有机化学    下一篇

综述与进展

硫原子作为自由基受体在含硫杂环合成中的研究进展

杨文超a, 张明明a, 陈旺a, 杨小虎b, 冯建国a   

  1. a 扬州大学园艺与植物保护学院 江苏扬州 225009;
    b 浙江医院药剂科 浙江杭州 310013
  • 收稿日期:2020-05-16 修回日期:2020-06-12 出版日期:2030-01-01 发布日期:2020-07-23
  • 通讯作者: 杨文超, 冯建国 E-mail:wccyang@126.com; jgfeng@yzu.edu.cn
  • 基金资助:
    江苏省高校自然科学基金(No.19KJB150020)、江苏省青年基金(Nos.BK20170489,BK20190900)、江苏省农业自主创新基金(CX (19)3112)资助项目.

Sulfur Atom as Radical Acceptors in the Synthesis of Sulfur-Containing Heterocycles

Yang Wenchaoa, Zhang Mingminga, Chen Wanga, Yang Xiaohub, Feng Jianguoa   

  1. a School of Horticulture and Plant Protection, Yangzhou University, Yangzhou, 225009;
    b Department of Pharmacy, Zhejiang Hospital, Hangzhou, 310013
  • Received:2020-05-16 Revised:2020-06-12 Online:2030-01-01 Published:2020-07-23
  • Supported by:
    Project supported by the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (No. 19KJB150020), Natural Science Foundation for Young Scholars of Jiangsu Province (Nos. BK20170489, BK20190900) and the Agricultural Science and Technology Innovation Fund (CX(19)3112).

含硫杂环化合物如噻唑, 噻吩, 硫代黄酮等, 广泛存在于天然产物及生物活性分子中, 因其具有多样的生物活性, 在药物化学、有机化学和功能性材料领域中的研究潜力越来越突出. 有效的含硫杂环合成策略已成为广泛研究的主题. 不饱和烃的自由基串联反应构筑杂环衍生物一直是有机合成化学的一个重要研究分支, 近年来的研究成果也彰显了其巨大的潜力. 研究者发现硫原子可以作为自由基的受体构建一个C-S键, 自此合成化学家通过该策略建立了一系列自由基串联反应, 其中基于茴香硫醚参与的不饱和烃自由基串联反应已逐渐发展成为一种重要的含硫杂环合成工具. 本文综述了该领域的研究进展, 根据茴香硫醚的成环类型, 对近年来硫醚中硫原子作为自由基受体参与杂环合成的反应进行简要总结, 并对反应设计、机理研究、研究展望等给予评述.

关键词: 茴香硫醚, 杂环, 自由基串联反应, 双官能化

Sulfur-containing heterocyclic compounds such as thiazole, thiophene, thiopyrone, widely exist in numerous natural products and biologically active molecules. Developing of effective strategies for the formation of sulfur-containing heterocycles has become a popular research hotspot. Meanwhile, the free-radical cascade reaction of unsaturated bonds in the synthesis of heterocycle has always been an important branch of synthetic chemistry, and the achieved progresses in recent years have also demonstrated its huge potential. Researchers found that sulfur atom could act as radical acceptors to build a C-S bond, and synthetic chemists have established a series of free radical reactions through this strategy. Among them, the radical cascade reactions of anisole derivatives has gradually developed into an important synthetic tool toward sulfur-containing heterocycles. In this review, we summarize recent advances in the field of radical-initiated reactions of anisoles for the construction of sulfur-containing heterocycles, in which sulfur atoms play as radical acceptors. In addition, the reaction design, mechanism and applicability of sulfur-containing heterocyclic compounds via radical cyclization towards the synthesis of complex molecules will also be covered.

Key words: anisole, heterocycles, radical cascade reactions, difunctionalization