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
  • [1] Visible Light Promoted Benzylic CSp3-H Bond Activation and Functionalization
    Pei Pengkun
    Zhang Fan
    Yi Hong
    Lei Aiwen
    ACTA CHIMICA SINICA, 2017, 75 (01) : 15 - 21
  • [2] Visible-light induced oxidative Csp3-H activation of methyl aromatics to methyl esters
    Zhang, Lingling
    Yi, Hong
    Wang, Jue
    Lei, Aiwen
    GREEN CHEMISTRY, 2016, 18 (19) : 5122 - 5126
  • [3] Benzylic Hydroperoxidation via Visible-Light-Induced Csp3-H Activation
    Inoa, Joan
    Patel, Mansi
    Dominici, Grecia
    Eldabagh, Reem
    Patel, Anjali
    Lee, John
    Xing, Yalan
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (09): : 6181 - 6187
  • [4] Visible-light promoted one-pot synthesis of pyrazoles from alkynes and hydrazines
    Meng, Yunge
    Zhang, Te
    Gong, Xinchi
    Zhang, Min
    Zhu, Chunyin
    TETRAHEDRON LETTERS, 2019, 60 (02) : 171 - 174
  • [5] Visible light-promoted Selectfluor- mediated quinone functionalization with unactivated Csp3-H components
    Kulthe, Arun D.
    Nadiveedhi, Maheshwara Reddy
    Mainkar, Prathama S.
    Akondi, Srirama Murthy
    ARKIVOC, 2021, : 115 - 124
  • [6] Synthesis of Cu-catalysed quinazolinones using a Csp3-H functionalisation/cyclisation strategy
    Gholap, Aniket V. A.
    Maity, Soham
    Schulzke, Carola
    Maiti, Debabrata
    Kapdi, Anant R.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (34) : 7140 - 7146
  • [7] Visible light bromide catalysis for oxazoline, pyrrolidine, and dihydrooxazine syntheses via Csp3-H functionalizations
    Kaur, Navdeep
    Ziegelmeyer, Elizabeth C.
    Farinde, Olutayo N.
    Truong, Jonathon T.
    Huynh, Michelle M.
    Li, Wei
    CHEMICAL COMMUNICATIONS, 2021, 57 (80) : 10387 - 10390
  • [8] One-pot synthesis of quinazolinones and quinazolines under visible light via decarboxylation of α-hydroxy acids
    Xie, Zongbo
    Yang, Jiangnan
    Hu, Jiayu
    Fan, Qiangwen
    Zhu, Haibo
    Le, Zhanggao
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2023, 60 (04) : 681 - 691
  • [9] Iron-catalyzed one-pot sequential transformations: Synthesis of quinazolinones via oxidative Csp3-H bond activation using a new metal-organic framework as catalyst
    To, Tuong A.
    Vo, Yen H.
    Nguyen, Hue T. T.
    Ha, Phuong T. M.
    Doan, Son H.
    Doan, Tan L. H.
    Li, Shuang
    Le, Ha V.
    Tu, Thach N.
    Phan, Nam T. S.
    JOURNAL OF CATALYSIS, 2019, 370 : 11 - 20
  • [10] One pot synthesis of 4(3H)-quinazolinones
    Bhat, BA
    Sahu, DP
    SYNTHETIC COMMUNICATIONS, 2004, 34 (12) : 2169 - 2176