New Strategy for the Synthesis of Heterocycles via Copper-Catalyzed Oxidative Decarboxylative Amination of Glyoxylic Acid

被引：5

作者：

Niu, Bin ^{[1
]}

Li, Shaoqing ^{[1
]}

Cui, Chang ^{[1
]}

Yan, Yizhe ^{[1
]}

Tang, Lin ^{[3
]}

Wang, Jianyong ^{[2
]}

机构：

[1] Zhengzhou Univ Light Ind, Henan Key Lab Cold Chain Food Qual & Safety Contr, Henan Collaborat Innovat Ctr Food Prod & Safety, Sch Food & Biol Engn, Zhengzhou 450000, Henan, Peoples R China

[2] Qilu Univ Technol, Shandong Acad Sci, Sch Light Ind & Engn, Jinan 250353, Shandong, Peoples R China

[3] Xinyang Normal Univ, Coll Chem & Chem Engn, Xinyang 464000, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 48期

基金：

中国国家自然科学基金;

关键词：

Glyoxylic acid; Copper; Decarboxylation; C-N coupling; Heterocycles; BOND FORMATION; ARYL HALIDES; FUNCTIONALIZATION; QUINAZOLINONES; FORMYLATION; 1,3,5-TRIAZINES; HYDROFORMYLATION; ACTIVATION; INHIBITORS; QUINOLINE;

D O I：

10.1002/ejoc.201901538

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed oxidative decarboxylative amination of glyoxylic acid with substrates having two nitrogen-nucleophilic sites was first demonstrated. Using this novel approach, 1,3,5-triazines, quinazolinones and quinazolines were obtained in up to 93 % yields. Notably, glyoxylic acid was employed as the C1 synthon for heterocycles. This strategy enriches the application of glyoxylic acid for the synthesis of valuable heterocycles.

引用

页码：7800 / 7803

页数：4

共 50 条

[21] Copper-catalyzed oxidative multicomponent reaction: synthesis of imidazo fused heterocycles with molecular oxygen
Li, Xianwei
Wang, Tianzhang
Lu, Yu-Jing
Ji, Shaomin
Huo, Yanping
Liu, Bifu
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (39) : 7143 - 7151
[22] Copper-catalyzed decarboxylative coupling reactions for the synthesis of proparal amines
Lim, Jeongah
Park, Kyungho
Byeun, Aleum
Lee, Sunwoo
TETRAHEDRON LETTERS, 2014, 55 (35) : 4875 - 4878
[23] Copper-catalyzed Decarboxylative Hydroboration: Synthesis of Vinyl Boronic Esters
Irudayanathan, Francis Mariaraj
Raja, Gabriel Charles Edwin
Kim, Han-Sung
Na, Kyungsu
Lee, Sunwoo
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2016, 37 (04) : 463 - 468
[24] Copper-Catalyzed Electrophilic Amination: An Umpolung Strategy for New C -N Bond Formations
Hirano, Koji
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2023, 96 (03) : 198 - 207
[25] Copper-Catalyzed Aerobic Oxidative Amination of Indole Derivatives via Single-Electron Transfer
Zhao, Peizheng
Wang, Ke
Yue, Yuanyuan
Chao, Junli
Ye, Yaqing
Tang, Qinghu
Liu, Jianming
CHEMCATCHEM, 2020, 12 (12) : 3207 - 3211
[26] COPPER-CATALYZED REACTIONS FOR THE SYNTHESIS OF BIOLOGICALLY ACTIVE HETEROCYCLES
Beifuss, Uwe
MEDICINAL CHEMISTRY RESEARCH, 2010, 19 : S9 - S10
[27] Copper-catalyzed synthesis of quinoline derivatives via tandem Knoevenagel condensation, amination and cyclization
Dhiman, Shiv
Saini, Hitesh Kumar
Nandwana, Nitesh Kumar
Kumar, Dalip
Kumar, Anil
RSC ADVANCES, 2016, 6 (29): : 23987 - 23994
[28] Synthesis of Polyfunctional Pyridines via Copper-Catalyzed Oxidative Coupling Reactions
Fu, Yajie
Wang, Panpan
Guo, Xin
Wu, Ping
Meng, Xu
Chen, Baohua
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23): : 11671 - 11677
[29] Synthesis of Terminal Allenes via a Copper-Catalyzed Decarboxylative Coupling Reaction of Alkynyl Carboxylic Acids
Lim, Jeongah
Choi, Jinseop
Kim, Han-Sung
Kim, In Seon
Nam, Kye Chun
Kim, Jimin
Lee, Sunwoo
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (01): : 303 - 308
[30] Practical synthesis of pyrazoles via a copper-catalyzed relay oxidation strategy
Tang, Xiaodong
Huang, Liangbin
Yang, Jidan
Xu, Yanli
Wu, Wanqing
Jiang, Huanfeng
CHEMICAL COMMUNICATIONS, 2014, 50 (94) : 14793 - 14796

← 1 2 3 4 5 →