Radical Deaminative ipso-Cyclization of 4-Methoxyanilines with 1,7-Enynes for Accessing Spirocyclohexadienone-Containing Cyclopenta[c]quinolin-4-ones

被引：49
作者：
Li, Jie [1 ]
Zhang, Wen-Wen [1 ]
Wei, Xiao-Jing [1 ]
Liu, Feng [1 ]
Hao, Wen-Juan [1 ]
Wang, Shu-Liang [1 ]
Li, Guigen [2 ,3 ]
Tu, Shu-Jiang [1 ]
Jiang, Bo [1 ]
机构：
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 221116, Peoples R China
[2] Nanjing Univ, Inst Chem & BioMed Sci, Nanjing 210093, Jiangsu, Peoples R China
[3] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 13期
关键词：
CATALYZED CASCADE CYCLIZATION; N-ACYLNITRENIUM IONS; TETHERED 1,7-ENYNES; OXIDATIVE SPIROCYCLIZATION; DIAZONIUM SALTS; DEAROMATIZATION; ALKYNES; IODOCYCLIZATION; PHENOLS; LIGHT;
D O I：
10.1021/acs.joc.7b00704
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new C-center radical-triggered bicyclization cascade of N-tethered 1,7-enynes for forming 28 examples of biologically interesting spirocyclohexadienone-containing cyclopenta[c]quinolin-4-ones with two all-carbon quaternary stereocenters has been established under mild conditions. The in situ generated diazonium salts from 4-methoxyanilines and t-BuONO are served as 4-methoxyphenyl precursors without additional oxidant, enabling 6-exo-dig cyclization/5-exo-trig ipso-cyclization to construct three new C-C bonds through metal-free dearomatization. The reaction also features broad substrate scope, annulation efficiency, and high functional group tolerance.
引用
收藏
页码：6621 / 6628
页数：8
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