A simple synthesis of 7,4'-dihydroxy-6-methoxyisoflavone, glycitein, the third soybean isoflavone.
4-Methoxyresorcinol (3) was synthesized as the precursor for glycitein (6) synthesis by the oxidation of 3-hydroxy-4-methoxybenzaldehyde (1) to the aryl formate with H2O2 and a catalytic amount of SeO2. Glycitein (6) was synthesized by cyclization of 2,4,4'-trihydroxy-5-methoxydeoxybenzoin (5) with N,N-dimethylformamide, boron trifluoride diethyl ether, and methanesulfonyl chloride in a microwave oven.
Lang'at-Thoruwa
Caroline
C
Department of Chemistry, Kenyatta University, Nairobi, Kenya.
Song
Tong T
TT
Hu
Jiang
J
Simons
Andrean L
AL
Murphy
Patricia A
PA
D002384:Catalysis; D003500:Cyclization; D007529:Isoflavones / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010946:Plants, Medicinal / Q000737:chemistry*; D012118:Resorcinols / Q000737:chemistry; D018036:Selenium Compounds; D064588:Selenium Oxides; D013025:Glycine max / Q000737:chemistry*
C474533:4-methoxyresorcinol; D007529:Isoflavones; D012118:Resorcinols; D018036:Selenium Compounds; D064588:Selenium Oxides; C086566:glycitein