Dear Nasser,
To my knowledge, there is no direct conversion from flavanone to azaflavanone (replacing O with N). However, the following method is an easy procedure to make azaflavanone derivatives:
Synthesis of 1-azaflavanone.
General procedure for synthesis of PDQOs (Figure 1, 1-8, 11-19). To a suspension of sodium amide (3.29 g, 84.3 mmol) in dry tetrahydrofuran (THF) (120 ml) 2-aminoacetophenone (2.00 g, 14.8 mmol) and then benzaldehyde (1.88 g, 17.8 mmol) were added. The reaction mixture was stirred at room temperature for 30 min and then was poured into iced water. The mixture was neutralized with dilute sulfuric acid and was then extracted with dichloromethane and washed with aqueous sodium hydrogen carbonate and water. The solvent was removed under reduced pressure, and the residue was chromatographed over a silica gel [hexane/ethyl acetate (EA); 8:2] to obtain 2’-aminochalcone as a thick yellow oil. To a solution of 2’-aminochalcone (2.6 g, 11.7 mmol) in 150 ml of ethanol, 10 ml of 50% sodium acetate in water were added, and the mixture was heated to reflux under argon for 72 h. After being cooled to room temperature, the mixture was diluted with water, and extracted with dichloromethane (DCM). The organic phase was washed with saturated brine and dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the residue was chromatographed over a silica gel (hexane/EA; 9:1) to obtain the desired products as a yellow solid.
To view the full article, please use the following link:
http://ar.iiarjournals.org/content/32/7/2819.full
Hoping this will be helpful,
Rafik
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Thanks,
Rafik
dear Prof Rafik
is it possible to convert a flavanone to thiaflavanone by direct method
Dear Nasser,
No. There is no possibility for direct conversion.
Attached is a chapter that describes the synthesis of thia- and azaflavanone.
Hoping this will be helpful,
Rafik
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