Gallium(III) triflate-catalyzed one-pot selective synthesis of 2 3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones

被引:288
|
作者
Chen, Jiuxi [1 ]
Wu, Dengze [1 ]
He, Fei [1 ]
Liu, Miaochang [1 ]
Wu, Huayue [1 ]
Ding, Jinchang [1 ]
Su, Weike [1 ,2 ]
机构
[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325027, Peoples R China
[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Zhejiang Key Lab Pharmaceut Engn, Hangzhou 310014, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
gallium(III) triflate; 2,3-dihydroquinazolin-4(1H)-ones; quinazolin-4(3H)-ones; one-pot; selective synthesis;
D O I
10.1016/j.tetlet.2008.03.127
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H) -ones have been synthesized in good to excellent yields and high selectivity by one-pot reaction using isatoic anhydride, ammonium acetate (or amines), and aldehydes in ethanol or in DMSO under mild conditions, respectively. The reaction was efficiently prompted by 1 mol % Ga(OTf)(3) and the catalyst could be recovered easily after the reactions and reused without evident loss of reactivity. (C) 2008 Published by Elsevier Ltd.
引用
收藏
页码:3814 / 3818
页数:5
相关论文
共 50 条
  • [1] Iodine: Selectively Promote the Synthesis of Mono Substituted Quinazolin-4(3H)-ones and 2,3-Dihydroquinazolin-4(1H)-ones in One-Pot
    Zeng, Li-Yan
    Cai, Chun
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (05) : 1035 - 1039
  • [2] Selective synthesis of 2-substituted 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones catalyzed by Schiff base dioxomolybdenum(VI) complex
    Feng, Mengmeng
    Yan, Qingmin
    Yang, Lan
    Ye, Yanan
    Liu, Gang
    Wang, Weili
    [J]. INTERNATIONAL JOURNAL OF CHEMICAL KINETICS, 2023, 55 (03) : 119 - 128
  • [3] Efficient one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones from aromatic aldehydes and their one-pot oxidation to quinazolin-4(3H)-ones catalyzed by Bi(NO3)3•5H2O: Investigating the role of the catalyst
    Mohammadpoor-Baltork, Iraj
    Khosropour, Ahmad R.
    Moghadam, Majid
    Tangestaninejad, Shahram
    Mirkhani, Valiollah
    Baghersad, Saeid
    Mirjafari, Arsalan
    [J]. COMPTES RENDUS CHIMIE, 2011, 14 (10) : 944 - 952
  • [4] One-pot synthesis of quinazolin-4(3 H)-ones and 2,3-dihydroquinazolin-4(1 H)-ones utilizing N-(2-aminobenzoyl)benzotriazoles
    Senol, Ilbilge Merve
    Celik, Ilhami
    Avan, Ilker
    [J]. TURKISH JOURNAL OF CHEMISTRY, 2019, 43 (06) : 1580 - +
  • [5] 2,3-Dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones as broad-spectrum cytotoxic agents and their impact on tubulin polymerisation
    O'Brien, Nicholas S.
    Gilbert, Jayne
    McCluskey, Adam
    Sakoff, Jennette A.
    [J]. RSC MEDICINAL CHEMISTRY, 2024, 15 (05): : 1686 - 1708
  • [6] Strontium chloride-catalyzed one-pot synthesis of 2, 3-dihydroquinazolin-4(1H)-ones in protic media
    Wang, Min
    Zhang, Ting Ting
    Liang, Yan
    Gao, Jing Jing
    [J]. CHINESE CHEMICAL LETTERS, 2011, 22 (12) : 1423 - 1426
  • [7] Zirconyl(IV) Chloride Catalyzed Three Component One-pot Synthesis of Quinazolin-4(3H)-ones
    Jaiprakash N. Sangshetti
    Nagnnath D. Kokare
    Devanand B. Shinde
    [J]. Monatshefte für Chemie - Chemical Monthly, 2007, 138 : 1289 - 1291
  • [8] One-pot synthesis of substituted quinazolin-4(3H)-ones under microwave irradiation
    Rad-Moghadam, K
    Khajavi, MS
    [J]. JOURNAL OF CHEMICAL RESEARCH-S, 1998, (11): : 702 - 703
  • [9] Zirconyl(IV) chloride catalyzed three component one-pot synthesis of quinazolin-4(3H)-ones
    Sangshetti, Jaiprakash N.
    Kokare, Nagnnath D.
    Shinde, Devanand B.
    [J]. MONATSHEFTE FUR CHEMIE, 2007, 138 (12): : 1289 - 1291
  • [10] Base promoted metal-free approach towards synthesis of quinazolin-4 (3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones under microwave irradiation
    Dutta, Apurba
    Sarma, Diganta
    [J]. SUSTAINABLE CHEMISTRY AND PHARMACY, 2021, 20