Synthesis of Isoquinolines and Related Heterocycles under Visible-Light Conditions

被引：4

作者：

Yuan, Yurong ^{[1
]}

Faure, Clara ^{[1
]}

Menigaux, Doriane ^{[1
]}

Berthelot, Mathieu ^{[1
]}

Belmont, Philippe ^{[1
]}

Brachet, Etienne ^{[1
]}

机构：

[1] Univ Paris Cite, CNRS, UMR 8038, Fac Pharm Paris, F-75006 Paris, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 22期

关键词：

PALLADIUM-CATALYZED IMINOANNULATION; EFFICIENT SYNTHESIS; INTERNAL ALKYNES; C-H; CYCLIZATION; PYRIDINES; DERIVATIVES; OXIMES; REACTIVITY; QUINOLINES;

D O I：

10.1021/acs.joc.3c01782

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Visible-light catalysis is now widely acknowledged as a potent approach for efficiently constructing various types of frameworks, particularly bioactive compounds, with high yields. However, there is still a strong need for further advancements in these methods because certain delicate compounds cannot be synthesized due to structural sensitivity. In this context, a seamless reaction pathway toward 6-membered ring nitrogen-containing heterocycles is presented here, offering access to isoquinoline derivatives and related heterocycles.

引用

页码：15750 / 15760

页数：11

共 50 条

[1] Photocyclization of iminyl radicals:: Theoretical study and photochemical aspects
Alonso, Rafael
Campos, Pedro J.
Rodriguez, Miguel A.
Sampedro, Diego
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (06) : 2234 - 2239
[2] New light-induced iminyl radical cyclization reactions of acyloximes to isoquinolines
Alonso, Rafael
Campos, Pedro J.
Garcia, Barbara
Rodriguez, Miguel A.
[J]. ORGANIC LETTERS, 2006, 8 (16) : 3521 - 3523
[3] Visible-Light-Promoted and One-Pot Synthesis of Phenanthridines and Quinolines from Aldehydes and O-Acyl Hydroxylamine
An, Xiao-De
Yu, Shouyun
[J]. ORGANIC LETTERS, 2015, 17 (11) : 2692 - 2695
[4] STUDIES ON SRN1 REACTIONS-9 - A NEW ACCESS TO THE ISOQUINOLINE RING-SYSTEM
BEUGELMANS, R
CHASTANET, J
ROUSSI, G
[J]. TETRAHEDRON, 1984, 40 (02) : 311 - 314
[5] Bischler A., 1893, CHEM BER-RECL, V26, P1903, DOI [DOI 10.1002/CBER.189302602143, 10.1002/cber.189302602143]
[6] Visible light C-H amidation of heteroarenes with benzoyl azides
Brachet, E.
Ghosh, T.
Ghosh, I.
Koenig, B.
[J]. CHEMICAL SCIENCE, 2015, 6 (02) : 987 - 992
[7] Photocatalytic functionalizations of alkynes
Chalotra, Neha
Kumar, Jaswant
Naqvi, Tahira
Shah, Bhahwal Ali
[J]. CHEMICAL COMMUNICATIONS, 2021, 57 (86) : 11285 - 11300
[8] ANTIFUNGAL ACTIVITIES OF BISISOQUINOLINIUM AND BISQUINOLINIUM SALTS
COLLIER, HOJ
POTTER, MD
TAYLOR, EP
[J]. BRITISH JOURNAL OF PHARMACOLOGY AND CHEMOTHERAPY, 1955, 10 (03): : 343 - 348
[9] Synthesis of 3-substituted 4-aroylisoquinolines via Pd-catalyzed carbonylative cyclization of 2-(1-alkynyl)benzaldimines
Dai, GX
Larock, RC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) : 7042 - 7047
[10] Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions
Davies, Jacob
Booth, Samuel G.
Essafi, Stephanie
Dryfe, Robert A. W.
Leonori, Daniele
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) : 14017 - 14021

← 1 2 3 4 5 →