Rhodium-catalyzed benzoisothiazole synthesis by tandem annulation reactions of sulfoximines and activated olefins

被引:24
|
作者
Li, Yang [1 ]
Dong, Lin [1 ]
机构
[1] Sichuan Univ, West China Sch Pharm, Educ Minist, Key Lab Drug Targeting & Drug Delivery Syst, Chengdu 610041, Sichuan, Peoples R China
关键词
C-BOND FORMATION; NH-SULFOXIMINES; OXIDATIVE OLEFINATION; BENZOIC-ACIDS; RING-SYSTEMS; ONE-POT; ALKYNES; 1,2-BENZOTHIAZINES; FUNCTIONALIZATION; STRATEGIES;
D O I
10.1039/c7ob02586f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium(III)-catalyzed N-directed ortho C-H activation reactions have been developed for the synthesis of unique heterocyclic benzoisothiazoles. Herein, this novel tandem annulation approach can efficiently construct benzoisothiazole compounds from free NH-sulfoximines and alkenes via C-H activation, olefination and subsequent intramolecular aza-Michael cyclization.
引用
收藏
页码:9983 / 9986
页数:4
相关论文
共 50 条
  • [1] Synthesis of Indenyl Triazenes by Rhodium-Catalyzed Annulation Reactions
    Bormann, Carl T.
    Abela, Florian G.
    Scopelliti, Rosario
    Fadaei-Tirani, Farzaneh
    Severin, Kay
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (14) : 2130 - 2139
  • [2] Rhodium-Catalyzed Oxidative Annulation of Sulfoximines and Alkynes as an Approach to 1,2-Benzothiazines
    Dong, Wanrong
    Wang, Long
    Parthasarathy, Kanniyappan
    Pan, Fangfang
    Bolm, Carsten
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (44) : 11573 - 11576
  • [3] Rhodium-catalyzed amination reactions of olefins and aldehydes.
    Beller, M
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U551 - U552
  • [4] Rhodium-Catalyzed Tandem Annulation Reactions of 7-Azaindoles with Electron-Deficient Olefins via Double C-H Activation
    Li, Shuai-Shuai
    Lin, Hui
    Liu, Chen-Fei
    Xia, Ying-Qi
    Zhang, Xiao-Mei
    Dong, Lin
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (10) : 1595 - 1601
  • [5] Synthesis of Polysubstituted Phenols by Rhodium-Catalyzed C-H/Diazo Coupling and Tandem Annulation
    Liu, Min
    Yan, Kelu
    Wen, Jiangwei
    Li, Xue
    Wang, Xiaoyu
    Lu, Fengjie
    Wang, Xiu
    Wang, Hua
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (07) : 1855 - 1860
  • [6] Synthesis of Phthalides through Tandem Rhodium-Catalyzed C-H Olefination and Annulation of Benzamides
    Mishra, Neeraj Kumar
    Park, Jihye
    Choi, Miji
    Sharma, Satyasheel
    Jo, Hyeim
    Jeong, Taejoo
    Han, Sangil
    Kim, Saegun
    Kim, In Su
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (18) : 3076 - 3083
  • [7] Regio- and diastereoselective tandem rhodium-catalyzed allylic alkylation Pauson-Khand annulation reactions
    Evans, PA
    Robinson, JE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) : 4609 - 4610
  • [8] Highly enantioselective rhodium-catalyzed [4+2] annulation reactions
    Tanaka, Ken
    CHIMICA OGGI-CHEMISTRY TODAY, 2006, 24 (04) : 20 - +
  • [9] Theoretical elucidation of the rhodium-catalyzed [4+2] annulation reactions
    Geng, Cai-Yun
    Li, Ji-Lai
    Huang, Xu-Ri
    Liu, Hui-Ling
    Ll, Zhuo
    Sun, Chia-Chung
    JOURNAL OF COMPUTATIONAL CHEMISTRY, 2008, 29 (05) : 686 - 693
  • [10] Rhodium-catalyzed direct synthesis of unprotected NH-sulfoximines from sulfoxides
    Miao, Jinmin
    Richards, Nigel G. J.
    Ge, Haibo
    CHEMICAL COMMUNICATIONS, 2014, 50 (68) : 9687 - 9689