AcOH-mediated aerobic oxidative synthesis of 2-thioalkylbenzothiazoles via a three-component reaction

被引：2
|
作者：
Li, Xiaowei [1 ,3 ,4 ]
Li, Yuxiu [2 ]
Liu, Ruihua [2 ]
Wang, Zemin [2 ]
Li, Xiangqian [2 ]
Shi, Dayong [2 ,3 ,4 ]
机构：
[1] Chinese Acad Sci, Inst Oceanol, Key Lab Expt Marine Biol, 7 Nanhai Rd, Qingdao 266071, Shandong, Peoples R China
[2] Shandong Univ, State Key Lab Microbial Technol, 72 Binhai Rd, Qingdao 266237, Peoples R China
[3] Qingdao Natl Lab Marine Sci & Technol, Lab Marine Drugs & Bioprod, Qingdao 266000, Peoples R China
[4] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
TETRAHEDRON LETTERS | 2020年 / 61卷 / 26期
基金：
中国国家自然科学基金; 中国博士后科学基金;
关键词：
2-Thioalkylbenzothiazoles; Metal-free; Aerobic oxidation; Multicomponent reaction; ONE-POT SYNTHESIS; HIGHLY EFFICIENT; 2-SUBSTITUTED BENZOTHIAZOLES; CATALYZED SYNTHESIS; PROMOTED SYNTHESIS; BENZIMIDAZOLES; DERIVATIVES; BENZOXAZOLES; ANTITUMOR; DESIGN;
D O I：
10.1016/j.tetlet.2020.152054
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An AcOH-mediated three-component reaction of 2-aminothiophenols, alpha,beta-unsaturated aldehydes, and thiophenols to prepare the high value-added 2-thioalkylbenzothiazoles was developed. The reaction was conducted under metal-free conditions, where oxygen served as the terminal oxidant. In addition, this strategy is tolerant of kinds of functional groups, providing efficient access to a variety of functionalized benzothiazole derivatives in moderate to good yields. What's more, this reaction has complete regioslectivity and provides a powerful method for building complex molecules. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数：5
相关论文
共 50 条
  • [1] AcOH catalyzed three-component synthesis of spirooxindole derivatives
    Yang, Peng Hui
    Qu, Cheng Tun
    Wang, Wen Zhen
    RESEARCH ON CHEMICAL INTERMEDIATES, 2013, 39 (02) : 463 - 468
  • [2] AcOH catalyzed three-component synthesis of spirooxindole derivatives
    Peng Hui Yang
    Cheng Tun Qu
    Wen Zhen Wang
    Research on Chemical Intermediates, 2013, 39 : 463 - 468
  • [3] Three-Component Synthesis of Tetrahydroisoquinolines via SNVin Reaction
    Dyachenko, I. V.
    Dyachenko, V. D.
    Dorovatovskii, P. V.
    Khrustalev, V. N.
    Nenajdenko, V. G.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 60 (09) : 1619 - 1629
  • [4] Access to Phenothiazine Derivatives via Iodide-Mediated Oxidative Three-Component Annulation Reaction
    Chen, Qinghua
    Xie, Rong
    Jia, Huanhuan
    Sun, Jialu
    Lu, Guangpeng
    Jiang, Huanfeng
    Zhang, Min
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (08): : 5629 - 5637
  • [5] Passerini Three-Component Reaction of Alcohols under Catalytic Aerobic Oxidative Conditions
    Brioche, Julien
    Masson, Geraldine
    Zhu, Jieping
    ORGANIC LETTERS, 2010, 12 (07) : 1432 - 1435
  • [6] Convergent Synthesis of Dendrimers via the Passerini Three-Component Reaction
    Jee, Jo-Ann
    Spagnuolo, Lauren A.
    Rudick, Jonathan G.
    ORGANIC LETTERS, 2012, 14 (13) : 3292 - 3295
  • [7] Synthesis of Spiro Pyrrolobenzothiazole Derivatives via a Three-Component Reaction
    Nassiri, M.
    Milani, F. J.
    Hassankhani, A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (04) : 1162 - 1166
  • [8] Synthesis of Unsaturated α-Acyloxybenzothiazoleamides via the Passerini Three-Component Reaction
    Sheikholeslami-Farahani, Fatemeh
    Shahvelayati, Ashraf S.
    COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2013, 16 (09) : 726 - 730
  • [9] Convergent synthesis of dendrimers via the Passerini three-component reaction
    Jee, Jo-Ann
    Rudick, Jonathan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [10] A base-mediated three-component coupling reaction for the synthesis of phosphorohydrazones
    Wen, Jun
    Dong, Liang
    Yang, Liang
    Jiang, Tao
    Hu, Sheng
    Yang, Tong-Zai
    Wang, Xiao-Lin
    TETRAHEDRON, 2013, 69 (47) : 10068 - 10072
12345