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Microwave- and Ionic Liquids-Based Sustainable Preparation of 2-Acylbenzothiazoles
  • +8
  • Wang Shoushun,
  • Liu Mengjie,
  • Yue Yiyuan,
  • Hu Xiude,
  • Zhang Yalin,
  • Li Zhen,
  • Shen Guodong,
  • Dong Ruiguo,
  • Shi Lilong,
  • Bing Yu,
  • Xianqiang Huang
Wang Shoushun
Liao Cheng University
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Liu Mengjie
Liao Cheng University
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Yue Yiyuan
Liao Cheng University
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Hu Xiude
Ningxia University
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Zhang Yalin
Liao Cheng University
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Li Zhen
Liao Cheng University
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Shen Guodong
Liao Cheng University
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Dong Ruiguo
National Rubber Additive Engineering Technology Center
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Shi Lilong
National Rubber Additive Engineering Technology Center
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Bing Yu
Zhengzhou University
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Xianqiang Huang
Liao Cheng University

Corresponding Author:hxq@lcu.edu.cn

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Abstract

Microwave irradiation (MW) and ionic liquids (ILs) are two of the most promising relatively greener synthetic approaches for preparing the value-added chemicals. The breakthrough of their combination in the generation of 2-acylbenzothiazoles is unprecedented and de-sirable. Herein, a series of 2-acylbenzothiazole derivatives were synthesized for the first time from the commercially available α-bromoacetophenones and disulfanediyldianilines under the cooperation of ionic liquids and microwave irradiation, metal- and ex-tra-additives-free conditions. Significantly, the dialkylated [PMIM]I (PMIM = propyl methyl imidazolium) ILs is utilized as the optimal al-ternatives for the cyclization to furnish the 2-acylbenzothiazole and at least reused four times without losing of the reaction activities. Furthermore, thus-obtained products have been further converted to the desired products via Suzuki and Sonogashira reaction. A plausi-ble mechanism involved the successive ILs-induced enolation, radical addition, intramolecular cyclization and MW-induced oxidative dehydrogenation was also proposed. The simplicity and sustainability of MW-assisted ILs-mediated reaction conditions for accessing functionalized benzothiazoles is remarkable and could lead to many synthetic innovations in biologically active molecules.