Palladium-catalyzed [5+2] oxidative annulation of N-Arylhydrazones with alkynes through C-H activation to synthesize Benzo[d][1,2]diazepines

被引:17
|
作者
Asamdi, Manjoorahmed [1 ]
Shaikh, Mohammedumar M. [1 ]
Chauhan, Prakashsingh M. [1 ]
Chikhalia, Kishor H. [2 ]
机构
[1] Gujarat Univ, Dept Chem, Ahmadabad 380009, Gujarat, India
[2] Veer Narmad South Gujarat Univ, Dept Chem, Surat 395007, Gujarat, India
关键词
Pd catalyst; 5+2] annulation; C-H activation; Alkyne; Palladacycle; OH BOND ACTIVATION; STEREOSELECTIVE-SYNTHESIS; ANTI-HIV-1; ACTIVITY; EFFICIENT SYNTHESIS; COUPLING REACTION; TIBO DERIVATIVES; FUNCTIONALIZATION; TOSYLHYDRAZONES; CONSTRUCTION; HETEROCYCLES;
D O I
10.1016/j.tet.2018.05.051
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and novel method using palladium catalyst for the synthesis of benzo[d][1,2]diazepines by [5 + 2] annulation of N-arylhydrazones with alkynes has been developed. This methodology undergoes through eight membered palladacycle serving as a backbone for the formation of C-C/C-N bond to provide benzodiazepine derivatives in moderate to good yield. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3719 / 3727
页数:9
相关论文
共 50 条
  • [31] Synthesis of 1,2′-Spirobi[indene]-1,3-diones by Pd(II)-Catalyzed C-H Activation and Alkynes Annulation Reaction
    Xu, Xuefeng
    Yu, Lintao
    Chang, Mengfan
    Wang, Di
    Shen, Zhi
    Zhang, Xu
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (13) : 2926 - 2932
  • [32] Rhodium(III)-Catalyzed Annulation of 2-Alkenyl Anilides with Alkynes through C-H Activation: Direct Access to 2-Substituted Indolines
    Font, Marc
    Cendon, Borja
    Seoane, Andres
    Luis Mascarenas, Jose
    Gulias, Moises
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (27) : 8255 - 8259
  • [33] Palladium(II)-Catalyzed Oxidative Annulation of 2-Hydroxynaphthalene-1,4-diones and Internal Alkynes via C-H Functionalization
    Sun, Peng
    Yang, Jiaojiao
    Peng, Jinsong
    Mo, Baichuan
    Chen, Xin
    Li, Xiang
    Chen, Chunxia
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (10) : 6761 - 6769
  • [34] Rhodium(III)-Catalyzed [4+3] Annulation of N-Aryl-pyrazolidinones and Propargylic Acetates: Access to Benzo[c][1,2]diazepines
    Li, Tingfang
    Yang, Zi
    Song, Zhenyu
    Chauvin, Remi
    Cui, Xiuling
    ORGANIC LETTERS, 2020, 22 (11) : 4078 - 4082
  • [35] Ru(II)-Catalyzed annulation of benzamidines and alkynes by C-H/N-H activation: a facile synthesis of 1-aminoisoquinolines
    Kaishap, P. P.
    Duarah, G.
    Chetia, D.
    Gogoi, S.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (16) : 3491 - 3498
  • [36] Palladium-catalyzed oxidative C-H bond acylation of N-nitrosoanilines with toluene derivatives: a traceless approach to synthesize N-alkyl-2-aminobenzophenones
    Wu, Yinuo
    Feng, Ling-Jun
    Lu, Xiao
    Kwong, Fuk Yee
    Luo, Hai-Bin
    CHEMICAL COMMUNICATIONS, 2014, 50 (97) : 15352 - 15354
  • [37] Iron-Carbonyl-Catalyzed Redox-Neutral [4+2] Annulation of N-H Imines and Internal Alkynes by C-H Bond Activation
    Jia, Teng
    Zhao, Chongyang
    He, Ruoyu
    Chen, Hui
    Wang, Congyang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (17) : 5268 - 5271
  • [38] Palladium-Catalyzed Oxidative sp2 C-H Bond Acylation with Aldehydes
    Basle, Olivier
    Bidange, Johan
    Shuai, Qi
    Li, Chao-Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (07) : 1145 - 1149
  • [39] Synthesis of Dibenzopyranones through Palladium-Catalyzed Directed C-H Activation/Carbonylation of 2-Arylphenols
    Luo, Shuang
    Luo, Fei-Xian
    Zhang, Xi-Sha
    Shi, Zhang-Jie
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (40) : 10598 - 10601
  • [40] Palladium-Catalyzed Synthesis of Fluorescent Benzo[4,5]imidazo[1,2-a]pyridines through Annulation Reaction of Benzimidazoles and Alkynyl Bromides with Internal Alkynes
    Chen, Xin
    Sun, Peng
    Mo, Baichuan
    Chen, Chunxia
    Peng, Jinsong
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01) : 352 - 366