Deaminative Cyclization of Tertiary Amines for the Synthesis of 2-Arylquinoline Derivatives with a Nonsubstituted Vinylene Fragment

被引：15

作者：

Gao, Qinghe ^{[1
]}

Guo, Yimei ^{[1
]}

Sun, Zhenhua ^{[1
]}

He, Xiaodan ^{[2
]}

Gao, Yiqiao ^{[1
]}

Fan, Guangping ^{[1
]}

Cao, Penghui ^{[1
]}

Fang, Lizhen ^{[1
]}

Bai, Suping ^{[1
]}

Jia, Yanlong ^{[1
]}

机构：

[1] Xinxiang Med Univ, Sch Pharm, Xinxiang 453003, Henan, Peoples R China

[2] Xinxiang Med Univ, Affiliated Hosp 2, Xinxiang 453002, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2022年

基金：

中国国家自然科学基金;

关键词：

H OXIDATIVE ANNULATION; METAL-FREE SYNTHESIS; CASCADE REACTION; QUINOLINES; ANILINES; ALCOHOLS; STRATEGY; KETONES;

D O I：

10.1021/acs.orglett.2c03904

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

With triethylamine as a vinylene source, a convenient protocol for the regioselective synthesis of beta,gamma-nonsubstituted 2-arylquinolines from aldehydes and arylamines has been accomplished. The deaminative cyclization is also extended to long-chain tertiary alkylamines, enabling diverse alkyl groups to be concurrently installed into the pyridine rings. This process demonstrates a new conversion pathway for the simultaneous dual C(sp(3))-H bond functionalization of tertiary amines, wherein the transient acyclic enamines generated in situ undergo the Povarov reaction.

引用

页码：109 / 114

页数：6

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