The Kostanecki acylation is a method used in

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

to form

chromone Chromone (or 1,4-benzopyrone) is a derivative of benzopyran with a substituted keto group on the pyran ring. It is an isomer of coumarin. Derivatives of chromone are collectively known as ''chromones''. Most, though not all, chromones are also ...

s or

coumarins Coumarin derivatives are derivatives of coumarin and are considered phenylpropanoids. Among the most important derivatives are the 4-hydroxycoumarins, which exhibit anticoagulant properties, a characteristic not present for coumarin itself. ...

by acylation of ''O''-hydroxyaryl ketones with aliphatic acid anhydrides, followed by cyclization. If

benzoic anhydride Benzoic anhydride is the organic compound with the formula (C6H5CO)2O. It is the acid anhydride of benzoic acid and the simplest symmetrical aromatic acid anhydride. It is a white solid. Preparation and reactions It is usually prepared by the deh ...

(or

benzoyl chloride Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula . It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring () with an acyl chloride () substituent. It is ...

) is used, a particular type of

called a

flavone Flavone is an organic compound with the formula . A white solid, flavone is a derivative of chromone with a phenyl (Ph) substituent adjacent to the ether group. The compound is of little direct practical importance, but substituted derivatives, ...

is obtained. It was named after Polish chemist

Stanisław Kostanecki Stanisław Kostanecki (born 16 April 1860 in Myszaków, now in Poland then Kingdom of Prussia – 15 November 1910 in Würzburg) was a Polish organic chemist, professor who pioneered in vegetable dye chemistry e.g. curcumin Curcumin is a ...

Mechanism

The mechanism consists of three well-differentiated reactions: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. # Phenol ''O''-acylation with formation of a tetrahedral intermediate # Intramolecular

aldol condensation An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration t ...

to cyclize and to form a hydroxydihydrochromone # Elimination of the

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

group to form the chromone (or coumarin) Kostanecki Acylation mechanism

Examples

Alvocidib Alvocidib (INN; also known as flavopiridol) is a flavonoid alkaloid CDK9 kinase inhibitor under clinical development by Tolero Pharmaceuticals for the treatment of acute myeloid leukemia. It has been studied also for the treatment of arthritis an ...

(flavopiridol) * Dimefline *

Flavoxate Flavoxate is an anticholinergic with antimuscarinic effects. Its muscle relaxant properties may be due to a direct action on the smooth muscle rather than by antagonizing muscarinic receptors. Clinical uses Flavoxate is used to treat urinary bl ...

References

{{reflist Name reactions Organic reactions Coumarins

Mechanism

Examples

See also

References