1. Synthesis of cis/trans-dihydrochromenones via a photoinduced rearrangement of 4-phenyl-3-aryl/cyclohexenylcoumarins
- Author
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Tao Wang, Ding Wang, Zunting Zhang, Wangxi Gao, Yong Liang, and Lixin Niu
- Subjects
chemistry.chemical_compound ,chemistry ,Transition metal ,Aryl ,Organic Chemistry ,Irradiation ,Physical and Theoretical Chemistry ,Photochemistry ,Biochemistry ,Isomerization ,Environmentally friendly ,Argon atmosphere ,Cis–trans isomerism - Abstract
A concise and environmentally friendly protocol has been developed for the synthesis of cis-dihydrochromenones and trans-dihydrochromenones in EtOH at room temperature. Irradiation of 4-phenyl-3-arylcoumarins in EtOH with 313 nm UV light under an argon atmosphere at room temperature gave cis-4b,15c-dihydro-16H-benzofuro[3',2':7,8]phenanthro[9,10-c]chromen-16-ones and cis-8c,14b-dihydro-9H-benzo[11,12]chryseno[5,6-c]chromen-9-ones in good yields. And an analogous treatment of 4-phenyl-3-alkenylcoumarins as 4-phenyl-3-arylcoumarins provided trans-1,2,3,4,4a,14b-hexahydro-5H-phenanthro[9,10-c]chromen-5-ones. The described photorearrangement proceeded smoothly without the addition of any transition metals and additives. The photorearrangement of 4-phenyl-3-arylcoumarins is believed to proceed via 6π-electrocyclization, a [1,3]-hydrogen shift and keto-enol isomerization.
- Published
- 2021
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