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
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
收藏
页码:380 / 387
页数:8
相关论文
共 41 条
  • [1] New ring systems from 1,2-benzisothiazole-1,1-dioxides and related compounds
    Abramovitch, RA
    Shinkai, I
    Mavunkel, BJ
    More, KM
    OConnor, S
    Ooi, GH
    Pennington, WT
    Srinivasan, PC
    Stowers, JR
    [J]. TETRAHEDRON, 1996, 52 (09) : 3339 - 3354
  • [2] A STEREOSELECTIVE FORMAL SYNTHESIS OF (+/-)-(GAMMA)-LYCORANE
    ANGLE, SR
    BOYCE, JP
    [J]. TETRAHEDRON LETTERS, 1995, 36 (35) : 6185 - 6188
  • [3] Visible light photoredox-controlled reactions of N-radicals and radical ions
    Chen, Jia-Rong
    Hu, Xiao-Qiang
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    [J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) : 2044 - 2056
  • [4] A novel and chemoselective synthesis of substituted 3,4-dihydroisoquinolin-1(2H)-ones from o-oxiranylmethylbenzonitrile intermediates and TBAB/NaCN
    Chen, Po-Yuan
    Chen, Hsing-Ming
    Chiang, Michael Y.
    Wang, You-Feng
    Li, Sie-Rong
    Wang, Tzu-Pin
    Wang, Eng-Chi
    [J]. TETRAHEDRON, 2012, 68 (14) : 3030 - 3036
  • [5] DBU-Promoted Cyclization of ortho-(3-Hydroxy-1-alkynyl)benzamide: Synthesis of trans-3,4-Dihydroisoquinolin-1(2H)-ones and (E)-4-(1-Alkenyl)isoquinolin-1(2H)-ones
    Chen, Wanli
    Cui, Jing
    Zhu, Yinghong
    Hu, Xianchao
    Mo, Weimin
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (03) : 1585 - 1591
  • [6] Catalytic Alkene Carboaminations Enabled by Oxidative Proton-Coupled Electron Transfer
    Choi, Gilbert J.
    Knowles, Robert R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (29) : 9226 - 9229
  • [7] A convergent synthesis of 4-substituted 1,2,3,4-tetrahydroisoquinolin-1-ones
    Cholleton, N
    Zard, SZ
    [J]. TETRAHEDRON LETTERS, 1998, 39 (40) : 7295 - 7298
  • [8] SYNTHESIS OF DERIVATIVES OF ISOINDOLE AND OF PYRAZINO[2,1-A]ISOINDOLE
    FERLAND, JM
    DEMERSON, CA
    HUMBER, LG
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (02): : 361 - 365
  • [9] Synthesis and evaluation of 3-trifluoromethyl-7-substituted-1,2,3,4-tetrahydroisoquinolines as selective inhibitors of phenylethanolamine N-methyltransferase versus the α2-adrenoceptor
    Grunewald, GL
    Caldwell, TM
    Li, QF
    Criscione, KR
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (17) : 3315 - 3323
  • [10] Rhodium(III)-Catalyzed Heterocycle Synthesis Using an Internal Oxidant: Improved Reactivity and Mechanistic Studies
    Guimond, Nicolas
    Gorelsky, Serge I.
    Fagnou, Keith
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (16) : 6449 - 6457