Copper-Catalyzed <i>N</i>-Arylation of Pyranoquinolinones with Boronic Acids at Room Temperature without Ligand
Wei Gao,
Fang Gao,
Haikuan Yang,
Zongde Wang,
Yaru Huang
Affiliations
Wei Gao
Jiangxi Academy of Forestry, Camphor Engineering Research Center of National Forestry and Grassland Administration, Nanchang 330032, China
Fang Gao
Yongfeng County Natural Resources Bureau, Ji’An 331500, China
Haikuan Yang
Jiangxi Academy of Forestry, Camphor Engineering Research Center of National Forestry and Grassland Administration, Nanchang 330032, China
Zongde Wang
East China Woody Fragrance and Flavor Engineering Research Center of National Forestry and Grassland Administration, College of Forestry, Jiangxi Agricultural University, Nanchang 330045, China
Yaru Huang
East China Woody Fragrance and Flavor Engineering Research Center of National Forestry and Grassland Administration, College of Forestry, Jiangxi Agricultural University, Nanchang 330045, China
Pyranoquinolinones synthesized from citral were used for Cu-catalyzed N-arylation with a wide range of arylboric acids. The reaction proceeded well with a broad substrate scope, providing a direct way to access highly functional pyranoquinolinone core structure derivatives in yields of up to 80%. Compared to citral, the compounds we obtained have a much better inhibitory effect on HeLa cervical cancer cells, and compound 3p has an IC50 value of 4.6 μM, lower than cisplatin’s 5.9 μM.
