Palladium-Catalyzed Imidoylation-Triggered [2+2+1] Cyclization of Internal Alkyne with Isocyanides

被引:15
|
作者
Huang, Keke [1 ,2 ]
Liu, Jin-Biao [1 ]
Chen, Zhi-Feng [2 ]
Wang, Yu-Chao [2 ]
Yadav, Sarita [2 ]
Qiu, Guanyinsheng [2 ]
机构
[1] Jiangxi Univ Sci & Technol, Sch Met & Chem Engn, Ganzhou 341000, Peoples R China
[2] Jiaxing Univ, Coll Biol Chem Sci & Engn, Jiaxing 314001, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; CASCADE REACTIONS; MIGRATORY INSERTION; 4+1 CYCLOADDITION; ISONITRILES; MULTICOMPONENT; ACTIVATION; KETENIMINE; PROGRESS; CONSTRUCTION;
D O I
10.1021/acs.orglett.0c02019
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this work, a palladium-catalyzed [2 + 2 + 1] cyclization of internal alkynes with double isocyanides is described. This facile procedure is efficient for synthesizing various pyrrolo-[3,2-c]quinolin-2-amines. The reaction worked well with a broad reaction scope. In the process, it is believed that sequential double isocyanide insertion, 6-exo-dig cyclization of alkyne, and addition of an imino group are involved.
引用
收藏
页码:5931 / 5935
页数:5
相关论文
共 50 条
  • [1] Palladium-catalyzed concerted [4+1] cyclization of prop-2-yn-1-ones and isocyanides
    Yingying Shan
    Lei Su
    Dianpeng Chen
    Min Yang
    Wenlin Xie
    Guanyinsheng Qiu
    ChineseChemicalLetters, 2021, 32 (01) : 437 - 440
  • [2] Palladium-catalyzed concerted [4+1] cyclization of prop-2-yn-1-ones and isocyanides
    Shan, Yingying
    Su, Lei
    Chen, Dianpeng
    Yang, Min
    Xie, Wenlin
    Qiu, Guanyinsheng
    CHINESE CHEMICAL LETTERS, 2021, 32 (01) : 437 - 440
  • [3] Iodomethane in C1 chemistry: application in palladium-catalyzed [2+2+1] annulation
    Zhang, Jin-Ke
    Fang, Yu-Chen
    Chen, Jia-He
    Shan, Jing
    Bai, Mei
    Huang, Qiang
    Chen, Yong-Zheng
    Han, Wen-Yong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (16) : 3204 - 3208
  • [4] Aziridine used as a vinylidene unit in palladium-catalyzed [2+2+1] domino annulation
    Zhu, Wen-Qing
    Zhang, Zi-Wei
    Han, Wen-Yong
    Fang, Yu-Chen
    Yang, Ping
    Li, Lin-Qiang
    Chen, Yong-Zheng
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (13): : 3413 - 3420
  • [5] Synthesis of 2-aminoquinolines via palladium-catalyzed intermolecular oxidative cyclization of 2-vinylanilines with isocyanides
    Zheng, Qiang
    Ding, Qiuping
    Wang, Cong
    Chen, Wenfan
    Peng, Yiyuan
    TETRAHEDRON, 2016, 72 (07) : 952 - 958
  • [6] Palladium-catalyzed Decarboxylative [4+1] Cyclization of γ-Methylidene-δ-valerolactones with Isocyanides
    Park, Soyoung
    Shintani, Ryo
    Hayashi, Tamio
    CHEMISTRY LETTERS, 2009, 38 (03) : 204 - 205
  • [7] Palladium-Catalyzed [2+2+1] Spiroannulation via Alkyne-Directed Remote C-H Arylation and Subsequent Arene Dearomatization
    Zuo, Zhijun
    Wang, Jing
    Liu, Jingjing
    Wang, Yaoyu
    Luan, Xinjun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (02) : 653 - 657
  • [8] A convenient regioselective synthesis of cyclopentadienones via palladium-catalyzed [2+2+1] cyclocarbonylation of alkynes
    Xu, Yanli
    Zhao, Jinwu
    Chen, Huoji
    Wu, Wanqing
    Jiang, Huanfeng
    CHEMICAL COMMUNICATIONS, 2014, 50 (19) : 2488 - 2490
  • [9] Palladium-catalyzed carbonylative cyclization of 1-iodo-2-alkenylbenzenes
    Negishi, E
    Coperet, C
    Ma, SM
    Mita, T
    Sugihara, T
    Tour, JM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (25) : 5904 - 5918
  • [10] Palladium-Catalyzed [2+2+1] Annulation of Alkyne-Tethered Aryl Iodides with Diaziridinone: Synthesis of 3,4-Fused Tricyclic Indoles
    Zhang, Lei
    Chen, Junyu
    Zhong, Tianshuo
    Zheng, Xiangyun
    Zhou, Jian
    Jiang, Xinpeng
    Yu, Chuanming
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (16): : 10823 - 10834