有机化学 ›› 2015, Vol. 35 ›› Issue (10): 2059-2066.DOI: 10.6023/cjoc201505009 上一篇    下一篇

综述与进展

磺酰叠氮和炔参与的多组分反应研究进展

张文生a, 许文静a, 匡春香b   

  1. a 焦作师范高等专科学校理工学院 焦作 454001;
    b 同济大学化学系 上海 200092
  • 收稿日期:2015-05-06 修回日期:2015-06-02 发布日期:2015-06-16
  • 通讯作者: 张文生 E-mail:tongjizws@163.com
  • 基金资助:

    国家自然科学基金(No. 21272174)、河南省自然科学基金(No. 142300410338)、河南省教育厅自然科学重点研究计划(No. 14B150056)和焦作市科学技术局科技计划(No. 2014400038)资助项目.

Research Progress on Multicomponent Reactions of Sulfonyl Azides and Terminal Alkynes

Zhang Wenshenga, Xu Wenjinga, Kuang Chunxiangb   

  1. a School of Technology, Jiaozuo Teachers College, Jiaozuo 454001;
    b Department of Chemistry, Tongji University, Shanghai 200092
  • Received:2015-05-06 Revised:2015-06-02 Published:2015-06-16
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272174), the Foundation of He'nan Scientific and Technological Committee (No. 142300410338), the Science and Technology Research Key Program of Henan Educational Committee (No. 14B150056) and the Foundation of Jiaozuo Scientific and Technological Bureau (No. 2014400038).

磺酰叠氮和炔参与的铜催化多组分反应成为近年来有机化学研究的热点. 磺酰叠氮和炔在铜催化下生成的N-磺酰基烯酮亚胺中间体, 可以被胺、醇和水等各类亲核试剂捕捉, 也可以和各种类型的烯烃发生[2+2]、[3+2]和[4+2]等环加成反应. N-磺酰基烯酮亚胺中间体受到来自双官能团底物的分子内基团进攻以及随后发生的(环)重排和σ键迁移, 更是成为构建结构丰富的具有生理和药物活性(杂)环类化合物的重要手段. 主要对该领域近年来的最新研究成果进行了综述.

关键词: 磺酰叠氮, 炔, 烯酮亚胺, 多组分反应, 铜催化

In recent years, the copper-catalyzed multicomponent reactions involving sulfonyl azides and terminal alkynes have received much attention in organic chemistry. N-Sulfonyl ketenimine intermediates, generated in situ from the copper(I)-catalyzed cycloaddition of sulfonyl azides and terminal alkynes, could be trapped by various nucleophiles such as amines, alcohols and H2O, etc. In addition, the ketenimine intermediates could also react with a wide range of olefins though [2+2], [3+2] and [4+2] cycloadditions. Moreover, attack of the ketenimine by intramolecular nucleophilic functional group and the following rearrangement or σ-shift course have become a powerful tool for the construction of diverse biologically and pharmacologically active heterocyclic compounds. In this paper, the research achievements recently in the important area are described.

Key words: sulfonyl azide, alkyne, ketenimine, multicomponent reaction, copper-catalyzed