Visible light driven metal- free intramolecular cyclization: a facile synthesis of 3-position substituted 3,4-dihydroisoquinolin-1( 2H)- one+

被引：15

作者：

Zou, Shuai ^{[1
]}

Geng, Shu ^{[1
]}

Chen, Lina ^{[1
]}

Wang, Haitao ^{[1
]}

Huang, Feng ^{[1
]}

机构：

[1] State Key Lab NBC Protect Civilian, Beijing 102205, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 02期

基金：

中国国家自然科学基金;

关键词：

N-RADICAL CASCADE; PHOTOREDOX CATALYSIS; ELECTRON-TRANSFER; EOSIN Y; TRIFLUOROMETHYLATION; HYDROAMINATION; CONSTRUCTION; ALKYLATION; GENERATION; HYDRAZONES;

D O I：

10.1039/c8ob02560f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A visible-light metal-free photocatalytic synthesis of 3-position substituted 3,4-dihydroisoquinolin-1(2H)-one derivatives under mild conditions in moderate to good yields is described. EosinY Na, an organic dye, which is of low cost and has good availability, is used as the photocatalyst. A wide range of substrates are tolerated and the gram-scale reaction can also proceed smoothly. Mechanistic studies indicate that a plausible free radical process is proposed.

引用

页码：380 / 387

页数：8

共 41 条

[31] Rhodium(III)-Catalyzed C-H Activation of O-Acetyl Ketoximes/N-Methoxybenzamides toward the Synthesis of Isoquinoline/Isoquinolone-Fused Bicycles
Vijayan, Ajesh
Jumaila, Choorappulan Ummu
Radhakrishnan, Kokkuvayil Vasu
[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (11) : 1561 - 1565
[32] Study of 4-quinolone antibiotics in biological samples by short-column liquid chromatography coupled with electrospray ionization tandem mass spectrometry
Volmer, DA
Mansoori, B
Locke, SJ
[J]. ANALYTICAL CHEMISTRY, 1997, 69 (20) : 4143 - 4155
[33] Visible-Light-Promoted Radical C-H Trifluoromethylation of Free Anilines
Xie, Jin
Yuan, Xiangai
Abdukader, Ablimit
Zhu, Chengjian
Ma, Jing
[J]. ORGANIC LETTERS, 2014, 16 (06) : 1768 - 1771
[34] Visible Light Photocatalytic N-Radical-based Intramolecular Hydroamination of Benzamides
Yu Xiaoye
Zhou Fan
Chen Jiarong
Xiao Wenjing
[J]. ACTA CHIMICA SINICA, 2017, 75 (01) : 86 - 91
[35] Visible-Light-Induced Trifluoromethylation of Isonitrile-Substituted Methylenecyclopropanes: Facile Access to 6-(Trifluoromethyl)-7,8-Dihydrobenzo[k]phenanthridine Derivatives
Yuan, Yu-Chao
Liu, Hou-Lu
Hu, Xu-Bo
Wei, Yin
Shi, Min
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (37) : 13059 - 13063
[36] Photocatalytic Hydrazonyl Radical-Mediated Radical Cyclization/Allylation Cascade: Synthesis of Dihydropyrazoles and Tetrahydropyridazines
Zhao, Quan-Qing
Chen, Jun
Yan, Dong-Mei
Chen, Jia-Rong
Xiao, Wen-Jing
[J]. ORGANIC LETTERS, 2017, 19 (13) : 3620 - 3623
[37] A visible-light photocatalytic N-radical cascade of hydrazones for the synthesis of dihydropyrazole-fused benzosultams
Zhao, Quan-Qing
Hu, Xiao-Qiang
Yang, Meng-Nan
Chen, Jia-Rong
Xiao, Wen-Jing
[J]. CHEMICAL COMMUNICATIONS, 2016, 52 (86) : 12749 - 12752
[38] 6,7-Dihydroxyisoindolin-1-one and 7,8-Dihydroxy-3,4-Dihydroisoquinolin-1(2H)-one Based HIV-1 Integrase Inhibitors
Zhao, Xue Zhi
Metifiot, Mathieu
Smith, Steven J.
Maddali, Kasthuraiah
Marchand, Christophe
Hughes, Stephen H.
Pommier, Yves
Burke, Terrence R., Jr.
[J]. CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2016, 16 (04) : 435 - 440
[39] Recent advances in radical-based C-N bond formation via photo-/electrochemistry
Zhao, Yating
Xia, Wujiong
[J]. CHEMICAL SOCIETY REVIEWS, 2018, 47 (08) : 2591 - 2608
[40] Hydroxyalkylation-Initiated Radical Cyclization of N-Allylbenzamide for Direct Construction of Isoquinolinone
Zhou, Wei
Ni, Shengyang
Mei, Haibo
Han, Jianlin
Pan, Yi
[J]. ORGANIC LETTERS, 2015, 17 (11) : 2724 - 2727

← 1 2 3 4 5 →