3-acetoxy-flavanones and their production

Abstract

Abstract THIS DISCLOSURE CONCERNS COMPOUNDS OF THE GENERAL FORMULA: 2-R4-(1,4-PHENYLENE)-,3-R3,5-R1-O-,7-R2-O-CHROMAN-4-ONE WHERE R1=R2=-H, -CH3, -C2H5, R3=-OCOCH3, -OH, R4=-H, -OH, -OCH3, -OC2H5, -CI, AND ALKALI METAL SALTS THEREOF. THESE COMPOUNDS SHOW ANTI-NEPHROTOXIC PROPERTIES. THESE COMPOUNDS ARE CHARACTERIZED CHEMICALLY BY THE PRESENCE OF A HYDROXY OR ACETOXY RADICAL IN THE 3-POSITION. THE INVENTION IS ALSO CONCERNED WITH METHODS OF SYNTHESIS WHICH CONSIST SUCCESSIVELY IN CONDENSING ACETONITRILE AND PHLOROGLUCINOL OR ITS ALKOXY DERIVATIVE IN ETHER IN THE PRESENCE OF ZINC CHLORIDE TO OBTAIN TRIHYDROXY-ACETOPHENONE OR ITS ALKOXY DERIVATIVE; CONDENSING THIS PRODUCT WITH BENZALDEHYDE OR ITS PARA-HYDROXY OR ALKOXY DERIVATIVES TO OBTAIN 5,7,4''TRIHYDROXY-FLAVANONE. ALTERNATELY THE PRODUCT OBTAINED IN THE FIRST STEP CAN BE CONDENSED WITH P-CHLORO-BENZALDEHYDE TO OBTAIN 5,7-DIHYDROXY CHLOROFLAVANONE OR ITS ALKOXY DERIVATIVES. ON THE PRODUCT OBTAINED IS INTRODUCED AN ACETOXY RADICAL IN THE 3-POSITION BY MAINTAINING THIS COMPOUND BOILING UNDER REFLUX IN ETHYL ALCOHOL IN THE PRESENCE OF IODINE AND OF A METALLIC ACETATE SUCH AS AN ACETATE OF SILVER, LEAD, SODIUM OR ZINC IN ORDER TO OBTAIN 3-ACETOXY5,7,4''-TRIHYDROXY-FLAVONONE OR ITS DERIVATIVES. THE PRODUCT OBTAINED IS SAPONIFIED WITH DILUTE SODIUM TO OBTAIN 3,5,7,4''-TETRA-HYDROXY-FLAVNONE OR ITS DERIVATIVES.

Inventors

• 👤 Bernard Majoie

Bibliographic Details