Base-Promoted Synthesis of 2-Aryl Quinazolines from 2-Aminobenzylamines in Water

被引：56
|
作者：
Chatterjee, Tanmay [1 ]
Kim, Dong In [2 ]
Cho, Eun Jin [2 ]
机构：
[1] Birla Inst Technol & Sci, Dept Chem, Hyderabad Campus, Pilani 500078, Telangana, India
[2] Chung Ang Univ, Dept Chem, 84 Heukseok Ro, Seoul 06974, South Korea
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 14期
基金：
新加坡国家研究基金会;
关键词：
AEROBIC OXIDATIVE SYNTHESIS; COPPER-CATALYZED SYNTHESIS; VISIBLE-LIGHT PHOTOREDOX; 2-SUBSTITUTED QUINAZOLINES; CASCADE SYNTHESIS; DOMINO REACTION; ARYL; MULTICOMPONENT; BENZYLAMINES; HETEROCYCLES;
D O I：
10.1021/acs.joc.8b00327
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A transition-metal-free procedure for the synthesis of a highly valuable class of heteroaromatics, quinazolines, was developed by using easily available 2-aminobenzylamines and alpha,alpha,alpha-trihalotoluenes. The transformation proceeded smoothly in the presence of only sodium hydroxide and molecular oxygen in water at 100 degrees C, furnishing a variety of 2-aryl quinazolines. The crystallization process of the crude reaction mixture for the purification of the solid products circumvents huge solvent consuming workup and column chromatographic techniques, which make the overall process more sustainable and economical.
引用
收藏
页码：7423 / 7430
页数：8
相关论文
共 50 条
  • [31] A Base- and Metal-free Protocol for the Synthesis of 2-Aryl/heteroaryl Thiazolines
    Chaudhary, Shweta
    Milton, Marilyn D.
    Garg, Parul
    CHEMISTRYSELECT, 2017, 2 (02): : 650 - 654
  • [32] BASE-PROMOTED REARRANGEMENT OF 2,3-EPOXYCYCLOHEXANONES TO PHENOIS
    BELLESIA, F
    GHELFI, F
    GRANDI, R
    PAGNONI, UM
    JOURNAL OF CHEMICAL RESEARCH-S, 1985, (12): : 400 - 401
  • [33] Synthesis and antimicrobial activities of His(2-aryl)Arg and Trp-His(2-aryl) classes of dipeptidomimetics
    Mahindra, Amit
    Sharma, Krishna K.
    Rathore, Dinesh
    Khan, Shabana. I.
    Jacob, Melissa R.
    Jain, Rahul
    MEDCHEMCOMM, 2014, 5 (05) : 671 - 676
  • [34] Base-promoted synthesis of diarylsulfones from sulfonyl hydrazines and diaryliodonium salts
    Gong, Bozhen
    Zhu, Haibo
    Yang, Liu
    Wang, Haifeng
    Fan, Qiangwen
    Xie, Zongbo
    Le, Zhanggao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (17) : 3501 - 3505
  • [35] Base-catalyzed synthesis of N-(2-arylethyl)anilines and base-promoted domino synthesis of 2,3-dihydroindoles
    Beller, M
    Breindl, C
    Riermeier, TH
    Eichberger, M
    Trauthwein, H
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (24) : 3389 - 3391
  • [36] Base-Promoted Multicomponent Reactions: A Synthesis of 2-Amino-1,3-selenazole Derivatives
    Liu, Hua-Wei
    Fang, Yi
    Wang, Shun-Yi
    Ji, Shun-Jun
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05): : 3508 - 3516
  • [37] Electrochemically generated base-promoted synthesis and biological activities of 2,4-disubstituted carbonotrithioates
    Medini, Hayet
    Medini, Faten
    Mekni, Nejib Hussein
    Ksouri, Riadh
    Legault, Jean
    Boujlel, Khaled
    JOURNAL OF SULFUR CHEMISTRY, 2015, 36 (03) : 308 - 316
  • [38] SYNTHESIS OF 1-ARYL-3-METHYLTRIAZENES BY BASE-PROMOTED DECOMPOSITION OF 1-ARYL-3-HYDROXYMETHYL-3-METHYLTRIAZENES
    CHENG, SC
    ILEY, J
    JOURNAL OF CHEMICAL RESEARCH-S, 1983, (12): : 320 - 321
  • [39] Base-Promoted Selective Synthesis of 2H-Pyranones and Tetrahydronaphthalenes via Domino Reactions
    Thimmarayaperumal, Solaimalai
    Shanmugam, Sivakumar
    ACS OMEGA, 2017, 2 (08): : 4900 - 4910
  • [40] Base-Promoted Synthesis of Isoquinolines through a Tandem Reaction of 2-Methyl-arylaldehydes and Nitriles
    Shuai, Sujuan
    Mao, Jianyou
    Zhou, Fan
    Yan, Qifeng
    Chen, Lingfeng
    Li, Jie
    Walsh, Patrick J.
    Liang, Guang
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (10): : 6793 - 6797
12345