Rh(III)-Catalyzed [3+2] Spirocyclization of 2H-Imidazoles with 1,3-Diynes for the Synthesis of Spiro-[imidazole-indene] Derivatives

被引：29
作者：
Luo, Yi [1 ]
Liu, Hao [1 ]
Zhang, Jing [1 ]
Liu, Man [1 ]
Dong, Lin [1 ]
机构：
[1] Sichuan Univ, Sichuan Res Ctr Drug Precis Ind Technol, Key Lab Drug Targeting & Drug Delivery Syst, West China Sch Pharm,Educ Minist, Chengdu 610041, Peoples R China
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 19期
关键词：
CARDIOTONIC AGENTS; ANNULATION; KETIMINES; ACTIVATION;
D O I：
10.1021/acs.orglett.0c02805
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An effective strategy to synthesize spirocyclic compounds, [imidazole-4,1'-indene], has been efficaciously developed relied on Rh(III)-catalyzed [3 + 2] spirocyclization of 2H-imidazoles and 1,3-diynes with excellent chemselectivity and regioselectivity. This protocol shows a straightforward way to construct the versatile spirocyclic compounds with wide functional group compatibility, high atom economy, and diverse functionalization of products.
引用
收藏
页码：7604 / 7608
页数：5
相关论文
共 50 条
  • [41] Cp*Rh(III)-Catalyzed C-H 3,3-Difluoroallylation of Indoles and N-Iodosuccinimide-Mediated Cyclization for the Synthesis of Fluorinated 3,4-Dihydropyrimido-[1,6-a]indol-1(2H)-one Derivatives
    Zhao, Sen
    Li, Chunpu
    Xu, Bin
    Liu, Hong
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (06) : 1549 - 1562
  • [42] Base-promoted synthesis of 1H,3H-pyrrolo[1,2-c]thiazol-3-imine derivatives via [3+2] annulation of 2-alkynylpyrroles with isothiocyanates
    Zhang, Ziyin
    Guo, Biao
    Zhou, Yiming
    Hua, Ruimao
    [J]. TETRAHEDRON, 2016, 72 (47) : 7613 - 7619
  • [43] Enantioselective Synthesis of 1-Aminoindanes via [3+2] Annulation of Aldimines with Alkenes by Scandium-Catalyzed C-H Activation
    Mishra, Aniket
    Cong, Xuefeng
    Nishiura, Masayoshi
    Hou, Zhaomin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (31) : 17468 - 17477
  • [44] Bronsted Acid Catalyzed [3+2]-Cycloaddition of Cyclic Enamides with in Situ Generated 2-Methide-2H-indoles: Enantioselective Synthesis of Indolo[1,2-a]indoles
    Bera, Kalisankar
    Schneider, Christoph
    [J]. ORGANIC LETTERS, 2016, 18 (21) : 5660 - 5663
  • [45] Rhodium(III)-Catalyzed [3+2] Annulation of 5-Aryl-2,3-dihydro-1H-pyrroles with Internal Alkynes through C(sp2)-H/Alkene Functionalization
    Zhou, Ming-Bo
    Pi, Rui
    Hu, Ming
    Yang, Yuan
    Song, Ren-Jie
    Xia, Yuanzhi
    Li, Jin-Heng
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (42) : 11338 - 11341
  • [46] Bronsted Acid Catalyzed [3+2]-Cycloaddition of 2-Vinylindoles with In Situ Generated 2-Methide-2H-indoles: Highly Enantioselective Synthesis of Pyrrolo[1,2-a]indoles
    Bera, Kalisankar
    Schneider, Christoph
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (21) : 7074 - 7078
  • [47] Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles with Internal Alkynes through Dual C(sp2)H Functionalization
    Yang, Yuan
    Zhou, Ming-Bo
    Ouyang, Xuan-Hui
    Pi, Rui
    Song, Ren-Jie
    Li, Jin-Heng
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (22) : 6595 - 6599
  • [48] Rh(III)-Catalyzed C-H Annulation of 3-Aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides with Vinylene Carbonates
    Ittamalla, Chaitanya
    Chary, D. Yogananda
    Balasubramanian, Sridhar
    Reddy, B. V. Subba
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (04)
  • [49] Selective Synthesis of Aminoisoquinolines via Rh(III)-Catalyzed C-H/N-H Bond Functionalization of N-Aryl Amidines with Cyclic 2-Diazo-1,3-diketones
    Zuo, Youpeng
    He, Xinwei
    Ning, Yi
    Wu, Yuhao
    Shang, Yongjia
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21) : 13463 - 13472
  • [50] Asymmetric Diels-Alder Reaction of 2-Arylidene-1,3-indanediones with 2-Vinylindoles Catalyzed by a Sc(OTf)3/Bis(oxazoline) Complex: Enantioselective Synthesis of Tetrahydrocarbazole Spiro Indanedione Derivatives
    Tan Fen
    Chen Jiarong
    Wang Ping
    Xiao Wenjing
    [J]. ACTA CHIMICA SINICA, 2014, 72 (07) : 836 - 840
12345