posted on 2022-01-05, 15:38authored byYu Zheng, Zhi-Wei Wang, Wen-Shuo Cheng, Zhen-Zhen Xie, Xian-Chen He, Yan-Shan Chen, Kai Chen, Hao-Yue Xiang, Xiao-Qing Chen, Hua Yang
A phosphine-mediated,
well-designed Morita–Baylis–Hillman-type/Wittig
cascade for the rapid assembly of a quinolinone framework from benzaldehyde
derivatives is developed for the first time. By rationally combining
I2/NIS-mediated cyclization, biologically relevant 3-(benzopyrrole/furan-2-yl)
quinolinones were facilely synthesized in a one-pot process by starting
from 3-styryl-quinolinones bearing an o-hydroxy/amino
group, significantly expanding the chemical space of this privileged
skeleton. Further utility of this protocol is illustrated by successfully
performing this transformation in a catalytic manner through in situ
reduction of phosphine oxide by phenylsilane.