubaidullin, A. T.; Litvinov, I. A.; Levin, Ya. A. (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 . 39 (1): 96–100.
doi :
10.1023/A:1023028927007 .
S2CID
98794444 .
^ 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.