A Facile Synthesis of Quinazolin-4(3H)-ones via Copper-Catalyzed One-Pot, Three-Component Tandem Reaction

被引：12
|
作者：
Dhiman, Shiv [1 ]
Nandwana, Nitesh K. [1 ]
Dhayal, Shreemala [1 ]
Saini, Hitesh K. [1 ]
Kumar, Dalip [1 ]
Kumar, Anil [1 ]
机构：
[1] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India
来源：
CHEMISTRYSELECT | 2017年 / 2卷 / 26期
关键词：
Amination; copper catalyst; C-N coupling; quinazolin-4(3H)-ones; tandem reaction; three-component reaction; C-H AMIDATION; INTRAMOLECULAR DIRECT ARYLATION; BIOLOGICAL EVALUATION; 2,3-DISUBSTITUTED QUINAZOLINONES; 2-ARYL QUINAZOLINONES; DOMINO SYNTHESIS; N-HETEROCYCLES; ARYL HALIDES; BENZIMIDAZOLES; INHIBITORS;
D O I：
10.1002/slct.201701778
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A simple and convenient one-pot, three-component tandem reaction has been developed for the synthesis of substituted quinazolin-4(3H)-ones using CuI/L-proline as catalytic system. A series of 35 quinazolin-4(3H)-ones was synthesized in good to high yield. The method involves copper-catalyzed double C-N coupling, reductive amination, condensation, cyclization and aerobic oxidation. Good functional group tolerance, mild reaction condition, readily available starting materials and user friendly procedure makes this protocol practically good and attractive method for the synthesis of quinazolin-4(3H)-ones.
引用
收藏
页码：8016 / 8019
页数：4
相关论文
共 50 条
  • [21] The Synthesis of Multisubstituted Pyrroles via a Copper-Catalyzed Tandem Three-Component Reaction
    Mou, Xue-Qing
    Xu, Zheng-Liang
    Xu, Li
    Wang, Shao-Hua
    Zhang, Bang-Hong
    Zhang, Di
    Wang, Jie
    Liu, Wei-Ting
    Bao, Wen
    ORGANIC LETTERS, 2016, 18 (16) : 4032 - 4035
  • [22] New Facile and Solvent-Free Method for the One-Pot Synthesis of Quinazolin-4(3H)-ones Catalyzed by SbCl3 under Microwave Irradiation
    Wang, Wei-Li
    Liu, Xiao-Xia
    Zhang, Tao
    Zhang, Ji-Ming
    Zhou, Jian-Hua
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2016, 38 (06): : 1196 - 1202
  • [23] Copper-catalyzed consecutive reaction to construct quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones
    Li, Ting
    Chen, Minglu
    Yang, Lei
    Xiang, Zhengxin
    Wang, Yongwei
    Li, Fei
    Chen, Dongyin
    TETRAHEDRON, 2016, 72 (06) : 868 - 874
  • [24] One-pot synthesis of 3-(2-cyanophenyl)-quinazolin-4(3H)-one
    Szczepankiewicz, W
    Suwinski, J
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2000, (07): : 922 - 924
  • [25] Copper-catalyzed tandem N-arylation/condensation: synthesis of quinazolin-4(3H)-ones from 2-halobenzonitriles and amides
    Chai, Hongxin
    Li, Jiarong
    Yang, Liupan
    Lu, Hongyan
    Qi, Zhang
    Shi, Daxin
    RSC ADVANCES, 2014, 4 (84): : 44811 - 44814
  • [26] One-pot synthesis of 3-(2-cyanophenyl)quinazolin-4(3h)-one
    Szczepankiewicz W.
    Suwinski J.
    Chemistry of Heterocyclic Compounds, 2000, 36 (07) : 809 - 810
  • [27] A General and Facile Synthesis of Novel Polysubstituted Quinazolin-4(3H)-ones
    Xin, Minhang
    Gao, Ying
    Xiang, Hua
    Chen, Dong
    He, Yi
    You, Qidong
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (01) : 169 - 174
  • [28] Synthesis of Quinazolin-4(3H)-ones via a novel approach
    Akbari, Ali
    Zahedifar, Mahboobeh
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2023, 27 (02)
  • [29] One-pot conversion of 2-nitrobenzonitriles to quinazolin-4(3H)-ones and synthesis of gefitinib and erlotinib hydrochloride
    Chandregowda, Venkateshappa
    Rao, Gudapati Venkateswara
    Reddy, Goukanapalli Chandrasekara
    HETEROCYCLES, 2007, 71 (01) : 39 - 48
  • [30] SYNTHESIS OF ISOXAZOLYL QUINAZOLIN-4 (3H)-ONES
    Rajanarendar, E.
    Venkateshwarlu, P.
    Ramakrishna, S.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 22 (02) : 95 - 98
12345