4-Dimethylaminopyridine-catalyzed [3+3] spiroannulation reactions of isatin-derived Morita-Baylis-Hillman carbonates with indoline-2-thiones

被引：9
|
作者：
Geng, Congcong [1 ]
Wei, Xingfu [1 ]
Xu, Yongqiang [1 ]
Liu, Jianhui [1 ]
Peng, Lizeng [2 ]
Wang, Baomin [1 ]
机构：
[1] Dalian Univ Technol, Dept Pharmaceut Sci, State Key Lab Fine Chem, Dalian 116024, Peoples R China
[2] Shandong Acad Agr Sci, Jinan 250100, Peoples R China
来源：
TETRAHEDRON LETTERS | 2022年 / 102卷
关键词：
Spiroannulations; DMAP; Morita -Baylis -Hillman carbonates; Sulfur heterocycles; ANNULATED SULFUR HETEROCYCLES; STEREOSELECTIVE-SYNTHESIS; CONSTRUCTION; DERIVATIVES; ALKYLATION; ACCESS; THIOPYRANO; SKELETONS; OXINDOLES; ADDUCTS;
D O I：
10.1016/j.tetlet.2022.153950
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
DMAP-catalyzed diastereoselective [3 + 3] spiroannulations of isatin-derived Morita-Baylis-Hillman car-bonates with indoline-2-thiones were achieved. A series of bisindole-annulated thiopyran frameworks were synthesized in good yields with good diastereoselectivities. The strategy developed in this paper offered a novel way for the synthesis of valuable indole-annulated sulfur heterocycle derivatives which might be beneficial in organic synthesis and medicinal chemistry. (c) 2022 Elsevier Ltd. All rights reserved.
引用
收藏
页数：4
相关论文
共 50 条
  • [41] 4-(Dimethylamino)pyridine-Catalyzed (3+2) Annulation of Pyrazoledione-Derived Morita-Baylis-Hillman Carbonates with 2-Arylideneindane-1,3-Diones: An Access to Dispirocyclic Compounds
    Liao, Jianning
    Xu, Jiaqing
    Wu, Yongjun
    Hou, Yuxia
    Guo, Hongchao
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (06) : 1074 - 1079
  • [42] Access to thiopyrano[2,3-b] indole via tertiary amine-catalyzed formal (3+3) annulations of β′-acetoxy allenoates with indoline-2-thiones
    Ni, Chunjie
    Zhang, Yuwen
    Hou, Yading
    Tong, Xiaofeng
    CHEMICAL COMMUNICATIONS, 2017, 53 (17) : 2567 - 2570
  • [43] Highly Regio- and Diastereoselective Construction of Spirocyclopenteneoxindoles through Phosphine-Catalyzed [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Isatylidene Malononitriles
    Deng, Hong-Ping
    Wei, Yin
    Shi, Min
    ORGANIC LETTERS, 2011, 13 (13) : 3348 - 3351
  • [44] Phosphine-catalyzed [3+2] cycloaddition of Morita-Baylis-Hillman carbonates to isothiocyanates in the synthesis of adamantane-containing trisubstituted aminothiophenes
    Zenkov, I. S.
    Abel, A. S.
    Averin, A. D.
    Butov, G. M.
    Beletskaya, I. P.
    RUSSIAN CHEMICAL BULLETIN, 2021, 70 (05) : 880 - 884
  • [45] Amine-Catalyzed Tandem Reactions of Morita-Baylis-Hillman Acetates with Isatins: Facile Synthesis of 3-Hydroxyoxindoles
    Chen, Rongshun
    Fan, Xia
    Xu, Zhaozhong
    He, Zhengjie
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (41) : 6154 - 6159
  • [46] A Highly Regio- and Diastereoselective Phosphane-Catalyzed [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Cyclic N-Acyl Ketimines
    Yang, Li-Jun
    Cai, Hua
    Nie, Jing
    Ma, Jun-An
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (20) : 4434 - 4442
  • [47] Construction of polycyclic spirooxindoles through [3+2] annulations of Morita-Baylis-Hillman carbonates and 3-nitro-7-azaindoles
    Wang, Kai-Kai
    Du, Wei
    Zhu, Jin
    Chen, Ying-Chun
    CHINESE CHEMICAL LETTERS, 2017, 28 (03) : 512 - 516
  • [48] Highly regioselective synthesis of 3-alkylthio-2-oxindoles via DABCO-catalyzed allylic α-substitution of Morita-Baylis-Hillman carbonates of isatins with various thiols
    Liu, Xiong-Wei
    Han, Wen-Yong
    Liu, Xiong-Li
    Zhou, Ying
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    TETRAHEDRON, 2014, 70 (48) : 9191 - 9197
  • [49] Synthesis of 3-(β, δ-Disubstituted) allylidene-2-oxindoles by SN2′ Reaction of Phosphorous Ylides with Carbonates of Isatin-derived Moritas-Baylis-Hillman Adducts
    Kim, Su Yeon
    Lee, Sangku
    Kim, Gieun
    Min, Beom Kyu
    Kim, Jae Nyoung
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2017, 38 (09) : 1097 - 1100
  • [50] Substrate-controlled [4+1] and [3+2] annulations of ninhydrin-derived Morita-Baylis-Hillman carbonates to access polysubstituted furans and cyclopentenes
    Wang, Kai-Kai
    Li, Yan-Li
    Li, Ya-Fei
    Yao, Wei-Wei
    Li, Lan-Xin
    He, Xiao-Long
    Chen, Rongxiang
    CHEMICAL COMMUNICATIONS, 2024, 60 (27) : 3717 - 3720
12345