Electrochemical Synthesis of Quinazolines: N-H/C(sp3)-H Coupling of o-Carbonyl Anilines with Amino Acids and Amines

被引：0

作者：

Wu, Jiwei ^{[1
]}

Yu, Lingxiang ^{[1
]}

Li, Kaixuan ^{[1
]}

Zhang, Di ^{[1
]}

Ye, Longqiang ^{[1
]}

Xu, Xiaolan ^{[2
]}

Zhou, Jie ^{[3
]}

Li, Zirong ^{[1
]}

Xu, Huajian ^{[3
]}

机构：

[1] Anhui Sci & Technol Univ, Coll Chem & Mat Engn, Fengyang 233100, Peoples R China

[2] Anhui Med Univ, Sch Med Sci, Hefei 230009, Peoples R China

[3] Hefei Univ Technol, Sch Food & Biol Engn, Hefei 230009, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 23期

基金：

中国国家自然科学基金;

关键词：

H BOND; DERIVATIVES; AMINATION; 2-ARYLQUINAZOLINES; CANCER; ANNULATION;

D O I：

10.1021/acs.joc.4c01173

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient electrochemical protocol for the synthesis of quinazolines through N-H/C(sp3)-H coupling of o-carbonyl anilines with natural amino acids/amines has been developed. The products quinazolines can easily be isolated in moderate to excellent yields under external chemical oxidant-free conditions. Moreover, this reaction can be safely conducted on gram scale.

引用

页码：17031 / 17041

页数：11

共 50 条

[1] Electrochemical Oxidative Coupling Between Benzylic C(sp3)-H and N-H of Secondary Amines: Rapid Synthesis of α-Amino α-Aryl Esters
Nagare, Yadav Kacharu
Shah, Imtiyaz Ahmad
Yadav, Jyothi
Pawar, Amol Prakash
Choudhary, Rahul
Chauhan, Pankaj
Kumar, Indresh
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (14): : 9682 - 9691
[2] Electrochemical α-C(sp3)-H/N-H Cross-Coupling of Isochromans and Azoles
Li, Guoping
Yan, Bing
Wu, Liangliang
Li, Yabo
Hao, Xinqi
Gong, Ming
Wu, Yangjie
MOLECULES, 2025, 30 (01):
[3] Electrochemical Oxidative C(sp3)-H/N-H Coupling of Diarylmethanes with Sulfoximines or Benzophenone Imine
Kong, Xianqiang
Tian, Yan
Chen, Xiaohui
Chen, Yiyi
Wang, Wei
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (19): : 13610 - 13617
[4] Electrocatalytic Intermolecular C(sp3)-H/N-H Coupling of Methyl N-Heteroaromatics with Amines and Amino Acids: Access to Imidazo-Fused N-Heterocycles
Qian, Peng
Yan, Zicong
Zhou, Zhenghong
Hu, Kangfei
Wang, Jiawei
Li, Zhibin
Zha, Zhenggen
Wang, Zhiyong
ORGANIC LETTERS, 2018, 20 (20) : 6359 - 6363
[5] Coupling N-H Deprotonation, C-H Activation, and Oxidation: Metal-Free C(sp3)-H Aminations with Unprotected Anilines
Evoniuk, Christopher J.
Gomes, Gabriel dos Passos
Hill, Sean P.
Fujita, Satoshi
Hanson, Kenneth
Alabugin, Igor V.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (45) : 16210 - 16221
[6] Electrochemical Oxidative C-H/N-H Coupling between γ-Lactams and Anilines
Gong, Ming
Huang, Jing-Mei
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (40) : 14293 - 14296
[7] Electrochemical Intramolecular Oxidative C(sp3)-H/C(sp3)-H Coupling for the Synthesis of 4-Quinolones
Wu, Jiwei
Jin, Kejun
Wang, Ruiyou
Wang, Xingyu
Yu, Xiaoxiao
Zhong, Liangcheng
Liu, Jianguo
SYNTHESIS-STUTTGART, 2023, 55 (03): : 451 - 456
[8] Electrochemical Oxidative C(sp3)-H/N-H Cross-Coupling for N-Mannich Bases with Hydrogen Evolution
Wang, Pan
Yang, Zhenlin
Wu, Ting
Xu, Chenyang
Wang, Ziwei
Lei, Aiwen
CHEMSUSCHEM, 2019, 12 (13) : 3073 - 3077
[9] Electrochemical oxidative C(sp3)-H/O-H cross-coupling for the synthesis of α-acyloxyketones
Wu, Jiwei
Shi, Haowen
Liu, Jianguo
Wang, Ruiyou
Zhou, Jie
Xu, Xiao-Lan
Xu, Hua-Jian
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (10): : 2459 - 2464
[10] Coordinating activation strategy for C(sp3)-H/C(sp3)-H cross-coupling to access β-aromatic α-amino acids
Li, Kaizhi
Wu, Qian
Lan, Jingbo
You, Jingsong
NATURE COMMUNICATIONS, 2015, 6

← 1 2 3 4 5 →