Photo-Induced Tandem Cyclizations of 3-Iodofalvones with Electron Rich Five-member Heteroarenes

【作者】 杨谦； 王锐； 韩杰； 李晨晨； 王涛； 张尊听；

【Author】 Qian Yang;Rui Wang;Jie Han;Chenchen Li;Tao 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】 Flavones are a class of natural product which could be found in many plants. They have various biological activities, including antioxidant, anti-tumor, anti-proliferative, anti-inflammatory activities and have been used in the treatment of cancer, cardiovascular disease, neurodegenerative disorders, etc. Flavones are also an important scaffold for medicinal chemistry and versatile building blocks for the construction of various heteroaromatics. Vinyl radicals were generated from 3-iodoflavones under a mercury lamp and occurred tandem cyclizations with fused heterocyclic aromatics system entailing two consecutive C-C bond formations to synthesis benzo[e]chromeno[2,3-g]indol-13(1H)-one derivatives. The reaction worked smoothly in acetonitrile without any additives such as transition metal, ligand andoxidant giving rise to a broad variety of novel polycyclic xanthone frame works in good yields under mild and environmentally reaction conditions. The described methodology provided a rapid access to polycyclic xanthones with excellent regio-selectivity under the mild, environmental friendly condition without the requirement of any catalyst or additives.更多还原

【Abstract】 Flavones are a class of natural product which could be found in many plants. They have various biological activities, including antioxidant, anti-tumor, anti-proliferative, anti-inflammatory activities and have been used in the treatment of cancer, cardiovascular disease, neurodegenerative disorders, etc. Flavones are also an important scaffold for medicinal chemistry and versatile building blocks for the construction of various heteroaromatics. Vinyl radicals were generated from 3-iodoflavones under a mercury lamp and occurred tandem cyclizations with fused heterocyclic aromatics system entailing two consecutive C-C bond formations to synthesis benzo[e]chromeno[2,3-g]indol-13(1H)-one derivatives. The reaction worked smoothly in acetonitrile without any additives such as transition metal, ligand andoxidant giving rise to a broad variety of novel polycyclic xanthone frame works in good yields under mild and environmentally reaction conditions. The described methodology provided a rapid access to polycyclic xanthones with excellent regio-selectivity under the mild, environmental friendly condition without the requirement of any catalyst or additives.更多还原