Assembly of Furazan-Fused Quinolines via an Expeditious Metal-Free [2+2+1] Radical Tandem Cyclization Process

被引：11

作者：

Deng, Guobo ^{[1
,2
,3
]}

Zhong, Ronglin ^{[1
,2
]}

Song, Jianxin ^{[3
]}

Choy, Pui Ying ^{[1
,2
]}

Kwong, Fuk Yee ^{[1
,2
]}

机构：

[1] Chinese Univ Hong Kong, State Key Lab Synthet Chem, Hong Kong, Peoples R China

[2] Chinese Univ Hong Kong, Dept Chem, Hong Kong, Peoples R China

[3] Hunan Normal Univ, Key Lab Chem Biol & Tradit Chinese Med Res, Minist Educ, Changsha 410081, Hunan, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 16期

基金：

中国国家自然科学基金;

关键词：

LIGHT-EMITTING-DIODES; ACCESS;

D O I：

10.1021/acs.orglett.1c02326

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A [2+2+1]-NO-segment-incorporating heteroannulative cascade is described. This versatile method, particularly using modular cyanoarylated ketimine substrates, allows efficient access to structurally diversified quinolines embedded with an oxadiazole core. This metal-free protocol proceeds smoothly at 30 degrees C, offers easy manipulation of substituents on the quinoline moiety, and tolerates a spectrum of functional groups. Density functional theory calculation revealed that the cyano moiety is crucial to facilitate the early cyclization step in this heteroannulation process and is different from the previously established late cyclization mechanistic interpretation.

引用

页码：6520 / 6524

页数：5

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