Phosphine-Mediated Morita-Baylis-Hillman-Type/Wittig Cascade: Access to E-Configured 3-Styryl- and 3-(Benzopyrrole/furan-2-yl) Quinolinones

被引：4

作者：

Zheng, Yu ^{[1
]}

Wang, Zhi-Wei ^{[1
]}

Cheng, Wen-Shuo ^{[1
]}

Xie, Zhen-Zhen ^{[1
]}

He, Xian-Chen ^{[1
]}

Chen, Yan-Shan ^{[1
]}

Chen, Kai ^{[1
]}

Xiang, Hao-Yue ^{[1
,2
]}

Chen, Xiao-Qing ^{[1
]}

Yang, Hua ^{[1
]}

机构：

[1] Cent South Univ, Coll Chem & Chem Engn, Changsha 410083, Peoples R China

[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 02期

基金：

中国国家自然科学基金;

关键词：

DOMINO SEQUENCE; DERIVATIVES; CONSTRUCTION; OLEFINATION; CHEMISTRY; COUMARINS;

D O I：

10.1021/acs.joc.1c02149

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 I-2/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.

引用

页码：974 / 984

页数：11