高等学校化学学报

高等学校化学学报

• 研究论文 • 上一篇    下一篇

钯催化合成噻吩并[2,3-b]噻喃-4-酮类化合物

任传清，季晓晖，张  强，曹小燕，季建伟，刘  波   

  1. 陕西理工大学化学与环境科学学院，陕西省催化基础与应用重点实验室，汉中 723000
  • 收稿日期:2024-01-19 修回日期:2024-03-05 出版日期:2024-03-06 发布日期:2024-03-06
  • 通讯作者: 任传清 E-mail:rcqing2008@126.com
  • 基金资助:
    国家自然科学基金项目(No.22101165)和陕西省教育厅重点实验室项目(No. 23JS002)资助.

Synthesis of Thieno[2,3-b]thiopyran-4-one Derivatives by Palladium Catalysts

REN Chuanqing, JI Xiaohui, ZHANG Qiang, CAO Xiaoyan, JI Jianwei, LIU Bo   

  1. Shaanxi Key laboratory of Catalysis, School of Chemical & Environmental Science, Shaanxi University of Technology, Hanzhong 723000, China
  • Received:2024-01-19 Revised:2024-03-05 Online:2024-03-06 Published:2024-03-06
  • Contact: REN Chuanqing E-mail:rcqing2008@126.com
  • Supported by:
    Supported by the National Natural Science Foundation of China(No. 22101165) and the Project of the Key Laboratory of Education Department of Shaanxi Province (No. 23JS002).

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摘要： 噻吩并[2,3-b]噻喃骨架化合物是一类重要的有机分子并广泛存在于天然产物中，也是一类重要的的生物活性分子，本论文以1,6-二取代基-4-(1,3-二硫戊环-2-亚基)-己烯-5-炔-3-酮类化合物为原料，通过钯催化环合反应合成了一系列噻吩并[2,3-b]噻喃-4-酮类化合物。实验探索表明，最佳实验条件如下：以30 %倍当量Pd(OAc)2作为催化剂，1.0倍当量的底物和1.2倍当量K2CO3，在DMF溶剂中，于100℃下反应8小时，以较高的收率得到噻吩并[2,3-b]噻喃-4-酮类化合物，产物结构经1H NMR、13C NMR以及HR-MS(ESI)分析确证，并对该反应合成机理进行了探讨. 该合成方法条件温和、操作安全、收率高.

关键词: 醋酸钯, 催化, 噻吩并[2,3-b]噻喃, 二硫缩烯酮

Abstract: Thieno[2,3-b]thiopyrans are important core structures found in a variety of natural products and other biologically important molecules with a wide range of biological activities. In this paper, a series of Thieno[2,3-b]thiopyrans were successfully constructed from 1,6-disubstituted group-4-(1,3-dithiolan-2-ylidene)-1- en -5-yn-3-one via palladium-catalyzed cycloaddition reactions. Optimization experiments showed that the best experimental conditions were as follows: using Pd(OAc)2 (30 mol% equiv) as catalyst，the substrate (1.0 equiv) and K2CO3 (1.2 equiv) reacted at 100℃ for 8 h in DMF. The composition and structure has been characterized by 1H NMR, 13C NMR and HR-MS(ESI). The mechanism for the reaction was proposed in this paper. The menthod had the advantages of mild conditions, safe operation and higher yields.

Key words: Palladium acetate, Catalyze, Thiophene[2,3-b]thiapyran, Ketene dithioacetals

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