Direct Oxidative Annulation of 2,3-diphenyl-4H-chromen-4-one via the UV Irradiation

【作者】 康扬； 王涛； 张洋洋； 王锐； 张尊听；

【Author】 Yang Kang;Tao Wang;Yangyang Zhang;Rui Wang;Zunting Zhang;School of Chemistry and Chemical Engineering, Shaanxi Normal University;

【机构】 School of Chemistry and Chemical Engineering, Shaanxi Normal University；

【摘要】 Chromones is a representative of the core structures of flavonoids, isoflavonoids and extensive use of biologically active compounds and drug molecules. Owing to their tremendous significance in biological and pharmaceutical activities, there has been interested in the development of various synthetic methods to obtain the derivatives of chromones. In recent years, the transition metal catalyzed involving C–H activation and annulation methods have frequently used to synthesis various important polycyclic derivatives of chromones. For example, the Palladium-catalyzed for the synthesis of fused polycyclic aromatic via aryl halides and aryne annulation or Co（I）-diphosphine-catalyzed C–H activation and annulation reactions of salicylaldehydes and alkynes have been reported to afford dibenzo[a,c]xanthen analogues. Herein, a mild and efficient transition-metal-free photo-induced intra-cyclization dehygrogenative of 2,3-diphenyl-4 H-chromen-4-one in EtOH-H₂O（19:1, v/v） at room temperature is described. This reaction provides a simple method for the synthesis of functionalized dibenzo[a,c]xanthen derivatives via photochemcial reaction. The advantages of this method were that the reaction conditions is mild and it had an easy work-up, without the emplyment of any catalysts and additives.更多还原

【Abstract】 Chromones is a representative of the core structures of flavonoids, isoflavonoids and extensive use of biologically active compounds and drug molecules. Owing to their tremendous significance in biological and pharmaceutical activities, there has been interested in the development of various synthetic methods to obtain the derivatives of chromones. In recent years, the transition metal catalyzed involving C–H activation and annulation methods have frequently used to synthesis various important polycyclic derivatives of chromones. For example, the Palladium-catalyzed for the synthesis of fused polycyclic aromatic via aryl halides and aryne annulation or Co（I）-diphosphine-catalyzed C–H activation and annulation reactions of salicylaldehydes and alkynes have been reported to afford dibenzo[a,c]xanthen analogues. Herein, a mild and efficient transition-metal-free photo-induced intra-cyclization dehygrogenative of 2,3-diphenyl-4 H-chromen-4-one in EtOH-H₂O（19:1, v/v） at room temperature is described. This reaction provides a simple method for the synthesis of functionalized dibenzo[a,c]xanthen derivatives via photochemcial reaction. The advantages of this method were that the reaction conditions is mild and it had an easy work-up, without the emplyment of any catalysts and additives.更多还原