Sc(OTf)3-Catalyzed Tunable Thio-(3+3) Annulation Reactions of Indoline-2-thiones with α-Benzylidene-β-tetralones

被引：0
|
作者：
Jiang, Yan [1 ]
Ma, Hao-Jie [1 ]
Zhai, Chen-Ying [1 ]
Wang, Xue-Long [1 ]
Yang, Yi [1 ]
机构：
[1] Sichuan Univ Sci & Engn, Key Lab Green Chem Sichuan Inst Higher Educ, Coll Chem & Environm Engn, 519 Huixing Rd, Zigong, Sichuan, Peoples R China
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 14卷 / 02期
关键词：
indoline-2-thiones; tetralone; (3+3) annulation; sulfur-containing heterocycles; thiazine; MEDICINAL CHEMISTRY; INDOLE; DERIVATIVES; INSIGHT;
D O I：
10.1002/ajoc.202400452
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Sc(OTf)3-catalyzed tunable thio-Michael addition/nucleophilic addition/dehydration reaction of indoline-2-thiones with alpha-benzylidene-beta-tetralones was realized, leading to biologically important tetrahydrobenzo[7,8]isothiochromeno[3,4-b]indoles and thiazino[3,2-a]indoles in moderate to good yields. Moreover, by extending the reaction time, the dehydrogenated cycloadducts dihydrobenzo[7,8]isothiochromeno[3,4-b]indoles were also obtained from the reaction of indoline-2-thiones with alpha-benzylidene-beta-tetralones.
引用
收藏
页数：5
相关论文
共 50 条
  • [31] Rhodium catalyzed allene amidation: a facile entry into 2-amidoallylcations for unusual [3+3] annulation reactions
    Stoll, Armin H.
    Blakey, Simon B.
    CHEMICAL SCIENCE, 2011, 2 (01) : 112 - 116
  • [32] Fe(OTf)3-catalyzed annulation of α,β-unsaturated ketoxime acetates with enaminones for the synthesis of functionalized 2,4-diarylpyridines
    Hu, Xing-Mei
    Yang, Jing
    Yang, Jia-Ming
    Shao, Bi-Na
    Huang, Rong
    Yan, Sheng-Jiao
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (17) : 4298 - 4304
  • [33] Approach to Trisubstituted 3-Aminopyrrole Derivatives by Yb(OTf)3-Catalyzed [4+1] Annulation of 2-Azadiene with Me3SiCN
    Sasada, Toshiaki
    Sawada, Takuya
    Ikeda, Reiko
    Sakai, Norio
    Konakahara, Takeo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (22) : 4237 - 4244
  • [34] Sc(OTf)3-catalyzed cyclocondensation of 2-propylresorcinol with diethoxymethane.: Formation and fragmentation of resorcin[n]arenes
    Morikawa, O
    Yanagimoto, M
    Sakakibara, H
    Kobayashi, K
    Konishi, H
    TETRAHEDRON LETTERS, 2004, 45 (29) : 5731 - 5734
  • [35] Sc(OTf)3/BF3•OEt2-Catalyzed Annulation of 3-Formylchromones with Functionalized Alkenes: Access to Diverse 2-Hydroxybenzophenones
    Sultana, Sabera
    Rubio, Peter Yuosef M.
    Khanal, Hari Datta
    Lee, Yong Rok
    ORGANIC LETTERS, 2022, 24 (24) : 4360 - 4364
  • [36] AlCl3-mediated ring-opening reactions of indoline-2-thiones with acyl cyclopropanes, bi-cyclopropanes and spirocyclic cyclopropanes
    Ma, Hao-Jie
    Gao, Ke
    Wang, Xue-Long
    Zeng, Jun-Yi
    Yang, Yi
    Jiang, Yan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (31) : 6312 - 6316
  • [37] Hg(OAc)2•0.1Sc(OTf)3-catalyzed cycloisomerization of 2-(4-pentynyl)furan
    Yamamoto, Hirofumi
    Sasaki, Ikuo
    Imagawa, Hiroshi
    Nishizawa, Mugio
    ORGANIC LETTERS, 2007, 9 (07) : 1399 - 1402
  • [38] Calix[6]arene derivatives bearing sulfonate and alkyl groups as surfactants in Sc(OTf)3-catalyzed Mukaiyama aldol reactions in water
    Tian, HY
    Chen, YJ
    Wang, D
    Zeng, CC
    Li, CJ
    TETRAHEDRON LETTERS, 2000, 41 (15) : 2529 - 2532
  • [39] Sc(OTf)3-catalyzed effcient synthesis of β,β-bis(indolyl) ketones by the double indolylation of acetic acid 2-methylene-3-oxobutyl ester
    Ma, SM
    Yu, SC
    Peng, ZH
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (10) : 1933 - 1936
  • [40] Sc(OTf)3-Catalyzed Diastereoselective Formal [3+2] Cycloaddition Reactions of Alkynylcyclopropane Ketones with Electron-Rich Aromatic Aldehydes To Yield 2,5-trans-Tetrahydrofurans
    Zhang, Chi
    Xu, Muyun
    Ren, Jun
    Wang, Zhongwen
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (14) : 2467 - 2478
12345