Photoredox Radical Cyclization of o-Vinylaryl Isocyanides and Aryldiazonium Tetrafluoroborates for the Synthesis of 2,4-Disubstituted Quinolines

被引：0

作者：

Gao, Mei-Jin ^{[1
]}

Ding, Chuan ^{[1
]}

Huang, Peng-Fei ^{[1
]}

Xie, Rong ^{[1
]}

Liu, Yu ^{[1
]}

机构：

[1] Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 90卷 / 13期

基金：

中国国家自然科学基金;

关键词：

DOEBNER-VON MILLER; BIOLOGICAL EVALUATION; EFFICIENT; DERIVATIVES; ACCESS;

D O I：

10.1021/acs.joc.4c03121

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Quinolines, a significant part of nitrogen-containing heterocycles, are widely found in functional compounds. Herin, a photochemical radical cyclization reaction of o-vinylaryl isocyanides and aryldiazonium tetrafluoroborates, has been reported to build 2,4-diaryl quinolines. Readily accessible aryl diazonium salts were utilized as aryl radical precursors at room temperature. This approach allowed good functional group tolerance and substrate applicability.

引用

页码：4571 / 4579

页数：9

共 50 条

[41] Heterogeneous gold(I)-catalyzed cyclization between ynals and amidines: An efficient and practical synthesis of 2,4-disubstituted pyrimidines
Jiang, Minhua
Nie, Quan
Cai, Mingzhong
SYNTHETIC COMMUNICATIONS, 2019, 49 (19) : 2488 - 2500
[42] [3+2] Anionic Cycloaddition of Isocyanides to Acyclic Enamines and Enaminones: A New, Simple, and Convenient Method for the Synthesis of 2,4-Disubstituted Pyrroles
Efimov, Ilya, V
Matveeva, Maria D.
Luque, Rafael
Bakulev, Vasiliy A.
Voskressensky, Leonid G.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (09) : 1108 - 1113
[43] Synthesis of 2,4-Disubstituted Oxazoles and Thiazoles via Brønsted Acid-Catalyzed Cyclization of α-diazoketones with Amides
Luo, Mengxiang
Li, Lewan
Chen, Shixin
Yan, Qiongjiao
Lv, Jian
Zeng, Jie
Wang, Haifeng
Gu, Shuangxi
Chen, Fener
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (07): : 5038 - 5048
[44] Diastereoselective synthesis of 2,4-disubstituted tetrahydropyranols and ethers via a Prins-type cyclization catalyzed by scandium triflate
Zhang, WC
Li, CJ
TETRAHEDRON, 2000, 56 (16) : 2403 - 2411
[45] Iron-Catalyzed Cyclization of Nitrones with Geminal-Substituted Vinyl Acetates: A Direct [4+2] Assembly Strategy Leading to 2,4-Disubstituted Quinolines
Zhong, Mingbing
Sun, Song
Cheng, Jiang
Shao, Ying
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (22): : 10825 - 10831
[46] Efficient synthesis of 2,4-disubstituted quinolines: calix[n]arene-catalyzed Povarov-hydrogen-transfer reaction cascade
Simoes, Juliana Baptista
de Fatima, Angelo
Sabino, Adao Aparecido
Almeida Barbosa, Luiz Claudio
Fernandes, Sergio Antonio
RSC ADVANCES, 2014, 4 (36) : 18612 - 18615
[47] BiCl3 promoted aza-Prins type cyclization:: a rapid and efficient synthesis of 2,4-disubstituted piperidines
Murty, M. S. R.
Ram, Kesur R.
Yadav, J. S.
TETRAHEDRON LETTERS, 2008, 49 (07) : 1141 - 1145
[48] Thermal Aza-Bergman Cyclization of o-Alkynylaryl Isocyanides with Organic Diselenide, Ditelluride, and Iodine Leading to 2,4-Difunctionalized Quinolines
Mitamura, Takenori
Ogawa, Akiya
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2011, 84 (07) : 791 - 793
[49] Synthesis of 2-Alkoxy(aroxy)-3-substituted Quinolines by DABCO-Promoted Cyclization of o-Alkynylaryl Isocyanides
Zhao, Jiaji
Peng, Changlan
Liu, Lanying
Wang, Yong
Zhu, Qiang
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21): : 7502 - 7504
[50] (PhTe)2-Mediated Intramolecular Radical Cyclization of o-Ethynylaryl Isocyanides Leading to Bistellurated Quinolines upon Visible-Light Irradiation
Mitamura, Takenori
Iwata, Kimiyo
Ogawa, Akiya
ORGANIC LETTERS, 2009, 11 (15) : 3422 - 3424

← 1 2 3 4 5 →