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
  • [1] Elemental Sulfur-Promoted Annulative Coupling of 2-Aminobenzamides and 2-Aminobenzylamines with Sulfoxonium Ylides: Access to Quinazolinones and Quinazolines
    Chaubey, Trayambek Nath
    Borpatra, Paran J.
    Pandey, Satyendra Kumar
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (47)
  • [2] Base dependent purported synthesis of congested 2-aminobenzylamines and tetrahydro-2-oxoquinazolines from 2-pyranones
    Farhanullah
    Samrin, Farhana
    Ram, Vishnu Ji
    TETRAHEDRON, 2009, 65 (08) : 1635 - 1638
  • [3] Synthesis of quinazolines from 2-aminobenzylamines with benzylamines and N-substituted benzylamines under transition metal-free conditions
    Tiwari, Abhishek R.
    Bhanage, Bhalchandra M.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (45) : 10567 - 10571
  • [4] A novel route for the synthesis of highly congested aryl-tethered 2-aminobenzylamines through ring transformation of 2-pyranones
    Farhanullah
    Samrin, Farhana
    Ram, Vishnu Ji
    TETRAHEDRON LETTERS, 2007, 48 (18) : 3187 - 3190
  • [5] Study of biscarbamates derived from 2-aminobenzylamines as models for alcohol prodrugs
    Papot, S
    Bachmann, C
    Combaud, D
    Gesson, JP
    TETRAHEDRON, 1999, 55 (15) : 4699 - 4708
  • [6] An Electrogenerated Base-Promoted Synthesis of 2-Aryl-3,3-Bis((Perfluoroalkyl) Thio)Acrylonitriles
    Saied, Taieb
    Raouafi, Noureddine
    Boujlel, Khaled
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2013, 188 (10) : 1320 - 1326
  • [7] Base-Promoted Synthesis of 3-Alkenyl-2-pyridones from N-Propargyl-β-enaminones and Aryl Aldehydes
    Tian, Qingyu
    Xiao, Shangyun
    Cheng, Guolin
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (10) : 2781 - 2788
  • [8] Base-promoted tandem synthesis of 2-azaaryl indoline
    Chen, Shuguang
    Tan, Jiahong
    Wu, Hao
    Zhao, Quansheng
    Shang, Yongjia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (46) : 9133 - 9137
  • [9] Base-Promoted Tandem Synthesis of 2-Azaaryl Tetrahydroquinolines
    Chen, Shuguang
    Yang, Langxuan
    Shang, Yongjia
    Mao, Jianyou
    Walsh, Patrick J.
    ORGANIC LETTERS, 2021, 23 (05) : 1594 - 1599
  • [10] Synthesis of 2-aryl quinazolines from (2-aminophenyl)methanol and oxime ether catalyzed by copper ferrite nanoparticles
    Sarode, Sachin A.
    Jadhav, Vilas G.
    Nagarkar, Jayashree M.
    TETRAHEDRON LETTERS, 2017, 58 (08) : 779 - 784
12345