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

被引：48

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

页码：6621 / 6628

页数：8

共 9 条

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Qu, Yi
Xu, Wentao
Zhang, Jingjing
Liu, Yuxiu
Li, Yongqiang
Song, Hongjian
Wang, Qingmin
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (08): : 5379 - 5389
[2] Palladium-catalyzed dearomatizative [2+2+1] carboannulation of 1,7-enynes with aryl diazonium salts and H2O: facile synthesis of spirocyclohexadienone-fused cyclopenta[c]quinolin-4(5H)-ones
Liu, Yu
Song, Ren-Jie
Li, Jin-Heng
CHEMICAL COMMUNICATIONS, 2017, 53 (61) : 8600 - 8603
[3] Nickel-catalyzed cyclization of 1,7-enynes for the selective synthesis of dihydrocyclobuta[c]quinolin-3-ones and benzo[b]azocin-2-ones
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Hu, Yuanyuan
Jin, Hongwei
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CHEMICAL COMMUNICATIONS, 2025, 61 (18) : 3760 - 3763
[5] Sulfur Incorporation: Copper-Catalyzed Cascade Cyclization of 1,7-Enynes with Metal Sulfides toward Thieno[3,4-c]quinolin-4(5H)-ones
Liu, Yu
Zhang, Jia-Ling
Song, Ren-Jie
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ORGANIC LETTERS, 2014, 16 (22) : 5838 - 5841
[6] Copper-Catalyzed Cascade Cyclization of 1,7-Enynes toward Trifluoromethyl-Substituted 1'H-Spiro[azirine-2,4'-quinolin]-2'(3'H)-ones
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Chen, Fei
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ORGANIC LETTERS, 2017, 19 (19) : 5186 - 5189
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CHEMICAL COMMUNICATIONS, 2019, 55 (47) : 6727 - 6730
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Chimichi, Stefano
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Bian, Mouwang
Dai, Lei
Zhang, Jinghang
Yu, Qiuyu
Wang, Chang
Rong, Liangce
ORGANIC LETTERS, 2021, 23 (01) : 218 - 224

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