A Cascade Synthesis of Furo-Pyrrolo-Pyridines via Pd(II)-Catalyzed Dual N-H/C Annulative-Cyclization

被引:2
|
作者
Nath Dhara, Hirendra [1 ]
Manna, Supriya [1 ]
Patel, Bhisma K. [1 ]
机构
[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India
关键词
Annulations; Fused heterocycles; Furo-pyrrolo-pyridines; Nitrile-triggered; Pd(II)-catalyst; 3-COMPONENT SYNTHESIS; CATALYZED ANNULATION; BETA-KETODINITRILES; ALKYNES; DISCOVERY; NITRILES; CONSTRUCTION; HETEROCYCLES; DERIVATIVES; POTENT;
D O I
10.1002/chem.202403470
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Pd(II)-catalyzed non-template synthesis of furo[2,3-b]pyrrolo[2,3-d]pyridines from beta-ketodinitriles and buta-1,3-diynes has been accomplished via dual annulative cyclization. The participation of both the nitrile (-CN) groups led to the concurrent construction of three heterocycles viz. furan, pyrrole, and pyridine forming C-C, C=C, C-O, C-N, and C=N bonds in one pot. The synthetic utility of the protocol was further demonstrated through a few post-synthetic manipulations.
引用
收藏
页数:8
相关论文
共 50 条
  • [31] Synthesis of Alkyl-Substituted Pyridines by Directed Pd(II)-Catalyzed C-H Activation of Alkanoic Amides
    Hu, Peng
    Bach, Thorsten
    SYNLETT, 2015, 26 (20) : 2853 - 2857
  • [32] Ruthenium-Catalyzed Synthesis of Macrocyclic Isoquinolines and Isoquinolones via a C-H/N-H Annulations Reaction
    Gurumurthy, Palanivelu
    Raja, Rajini
    Arumugam, Natarajan
    Almansour, Abdulrahman I.
    Kumar, Raju Suresh
    Perumal, Karthikeyan
    Parthasarathy, Kanniyappan
    CHEMISTRYSELECT, 2023, 8 (32):
  • [33] Access to Cycloalkeno[c]-Fused Pyridines via Pd-Catalyzed C(sp2)-H Activation and Cyclization of N-Acetyl Hydrazones of Acylcycloalkenes with Vinyl Azides
    Nie, Biao
    Wu, Wanqing
    Ren, Qingyun
    Wang, Zhongqing
    Zhang, Ji
    Zhang, Yingjun
    Jiang, Huanfeng
    ORGANIC LETTERS, 2020, 22 (20) : 7786 - 7790
  • [34] Modular Synthesis of Quinazolinone-Fused Phenanthridinones by a Palladium-Catalyzed Cascade C-H/N-H Arylation Process
    Yu, Yanhan
    Yue, Yixia
    Wang, Deqiang
    Li, Xue
    Chen, Chunxia
    Peng, Jinsong
    SYNTHESIS-STUTTGART, 2016, 48 (22): : 3941 - 3950
  • [35] Pd-Catalyzed Dual C-H Activation/Cyclization: Convergent and Divergent Synthesis of 1-Azahelicenes
    Xu, Yi-Xin
    Liang, Yu-Qing
    Liu, Wei-Ming
    Fang, Hui-Kang
    Li, Hong-Kun
    Ji, Shun-Jun
    Cai, Zhong-Jian
    ORGANIC LETTERS, 2024, 26 (42) : 9005 - 9010
  • [36] Synthesis of substituted 2H-Chromenes via Pd-catalyzed C-H activation and thermal cyclization
    Maikhuri, Vipin K.
    Verma, Vineet
    Mathur, Divya
    Prasad, Ashok K.
    Khatri, Vinod
    CARBOHYDRATE RESEARCH, 2024, 536
  • [37] Convenient synthesis of N-1-alkyl benzimidazoles via Pd catalyzed C-N bond formation and cyclization
    Bie, Fusheng
    Yao, Yongfeng
    Cao, Han
    Shi, Yijun
    Yan, Peng
    Ma, Jie
    Han, Ying
    Liu, Xuejing
    SYNTHETIC COMMUNICATIONS, 2021, 51 (15) : 2387 - 2396
  • [38] One-pot cascade synthesis of N-methoxyisoquinolinediones via Rh(III)-catalyzed carbenoid insertion C-H activation/cyclization
    Shi, Jingjing
    Zhou, Jie
    Yan, Yunnan
    Jia, Jinlong
    Liu, Xuelei
    Song, Huacan
    Xu, H. Eric
    Yi, Wei
    CHEMICAL COMMUNICATIONS, 2015, 51 (04) : 668 - 671
  • [39] Palladium catalyzed synthesis of sugar-fused indolines via C(sp2)-H/N-H activation
    Verma, Ashish Kumar
    Chennaiah, Ande
    Dubbu, Sateesh
    Vankar, Yashwant D.
    CARBOHYDRATE RESEARCH, 2019, 473 : 57 - 65
  • [40] Versatile synthesis of functionalized β- and γ-carbolines via Pd-catalyzed C-H addition to nitriles/cyclization sequences
    Wang, Ting-Ting
    Zhang, Di
    Liao, Wei-Wei
    CHEMICAL COMMUNICATIONS, 2018, 54 (16) : 2048 - 2051