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
收藏
页码:17031 / 17041
页数:11
相关论文
共 50 条
  • [21] Copper-catalyzed C(sp3)-H/N-H Cross Dehydrogenative Coupling Between Toluene Derivatives and Picolinamides
    Ji, Huihui
    Zhan, Hongju
    Chen, Shumin
    Fang, Zeguo
    Zhang, Qian
    Li, Dong
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (10)
  • [22] C(sp3)-H/C(sp3)-H Dehydrogenative Radical Coupling of Glycine Derivatives
    Wang, Jiayuan
    Ye, Youwan
    Sang, Tongzhi
    Zhou, Chenxing
    Bao, Xiazhen
    Yuan, Yong
    Huo, Congde
    ORGANIC LETTERS, 2022, 24 (41) : 7577 - 7582
  • [23] Intermolecular Amination of UnactivatedC(sp3)-H Bonds with Cyclic Alkylamines: Formation of C(sp3)-N Bonds through Copper/Oxygen-Mediated C(sp3)-H/N-H Activation
    Gou, Quan
    Yang, Yu-Wen
    Liu, Zi-Ning
    Qin, Jun
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (45) : 16057 - 16061
  • [24] A copper/O2-mediated direct sp3 C-H/N-H cross-dehydrogen coupling reaction of acylated amines and N-aryl glycine esters
    Sun, Bin
    Wang, Yao
    Li, Deyu
    Jin, Can
    Su, Weike
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (16) : 2902 - 2909
  • [25] Synthesis of Tricyclic Nitrogen Heterocycles by a Sequence of Palladium-Catalyzed N-H and C(sp3)-H Arylations
    Guyonnet, Mathieu
    Baudoin, Olivier
    ORGANIC LETTERS, 2012, 14 (01) : 398 - 401
  • [26] Cobalt-Catalyzed Oxidative C(sp3)-H Phosphonylation for α-Aminophosphonates via C(sp3)-H/P(O)-H Coupling
    Lin, Binzhou
    Shi, Shanshan
    Lin, Rongcan
    Cui, Yiqun
    Fang, Meijuan
    Tang, Guo
    Zhao, Yufen
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (12): : 6754 - 6761
  • [27] Electrochemical C(sp3)-H Fluorination
    Takahira, Yusuke
    Chen, Miao
    Kawamata, Yu
    Mykhailiuk, Pavel
    Nakamura, Hugh
    Peters, Byron K.
    Reisberg, Solomon H.
    Li, Chao
    Chen, Longrui
    Hoshikawa, Tamaki
    Shibuguchi, Tomoyuki
    Baran, Phil S.
    SYNLETT, 2019, 30 (10) : 1178 - 1182
  • [28] Ammonium Persulfate Mediated Oxidative C(sp3)-H/N-H Cross-Coupling for Synthesis of Hemiaminal Ethers Under Mild Conditions
    Wu, Jiwei
    Zhu, Jianye
    Yu, Lingxiang
    Yu, Xiaoxiao
    Li, Wen
    Xie, Lianyu
    Wu, Ji
    Li, Zirong
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (12)
  • [29] Selective Iodine-Catalyzed Intermolecular Oxidative Amination of C(sp3)-H Bonds with ortho-Carbonyl-Substituted Anilines to Give Quinazolines
    Yan, Yizhe
    Zhang, Yonghui
    Feng, Chengtao
    Zha, Zhenggen
    Wang, Zhiyong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (32) : 8077 - 8081
  • [30] Recent advances in γ-C(sp3)-H bond activation of amides, aliphatic amines, sulfanilamides and amino acids
    Ni, Shao-Fei
    Huang, Guanglong
    Chen, Yonghui
    Wright, James S.
    Li, Mingde
    Dang, Li
    COORDINATION CHEMISTRY REVIEWS, 2022, 455