AlCl3-mediated ring-opening reactions of indoline-2-thiones with acyl cyclopropanes, bi-cyclopropanes and spirocyclic cyclopropanes

被引：7
作者：
Ma, Hao-Jie [1 ]
Gao, Ke [1 ]
Wang, Xue-Long [1 ]
Zeng, Jun-Yi [1 ]
Yang, Yi [1 ]
Jiang, Yan [1 ]
机构：
[1] Sichuan Univ Sci & Engn, Sch Chem & Environm Engn, Zigong 643000, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 31期
关键词：
DONOR-ACCEPTOR CYCLOPROPANES;
D O I：
10.1039/d3ob00909b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
AlCl3-mediated nucleophilic ring-opening reactions of indoline-2-thiones with various acyl cyclopropanes, bi-cyclopropanes and spirocyclic cyclopropanes were investigated. A series of ketones functionalized with indolylthio groups were synthesized in yields ranging from moderate to good. Moreover, chemical transformations of 4-indolylthio butan-1-ones to dihydro-2H-thiepino[2,3-b]indoles and sulfone were carried out to further expand both synthetic utility and structural complexity.
引用
收藏
页码：6312 / 6316
页数：5
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  • [1] Donor-Acceptor Cyclopropanes: Activation Enabled by a Single, Vinylogous Acceptor
    Ahlburg, Nils L.
    Hergert, Oliver
    Jones, Peter G.
    Werz, Daniel B.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (01)
  • [2] 4-(Dimethylamino)Pyridinium Azide in Protic Ionic Liquid Media as a Stable Equivalent of Hydrazoic Acid
    Andreev, Ivan A.
    Boichenko, Maksim A.
    Ratmanova, Nina K.
    Ivanova, Olga A.
    Levina, Irina I.
    Khrustalev, Victor N.
    Sedov, Igor A.
    Trushkov, Igor, V
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (14) : 2403 - 2415
  • [3] Photoredox Generation of Isothiouronyl Radical Cations: A New Platform in Covalent Radical Catalysis
    Archer, Gaetan
    Cavalere, Pierre
    Medebielle, Maurice
    Merad, Jeremy
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (32)
  • [4] Exploiting Heavier Organochalcogen Compounds in Donor-Acceptor Cyclopropane Chemistry
    Augustin, Andre U.
    Werz, Daniel B.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2021, 54 (06) : 1528 - 1541
  • [5] Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters
    Bitai, Jacqueline
    Nimmo, Alastair J.
    Slawin, Alexandra M. Z.
    Smith, Andrew D.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (25)
  • [6] Ring Opening of Donor-Acceptor Cyclopropanes with N-Nucle-ophiles
    Budynina, Ekaterina M.
    Ivanov, Konstantin L.
    Sorokin, Ivan D.
    Melnikov, Mikhail Ya.
    [J]. SYNTHESIS-STUTTGART, 2017, 49 (14): : 3035 - 3068
  • [7] Intramolecular donor-acceptor cyclopropane ring-opening cyclizations
    Cavitt, Marchello A.
    Phun, Lien H.
    France, Stefan
    [J]. CHEMICAL SOCIETY REVIEWS, 2014, 43 (03) : 804 - 818
  • [8] Photoinduced Cascade Difluoroalkylative Ring-Opening of Vinyl Cyclopropanes
    Chandu, Palasetty
    Srinivasu, Vinjamuri
    Gupta, Surbhi
    Sureshkumar, Devarajulu
    [J]. ORGANIC LETTERS, 2023, 25 (16) : 2857 - 2862
  • [9] Palladium-Catalyzed Intermolecular Asymmetric Dearomative Annulation of Phenols with Vinyl Cyclopropanes
    Chu, Wen-Dao
    Liang, Tian -Tian
    Ni, Hao
    Dong, Zhi-Hong
    Shao, Zhihui
    Liu, Yong
    He, Cheng-Yu
    Bai, Ruopeng
    Liu, Quan-Zhong
    [J]. ORGANIC LETTERS, 2022, 24 (27) : 4865 - 4870
  • [10] 3,4-Annulated Indoles via Tandem Cyclopropane Ring-Opening/ Conia-ene and Michael Addition/Conia-ene Reactions
    Cochrane, Shane R.
    Kerr, Michael A.
    [J]. ORGANIC LETTERS, 2022, 24 (30) : 5509 - 5512
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