Preparation of 6-substituted 4-chromanones

Details Preparation of 6-substituted 4-chromanones Preparation of 6-substituted 4-chromanones

1989-08-31

1991-02-12

Chan, Nicky

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549403, 549 23, C07D31122, C07D31138, C07D33506

Patent

active

049925644

ABSTRACT:
Disclosed is a practical and efficient process for preparing 6-substituted 4-chromanones from phenolic acrylate ester compounds derivable from para-substituted phenolic or thiophenolic compounds and beta-unsubstituted acrylic acid compounds which are esterifiable therewith. The process includes effecting rearrangement of a phenolic or thiophenolic acrylate ester in the presence of a rearrangement effective amount of hydrogen fluoride to the corresponding hydroxy--or mercapto (vinyl ketone) wherein the carbonyl carbon atom of the vinyl carboxy group is directly attached to the benzene ring ortho to the hydroxy or mercapto group. Thereafter, the vinyl ketone is cyclized to the corresponding 6-substituted 4-chromanone in the presence of a cyclization-effective amount of hydrogen fluoride. The 6-substituted 4-chromanones prepared by the process are useful as intermediates for preparing pharmaceutical agents.

REFERENCES:
Offe et al., Chem. Ber., 80, pp. 458-463, 464-469, (1947).
Amakasu et al., J. Org. Chem., 31, pp. 1433-1436, (1966).
Dann et al., Ann. Chem., 587, pp. 16-34, (1954).
Tilak et al., Tetrahedron, 24, pp. 949-957, (1968).
Ellis, "Chromenes, Chromenones and Chromones", John Wiley & Sons, New York, N.Y., 1977, pp. 228-235.

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