Jump to Main Content
Palladium-Catalyzed Cascade Reaction of 2-Amino-N′-arylbenzohydrazides with Triethyl Orthobenzoates To Construct Indazolo[3,2-b]quinazolinones
- Yang, Weiguang, Qiao, Rui, Chen, Jiuxi, Huang, Xiaobo, Liu, Miaochang, Gao, Wenxia, Ding, Jinchang, Wu, Huayue
- Journal of organic chemistry 2015 v.80 no.1 pp. 482-489
- X-ray diffraction, chemistry, fluorescence
- A palladium-catalyzed sequential cyclization/C–H activation cascade reaction of 2-amino-N′-arylbenzohydrazides with triethyl orthobenzoates has been developed, providing indazolo[3,2-b]quinazolinones in good to high yields. Two key intermediates of the reaction, 2-phenyl-3-(phenylamino)quinazolinone and C–H insertion palladacycle, were isolated, and their structures were unambiguously confirmed by X-ray crystallography. This method represents an unprecedented example of a halogen-free protocol to access indazolo[3,2-b]quinazolinones. Moreover, this chemistry also provides a useful tool for the discovery of fluorescent materials.