Preparation of 6-substituted 4-chromanones

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

C - Chemistry, Metallurgy

07

D

260/328, 260/359

C07D 311/22 (2006.01) C07D 335/06 (2006.01)

Patent

CA 1273945

ABSTRACT OF THE DISCLOSURE Disclosed is a practical and efficient process for preparing 6-substituted 4-chromanones of the formula: Image from phenolic acrylate ester compounds derivable from para-substituted phenolic or thiophenolic compounds and beta-unsubstituted acrylic acid compounds which are ester- ifiable therewith. The process includes effecting rear- rangement of a phenolic or thiophenolic acrylate ester in the presence of a rearrangement effective amount of hydro- gen 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 inter- mediates for preparing related pharmaceutical agents which are aldose reductase inhibitors used in the treat- ment of diabetic complications.

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