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
  • [31] Gallium(III) triflate-catalyzed one-pot selective synthesis of 2 3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones
    Chen, Jiuxi
    Wu, Dengze
    He, Fei
    Liu, Miaochang
    Wu, Huayue
    Ding, Jinchang
    Su, Weike
    TETRAHEDRON LETTERS, 2008, 49 (23) : 3814 - 3818
  • [32] Ecofriendly synthesis of quinazolin-4(3H)-ones
    Kidwai, M
    Rastogi, R
    Rastogi, S
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2004, 43 (02): : 423 - 425
  • [33] Synthesis of quinazolin-4(3H)-ones, an update
    Picos-Corrales, Lorenzo A.
    Sarmiento-Sanchez, Juan I.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2018, 54 (08) : 762 - 764
  • [34] Practical highly enantioselective synthesis of propargylamines through a copper-catalyzed one-pot three-component condensation reaction
    Gommermann, Nina
    Knochel, Paul
    CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (16) : 4380 - 4392
  • [35] Reaction of Imidoformates with Anthranilates: Facile, One-Pot, Three-Component Synthesis of 8H-Quinazolino[4,3-b]quinazolin-8-ones
    Venkateswarlu, S.
    Satyanarayana, M.
    Ravikiran, P.
    Siddaiah, V.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (05) : 1089 - 1093
  • [36] Synthesis of Quinazolin-4(3H)-ones via the Reaction of 2-Halobenzamides with Nitriles
    Yu, Xiaoqiang
    Gao, Linqi
    Jia, Linan
    Yamamoto, Yoshinori
    Bao, Ming
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (17): : 10352 - 10358
  • [37] INCREDIBLY PRODUCTIVE ONE-POT SYNTHESIS OF QUINAZOLIN-4(3H)- ONES USING TRIS(PENTAFLUOROPHENYL)BORANE AS AN EFFECTIVE CATALYST
    Venkateswarlu, A.
    Reddy, P. Suresh
    Kumar, G. Vijay
    Krishna, M. Hari
    Thriveni, P.
    HETEROCYCLIC LETTERS, 2024, 14 (03): : 675 - 681
  • [38] Copper(I) Iodide Catalyzed Domino Process to Quinazolin-4(3H)-ones
    Zhou, Jing
    Fu, Liangbing
    Lv, Man
    Liu, Jinsong
    Pei, Duanqing
    Ding, Ke
    SYNTHESIS-STUTTGART, 2008, (24): : 3974 - 3980
  • [39] One-Pot Three Component Synthesis of Quinazolin-4(3H)-One Derivatives: Investigation of Photophysical Properties and FRET Application toward Protein Lysozyme
    Sarkar, Soumen
    Mandal, Subhro
    Pramanik, Animesh
    POLYCYCLIC AROMATIC COMPOUNDS, 2024, 44 (03) : 1896 - 1917
  • [40] Palladium-catalyzed three-component carbonylative synthesis of 2-(trifluoromethyl)quinazolin-4(3H)-ones from trifluoroacetimidoyl chlorides and amines
    Chen, Zhengkai
    Wang, Le-Cheng
    Zhang, Jiajun
    Wu, Xiao-Feng
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (17): : 2499 - 2504