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

被引：293
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
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 23期
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
  • [21] One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using CuBr2 as catalyst
    Zhou, Haixia
    He, Miao
    Liu, Chunsheng
    Jiang, Heng
    Luo, Genxiang
    PREPARATIVE BIOCHEMISTRY & BIOTECHNOLOGY, 2006, 36 (04) : 375 - 381
  • [22] Silica-bonded N-propylsulfamic acid as a recyclable catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones
    Niknam, Khodabakhsh
    Jafarpour, Nasrolah
    Niknam, Ebrahim
    CHINESE CHEMICAL LETTERS, 2011, 22 (01) : 69 - 72
  • [23] Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using aluminum methanesulfonate as a reusable catalyst
    Song, Zhiguo
    Liu, Lianli
    Wang, Yang
    Sun, Xiaohu
    RESEARCH ON CHEMICAL INTERMEDIATES, 2012, 38 (3-5) : 1091 - 1099
  • [24] Synthesis of pyrazol-quinazolinones and 2,3-dihydroquinazolin-4(1H)-ones using CoAl2O4 nanoparticles as heterogeneous catalyst
    Ahmadian, Fatemeh
    Barmak, Alireza
    Ghaderi, Esmali
    Bavadi, Masoumeh
    Raanaei, Hossein
    Niknam, Khodabakhsh
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2019, 16 (12) : 2647 - 2658
  • [25] Trypsin-catalyzed tandem reaction: One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones by in situ formed acetaldehyde
    Xie, Zong-Bo
    Wang, Na
    Wu, Wan-Xia
    Le, Zhang-Gao
    Yu, Xiao-Qi
    JOURNAL OF BIOTECHNOLOGY, 2014, 170 : 1 - 5
  • [26] One-pot Synthesis of 3,4-Dihydropyrimidin-2 (1h) -ones Catalyzed by SO3H-Functionalized Mesopolymer under Solvent-free Conditions
    Xing, Rong
    Zhang, Tong
    Zhang, Yue
    ACTA POLYMERICA SINICA, 2014, (05): : 613 - 618
  • [27] Environmentally friendly synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones by novel Co-CNTs as recoverable catalysts
    Safari, Javad
    Gandomi-Ravandi, Soheila
    COMPTES RENDUS CHIMIE, 2013, 16 (12) : 1158 - 1164
  • [28] Lipase Catalyzed One-Pot Synthesis of 3-Methyl-4-(Hetero) Arylmethyleneisoxazole-5(4H)-Ones under Aqueous Conditions
    Kapale, Suraj S.
    Gadkari, Yatin U.
    Chaudhari, Hemchandra K.
    POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (06) : 4856 - 4865
  • [29] Green synthesis of tri/tetrasubstituted 1H-imidazoles and 2,3-dihydroquinazolin-4(1H)-ones using nano aluminium nitride as solid source of ammonia
    MARYAM HAJJAMI
    ARASH GHORBANI-CHOGHAMARANI
    ZAKIEH YOUSOFVAND
    MASOOMEH NOROUZI
    Journal of Chemical Sciences, 2015, 127 : 1221 - 1228
  • [30] Green synthesis of tri/tetrasubstituted 1H-imidazoles and 2,3-dihydroquinazolin-4(1H)-ones using nano aluminium nitride as solid source of ammonia
    Hajjami, Maryam
    Ghorbani-Choghamarani, Arash
    Yousofvand, Zakieh
    Norouzi, Masoomeh
    JOURNAL OF CHEMICAL SCIENCES, 2015, 127 (07) : 1221 - 1228
12345