Silver(II) oxide-mediated synthesis of 2,4-diarylquinazolines

被引:1
作者
Cheung, Wing [1 ]
Patch, Raymond J. [1 ]
Player, Mark R. [1 ]
机构
[1] Janssen Res & Dev, Cardiovasc & Metab TA, Welch & McKean Rd, Spring House, PA 19477 USA
关键词
Diarylquinazoline; N-arylbenzamidine; Silver oxide; Radical oxidation; ONE-POT SYNTHESIS; N BOND FORMATION; QUINAZOLINE DERIVATIVES; ACRIDONE ALKALOIDS; SOLVENT; 2-PHENYLQUINAZOLINES; FUNCTIONALIZATION; BENZIMIDAZOLES; AMINATION; OXIDATION;
D O I
10.1016/j.tetlet.2018.05.019
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A single-pot procedure for the synthesis of 2,4-diarylquinazolines is described which involves a silver oxide-mediated C-H activation/C-N bond formation process. The generality of this method with respect to substituent effects is presented along with studies leading to process optimization. Mechanistic investigations provide support for the involvement of radical intermediates in the reaction process. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2368 / 2371
页数:4
相关论文
共 36 条
  • [31] Transformation of 5,5-diaryl-4,5-dihydro-1,2,4-oxadiazoles to 4-arylquinazolines
    Szczepankiewicz, W
    Wagner, P
    Danicki, M
    Suwinski, J
    [J]. TETRAHEDRON LETTERS, 2003, 44 (10) : 2015 - 2017
  • [32] Copper-Catalyzed C(sp3)-C(sp3) Bond Formation Using a Hypervalent Iodine Reagent: An Efficient Allylic Trifluoromethylation
    Wang, Xi
    Ye, Yuxuan
    Zhang, Songnan
    Feng, Jiajie
    Xu, Yan
    Zhang, Yan
    Wang, Jianbo
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (41) : 16410 - 16413
  • [33] Recent developments in the field of quinazoline chemistry
    Witt, A
    Bergman, J
    [J]. CURRENT ORGANIC CHEMISTRY, 2003, 7 (07) : 659 - 677
  • [34] Metal-free intramolecular oxidative decarboxylative amination of primary α-amino acids with product selectivity
    Yan, Yizhe
    Wang, Zhiyong
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (33) : 9513 - 9515
  • [35] A Simple and Efficient Approach to the Synthesis of 2-Phenylquinazolines via sp3 C-H Functionalization
    Zhang, Jintang
    Zhu, Dapeng
    Yu, Chenmin
    Wan, Changfeng
    Wang, Zhiyong
    [J]. ORGANIC LETTERS, 2010, 12 (12) : 2841 - 2843
  • [36] Catalyst-free synthesis of quinazoline derivatives using low melting sugar-urea-salt mixture as a solvent
    Zhang, Zhan-Hui
    Zhang, Xiao-Nan
    Mo, Li-Ping
    Li, Yong-Xiao
    Ma, Fei-Ping
    [J]. GREEN CHEMISTRY, 2012, 14 (05) : 1502 - 1506