One pot facile visible-light promoted synthesis of quinazolinones via Csp3-H oxidation in aqueous media

被引:3
|
作者
Chen, Taiping [1 ,2 ]
Yang, Huan [3 ]
Li, Shuangjun [1 ]
Xie, Jiangping [1 ]
Wei, Lingyu [1 ]
Yang, Li [1 ]
机构
[1] Yibin Univ, Sichuan Univ, Key Lab Proc Anal & Control, Yibin 644000, Sichuan, Peoples R China
[2] Xihua Univ, Party Working Comm, Yibin Campus, Yibin 644000, Sichuan, Peoples R China
[3] Xihua Univ, Coll Sci, Chengdu 610039, Sichuan, Peoples R China
关键词
Visible-light promoted; Csp3-H oxidation; Quinazolinones; Aqueous; TANDEM SYNTHESIS; ALCOHOLS; 2-AMINOBENZAMIDES; FUNCTIONALIZATION;
D O I
10.1016/j.tetlet.2023.154788
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The utilization of biocompatible catalysts for the synthesis of biologically significant molecules in aqueous environments represents a pivotal and challenging aspect within the realm of green and sustainable chemistry. Herein, a KI-mediated Csp3-H oxidation reaction to synthesis heterogeneously of quinazolinones is reported in this study. Aldehydes, formed from the oxidation of alcohols, undergo amide attacks and subsequent cyclization, efficiently producing a variety of quinazolinones under sunlight and in aqueous media. The utilization of solar energy significantly reduces experimental costs and minimizes the occurrence of toxic effects. This approach proceeded smoothly to afford quniazolinones in high to excellent yields with a wide substrate scope.
引用
收藏
页数:4
相关论文
共 50 条
  • [21] Naphthoquinone-Directed C-H Annulation and Csp3-H Bond Cleavage: One-Pot Synthesis of Tetracyclic Naphthoxazoles
    Wang, Meining
    Zhang, Chi
    Sun, Li-Ping
    Ding, Chunyong
    Zhang, Ao
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10): : 4553 - 4560
  • [22] A FACILE AND CONVENIENT METHOD TO THE ONE-POT SYNTHESIS OF 2-MERCAPTO-4(3H)-QUINAZOLINONES
    Nikpour, Farzad
    Mozafari, Roya
    Paibast, Touraj
    HETEROCYCLES, 2009, 78 (06) : 1569 - 1571
  • [23] Combination of Copper Catalysis and Visible Light Photocatalysis: Selective Csp3-H Functionalization of Ethers with Diazomalonates
    Wang, Jin-Ge
    You, Fang-Bo
    Osman, S.
    Chen, Jun-Yi
    Xia, Xu-Dong
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (09) : 1555 - 1562
  • [24] Visible-Light-Induced Photocatalytic Aerobic Oxidative Csp3-H Functionalization of Glycine Derivatives: Synthesis of Substituted Quinolines
    Yang, Xiaorong
    Li, Liqi
    Li, Ying
    Zhang, Yuan
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (24): : 12433 - 12442
  • [25] Expeditious Diastereoselective Synthesis of Elaborated Ketones via Remote Csp3-H Functionalization
    Nevado, Cristina
    Shu, Wei
    SYNLETT, 2017, 28 (06) : A67 - A70
  • [26] An Efficient Synthesis of Polysubstituted Pyridines via Csp3-H Oxidation and C-S Cleavage of Dimethyl Sulfoxide
    Wu, Xia
    Zhang, Jingjing
    Liu, Shan
    Gao, Qinghe
    Wu, Anxin
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (02) : 218 - 225
  • [27] Expeditious Diastereoselective Synthesis of Elaborated Ketones via Remote Csp3-H Functionalization
    Shu, W.
    Lorente, A.
    Gomez-Bengoa, E.
    Nevado, C.
    SYNTHESIS-STUTTGART, 2017, 49 (07): : A57 - A71
  • [28] Expeditious diastereoselective synthesis of elaborated ketones via remote Csp3-H functionalization
    Shu, Wei
    Lorente, Adriana
    Gomez-Bengoa, Enrique
    Nevado, Cristina
    NATURE COMMUNICATIONS, 2017, 8
  • [29] One-pot facile synthesis of PEGylated Au nanoparticles in an aqueous media
    Camli, Sevket Tolga
    Buyukserin, Fatih
    Yavuz, Cafer T.
    Yavuz, Mustafa Selman
    MATERIALS CHEMISTRY AND PHYSICS, 2012, 134 (2-3) : 1153 - 1159
  • [30] Iodine-promoted sequential dual oxidative Csp3-H amination/Csp3-H iodination reactions: efficient synthesis of 1-iodoimidazo[1,5-a] pyridines
    Wu, Yan-Dong
    Geng, Xiao
    Gao, Qinghe
    Zhang, Jingjing
    Wu, Xia
    Wu, An-Xin
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (11): : 1430 - 1434