Three-component synthesis of 1,4-benzothiazines via iodide-catalyzed aerobic C-H sulfuration with elemental sulfur

被引:17
作者
Jiang, Jingjing [1 ]
Tuo, Xiaotong [1 ]
Fu, Zhuquan [1 ]
Huang, Huawen [1 ]
Deng, Guo-Jun [1 ]
机构
[1] Xiangtan Univ, Coll Chem, Key Lab Green Organ Synth & Applicat Hunan Prov, Key Lab Environm Friendly Chem & Applicat,Minist, Xiangtan 411105, Peoples R China
基金
中国国家自然科学基金;
关键词
CONTROLLED SELECTIVE SYNTHESIS; TRISULFUR RADICAL-ANION; S BOND FORMATION; MOLECULAR-OXYGEN; FACILE SYNTHESIS; DERIVATIVES; THIAZOLES; FUNCTIONALIZATION; OXIDATION; INDOLES;
D O I
10.1039/d0ob00074d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, iodide-catalyzed aerobic synthesis of 1,4-benzothiazines via functionalization of multiple C-H bonds with elemental sulfur is described. Beyond the well-established thiazole formation from elemental sulfur, this method provides the first access to the corresponding six-membered N,S-heterocyclic products via direct functionalization of multiple C-H bonds. Hence, 1,4-benzothiazine products were generated in satisfactory yields with a range of compatible functionalities.
引用
收藏
页码:3234 / 3238
页数:5
相关论文
共 50 条
  • [21] Palladium-Catalyzed Direct 1,4-Addition of Heteroarenes to α,β-Unsaturated Ketones via C-H Activation
    Zhang, Xuan
    Yu, Xiaoqiang
    Feng, Xiujuan
    Bao, Ming
    SYNLETT, 2012, (11) : 1605 - 1608
  • [22] Synthesis of Heteroarylogous 1H-Indole-3-carboxamidines via a Three-Component Interrupted Ugi Reaction
    La Spisa, Fabio
    Meneghetti, Fiorella
    Pozzi, Beatrice
    Tron, Gian Cesare
    SYNTHESIS-STUTTGART, 2015, 47 (04): : 489 - 496
  • [23] Iodide-Mediated or Iodide-Catalyzed Demethylation and Friedel-Crafts C-H Borylative Cyclization Leading to Thiophene-Fused 1,2-Oxaborine Derivatives
    Shigemori, Keisuke
    Watanabe, Momoka
    Kong, Julie
    Mitsudo, Koichi
    Wakamiya, Atsushi
    Mandai, Hiroki
    Suga, Seiji
    ORGANIC LETTERS, 2019, 21 (07) : 2171 - 2175
  • [24] Facile one-pot three-component strategy for the synthesis of 2-amino-4-arylthiazoles via elemental sulfur source
    Liang, Xiao-Ping
    Luo, Min
    Kang, Li
    Tang, Long-Xing
    Liang, Qing
    Liu, Yuan-Lin
    Yang, Zi
    Zhang, Chun-Tao
    Peng, Cai-Yun
    Fu, Rong-Geng
    TETRAHEDRON LETTERS, 2022, 100
  • [25] Cp*Ir(iii)-catalyzed C-H/N-H functionalization of sulfoximines for the synthesis of 1,2-benzothiazines at room temperature
    Aher, Yogesh N.
    Lade, Dhanaji M.
    Pawar, Amit B.
    CHEMICAL COMMUNICATIONS, 2018, 54 (49) : 6288 - 6291
  • [26] One-Pot Synthesis of Diverse 1,4-[60]Fullerephenols via Three-Component Umpolung Cascade Coupling of Phenols, C60, and Nucleophiles
    Zhang, Jun-Xiang
    Wu, Yuan-Ze
    Chen, Dong-Mei
    Xuan, Jun
    Li, Fei
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (35)
  • [27] Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoIII-Catalyzed Three-Component C-H Bond Addition to Internally Substituted Dienes and Carbonyls
    Sun Dongbang
    Shen, Zican
    Ellman, Jonathan A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (36) : 12590 - 12594
  • [28] Design and synthesis of novel 1,4-benzodiazepine surrogates as potential CCKA and CCKB antagonists via palladium-catalyzed three-component cascade reactions
    Dondas, H. Ali
    Belveren, Samet
    Poyraz, Samet
    Grigg, Ronald
    Kilner, Colin
    Ferrandiz-Saperas, Marcos
    Selva, Elisabet
    Sansano, Jose M.
    TETRAHEDRON, 2018, 74 (01) : 6 - 11
  • [29] Oxazolinyl-Assisted Ru(II)-Catalyzed C-H Functionalization Based on Carbene Migratory Insertion: A One-Pot Three-Component Cascade Cyclization
    Kumar, Gangam Srikanth
    Khot, Nandkishor Prakash
    Kapur, Manmohan
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (01) : 73 - 78
  • [30] Three-Component Ruthenium-Catalyzed Direct Meta-Selective C-H Activation of Arenes: A New Approach to the Alkylarylation of Alkenes
    Wang, Xin-Gang
    Li, Yuke
    Liu, Hong-Chao
    Zhang, Bo-Sheng
    Gou, Xue-Ya
    Wang, Qiang
    Ma, Jun-Wei
    Liang, Yong-Min
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (35) : 13914 - 13922