A convenient palladium-catalyzed carbonylative synthesis of quinazolines from 2-aminobenzylamine and aryl bromides

被引：31
|
作者：
Chen, Jianbin [1 ]
Natte, Kishore [1 ]
Neumann, Helfried [1 ]
Wu, Xiao-Feng [1 ]
机构：
[1] Univ Rostock, Leibniz Inst Katalyse, D-18059 Rostock, Germany
来源：
RSC ADVANCES | 2014年 / 4卷 / 99期
关键词：
STOICHIOMETRIC CARBON-MONOXIDE; ONE-POT SYNTHESIS; O-PHENYL OXIMES; AEROBIC OXIDATION; CASCADE SYNTHESIS; DOMINO REACTIONS; DERIVATIVES; HETEROCYCLES; NUCLEOPHILES; INHIBITORS;
D O I：
10.1039/c4ra11303a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel and practical strategy towards quinazoline scaffolds synthesis has been achieved. Through palladium-catalyzed carbonylative coupling of 2-aminobenzylamine with aryl bromides, the desired quinazolines were produced in moderate to good yields for the first time. The reactions followed an aminocarbonylation-condensation-oxidation sequence in a one-pot one-step manner. Preliminary investigation showed DMSO serves both as solvent and oxidant in this procedure.
引用
收藏
页码：56502 / 56505
页数：4
相关论文
共 50 条
  • [21] Palladium-catalyzed carbonylative synthesis of quinazolines: Silane act as better nucleophile than amidine
    Lu, Jia-Ming
    Huo, Yong-Wang
    Qi, Xinxin
    Wu, Xiao-Feng
    MOLECULAR CATALYSIS, 2021, 509
  • [22] Palladium-Catalyzed Benzylic C(sp3)-H Carbonylative Arylation with Aryl Bromides
    Hu, Bowen
    Zhao, Haoqiang
    Wu, Yu
    Walsh, Patrick J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (23)
  • [23] Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides Using Near Stoichiometric Carbon Monoxide
    Neumann, Karoline T.
    Laursen, Simon R.
    Lindhardt, Anders T.
    Bang-Andersen, Benny
    Skrydstrup, Troels
    ORGANIC LETTERS, 2014, 16 (08) : 2216 - 2219
  • [24] A Convenient and Practical Synthesis of Anisoles and Deuterated Anisoles by Palladium-Catalyzed Coupling Reactions of Aryl Bromides and Chlorides
    Gowrisankar, Saravanan
    Neumann, Helfried
    Beller, Matthias
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (09) : 2498 - 2502
  • [25] Palladium-catalyzed carbonylative transformation of aryl chlorides and aryl tosylates
    Wu, Xiao-Feng
    RSC ADVANCES, 2016, 6 (87): : 83831 - 83837
  • [26] Palladium-catalyzed carbonylative synthesis of α,β-unsaturated amides from aryl azides and alkenylaluminum reagent
    Chen, Bo
    Wu, Xiao-Feng
    JOURNAL OF CATALYSIS, 2020, 383 (383) : 160 - 163
  • [27] Palladium-Catalyzed Carbonylative Synthesis of Heterocycles
    Feng, Jian-Bo
    Wu, Xiao-Feng
    HETEROCYCLIC CHEMISTRY IN THE 21ST CENTURY: A TRIBUTE TO ALAN KATRITZKY, 2017, 121 : 207 - 246
  • [28] Palladium-Catalyzed Carbonylative Synthesis of Benzogerminones
    Chen, Bo
    Wu, Xiao-Feng
    SYNLETT, 2019, 30 (13) : 1592 - 1596
  • [29] Palladium-catalyzed α-arylation of aldehydes with aryl bromides
    Terao, Y
    Fukuoka, Y
    Satoh, T
    Miura, M
    Nomura, M
    TETRAHEDRON LETTERS, 2002, 43 (01) : 101 - 104
  • [30] PALLADIUM-CATALYZED CARBONYLATIVE COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES
    ECHAVARREN, AM
    STILLE, JK
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) : 1557 - 1565
12345