Rhodium(III)-catalyzed C-H amination of 2-arylquinazolin-4(3H)-one with N-alkyl-O-benzoyl-hydroxylamines

被引：18
作者：
Zhang, Yuanguang [1 ]
Huang, Jiang [1 ]
Deng, Zhihong [1 ]
Mao, Xunchun [1 ]
Peng, Yiyuan [1 ]
机构：
[1] Jiangxi Normal Univ, Jiangxi Prov Key Lab Green Chem, Minist Educ, Key Lab Funct Small Organ Mol, Nanchang 330022, Jiangxi, Peoples R China
来源：
TETRAHEDRON | 2018年 / 74卷 / 19期
基金：
中国国家自然科学基金;
关键词：
C-H activation; Amination; Rh-catalyzed; 2-arylquinazolin-4(3H)-one; CATALYZED ELECTROPHILIC AMINATION; DIRECTING-GROUP; BOND ACTIVATION; AMIDATION; ARENES; DERIVATIVES; QUINAZOLINONE; AZIDES; ROUTE; SITE;
D O I：
10.1016/j.tet.2018.03.051
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-benzoate alkylamines were used as the aminating agents, a efficient Rh-catalyzed ortho C-H amination of 2-arylquinazolin-4(3H)-one has been reported. The reactions exhibit high efficient and good functional group tolerance. Exclusive 2,6-bis-aminated product and good to excellent yields were obtained under mild reaction conditions. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2330 / 2337
页数：8
相关论文
共 50 条
  • [41] Rhodium(III)-Catalyzed Regioselective C-H Annulation and Alkenylation of 2-Pyridones with Terminal Alkynes
    Li, Jiajie
    Xu, Xin
    Luo, Zhenli
    Yao, Zhen
    Yang, Ji
    Zhang, Xin
    Xu, Lijin
    Wang, Peng
    Shi, Qian
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (07) : 1264 - 1270
  • [42] A [4+1] Cyclative Capture Approach to 3H-Indole-N-oxides at Room Temperature by Rhodium(III)-Catalyzed C-H Activation
    Yang, Yaxi
    Wang, Xuan
    Li, Yuanchao
    Zhou, Bing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (51) : 15400 - 15404
  • [43] A new library of 4(3H)- and 4,4′(3H,3H′)-quinazolinones and 2-(5-alkyl-1,2,4-oxadiazol-3-yl)quinazolin-4(3H)-one obtained from diaminoglyoxime
    Moghimi, Abolghasem
    Khanmiri, Rahim Hosseinzadeh
    Omrani, Ismail
    Shaabani, Ahmad
    TETRAHEDRON LETTERS, 2013, 54 (30) : 3956 - 3959
  • [44] Rh[III]-Catalyzed Direct C-H Amination Using N-Chloroamines at Room Temperature
    Grohmann, Christoph
    Wang, Honggen
    Glorius, Frank
    ORGANIC LETTERS, 2012, 14 (02) : 656 - 659
  • [45] Rhodium(III)-Catalyzed ortho Alkenylation of N-Phenoxyacetamides with N-Tosylhydrazones or Diazoesters through C-H Activation
    Hu, Fangdong
    Xia, Ying
    Ye, Fei
    Liu, Zhenxing
    Ma, Chen
    Zhang, Yan
    Wang, Jianbo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (05) : 1364 - 1367
  • [46] Copper (II)-supported polyethylenimine-functionalized magnetic graphene oxide as a catalyst for the green synthesis of 2-arylquinazolin-4(3H)-ones
    Mohammad Hosein Sayahi
    Saeed Bahadorikhalili
    Seyyed Jafar Saghanezhad
    Mohammad Mahdavi
    Research on Chemical Intermediates, 2018, 44 : 5241 - 5253
  • [47] Rhodium(III)-Catalyzed Synthesis of Quinazolin-4(3H)-ones with N-Methoxyamides as Synthesis Reagents
    Zhou, Guanyu
    Huang, Zhibin
    Xu, Xu
    Fang, Zhang
    Huang, Pengcheng
    Deng, Zefeng
    Li, Bao
    Zhao, Yingsheng
    SYNTHESIS-STUTTGART, 2022, 54 (14): : 3298 - 3306
  • [48] Rhodium(I)-Catalyzed C2-Selective Decarbonylative C-H Alkylation of Indoles with Alkyl Carboxylic Acids and Anhydrides
    Yu, Haiyang
    Zhao, Haoqiang
    Xu, Xin
    Zhang, Xin
    Yu, Zexin
    Li, Lingchao
    Wang, Peng
    Shi, Qian
    Xu, Lijin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (04) : 879 - 885
  • [49] Rhodium(III)-Catalyzed C-C and C-O Coupling of Quinoline N-Oxides with Alkynes: Combination of C-H Activation with O-Atom Transfer
    Zhang, Xueyun
    Qi, Zisong
    Li, Xingwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (40) : 10794 - 10798
  • [50] C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation
    Song, Guoyong
    Wang, Fen
    Li, Xingwei
    CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) : 3651 - 3678
12345