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
  • [41] Palladium-catalyzed cyclization of 6-aminohex-1-yne
    Müller, TE
    Berger, M
    Grosche, M
    Herdtweck, E
    Schmidtchen, FP
    ORGANOMETALLICS, 2001, 20 (21) : 4384 - 4393
  • [42] Photoredox-catalyzed cascade [2+2+1] cyclization of 1,6-enynes with thiols
    Meng, Zhe
    Shi, Min
    Wei, Yin
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (12) : 3442 - 3450
  • [43] Palladium-Catalyzed Hydroboration/Cyclization of 1,n-Dienes
    Kanno, Shota
    Kakiuchi, Fumitoshi
    Kochi, Takuya
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (04): : 2621 - 2630
  • [44] Palladium-Catalyzed Hydrocarbonylative Cyclization of 1,5-Dienes
    Zou, Suchen
    Gao, Bao
    Huang, Yao
    Zhang, Tianze
    Huang, Hanmin
    ORGANIC LETTERS, 2019, 21 (16) : 6333 - 6336
  • [45] Palladium-catalyzed cyclization of 1-alkynyl-8-iodonaphthalene and double isocyanides for the synthesis of acenaphtho[1,2-b]pyrroles
    Shangfeng Ren
    Keke Huang
    Jin-Biao Liu
    Lianpeng Zhang
    Min Hou
    Guanyinsheng Qiu
    Chinese Chemical Letters, 2022, 33 (11) : 4870 - 4873
  • [46] Palladium-catalyzed cyclization of 1-alkynyl-8-iodonaphthalene and double isocyanides for the synthesis of acenaphtho[1,2-b]pyrroles
    Ren, Shangfeng
    Huang, Keke
    Liu, Jin-Biao
    Zhang, Lianpeng
    Hou, Min
    Qiu, Guanyinsheng
    CHINESE CHEMICAL LETTERS, 2022, 33 (11) : 4870 - 4873
  • [47] Synthesis of trifluoromethyl-group-containing cyclopentadienones by the palladium-catalyzed [2+2+1] cycloaddition of aryl- and trifluoromethyl-group substituted internal alkynes and carbon monoxide
    Murakami, Shogo
    Sonehara, Taro
    Iwakami, Kousuke
    Tsuji, Hiroaki
    Kawatsura, Motoi
    TETRAHEDRON LETTERS, 2019, 60 (08) : 598 - 601
  • [48] Palladium-Catalyzed Synthesis of 2-Aminobenzoxazinones by Aerobic Oxidative Coupling of Anthranilic Acids and Isocyanides
    Vlaar, Tjostil
    Orru, Romano V. A.
    Maes, Bert U. W.
    Ruijter, Eelco
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20): : 10469 - 10475
  • [49] Palladium-Catalyzed Tandem C(sp3)-H Insertion Cyclization of 2-(2-Vinylarene)acetonitriles with Isocyanides to Access Naphthalen-2-amines
    Lin, Huishu
    Pan, Yongzhou
    Fu, Jinping
    Yi, Yi
    Tang, Haitao
    Pan, Yingming
    Yu, Wanguo
    Wang, Xu
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (17): : 12409 - 12420
  • [50] Palladium-Catalyzed [2+2+1] Oxidative Annulation of 4-Hydroxycoumarins with Unactivated Internal Alkynes: Access to Spiro Cyclopentadiene-Chroman-2,4-dione Complexes
    Peng, Shiyong
    Gao, Tao
    Sun, Shaofa
    Peng, Yanhong
    Wu, Minghu
    Guo, Haibing
    Wang, Jian
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (2-3) : 319 - 324