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词条 Kostanecki acylation
释义

  1. Mechanism

  2. Examples

  3. See also

  4. References

{{Use dmy dates|date=June 2013}}

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]

  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

See also

  • Allan–Robinson reaction
  • Baker–Venkataraman rearrangement

References

1. ^{{Cite journal | doi = 10.1021/cr400265z| pmid = 24555663| title = Chromone: A Valid Scaffold in Medicinal Chemistry| journal = Chemical Reviews| volume = 114| issue = 9| pages = 4960–92| year = 2014| last1 = Gaspar | first1 = A. | last2 = Matos | first2 = M. J. O. | last3 = Garrido | first3 = J. | last4 = Uriarte | first4 = E. | last5 = Borges | first5 = F. }}
2. ^{{Cite journal | doi = 10.1021/cr60113a001| title = The Chemistry of Coumarins| journal = Chemical Reviews| volume = 36| pages = 1–62| year = 1945| last1 = Sethna | first1 = S. M. | last2 = Shah | first2 = N. M. }}
3. ^{{cite journal|doi=10.1002/cber.19010340119|title=Ueber eine Bildungsweise von Chromonderivaten|year=1901|last1=v. Kostanecki|first1=St.|last2=Różycki|first2=A.|journal=Berichte der Deutschen Chemischen Gesellschaft|volume=34|pages=102–109}}
4. ^{{cite journal|author1=Mamedov, V. A. |author2=Kalinin, A. A. |author3=Gubaidullin, A. T. |author4=Litvinov, I. A. |doi=10.1023/A:1023028927007|year=2003|journal=Chemistry of Heterocyclic Compounds|volume=39|pages=96–100}}
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.

3 : Name reactions|Organic reactions|Coumarins

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