有机化学 ›› 2022, Vol. 42 ›› Issue (8): 2527-2534.DOI: 10.6023/cjoc202203055 上一篇    下一篇

研究论文

N-(2-丙炔基)苯胺和磺酰氯直接合成3-砜基喹啉

王苛莉a, 黄静a, 刘伟b, 伍智林a, 于贤勇b, 蒋俊a,*(), 何卫民a,*()   

  1. a 南华大学化学化工学院 湖南衡阳 411201
    b 湖南科技大学理论有机化学与功能分子教育部重点实验室 湖南湘潭 411201
  • 收稿日期:2022-03-28 修回日期:2022-04-26 发布日期:2022-05-06
  • 通讯作者: 蒋俊, 何卫民
  • 基金资助:
    湖南省教育厅科学研究项目(19C0783); 湖南省科技创新计划项目(2021RC5028)

Direct Synthesis of 3-Sulfonylquinolines from N-Propargylanilines with Sulfonyl Chlorides

Keli Wanga, Jing Huanga, Wei Liub, Zhilin Wua, Xianyong Yub, Jun Jianga(), Weimin Hea()   

  1. a School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001
    b Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan University of Science and Technology, Xiangtan, Hunan 411201
  • Received:2022-03-28 Revised:2022-04-26 Published:2022-05-06
  • Contact: Jun Jiang, Weimin He
  • Supported by:
    Scientific Research Fund of Hunan Provincial Education Department(19C0783); Science and Technology Innovation Program of Hunan Province(2021RC5028)

3-砜基喹啉广泛存在于多种生物活性分子和合成药物中. 报道了一种温和条件下, 以N-炔丙基苯胺和磺酰氯为原料, 通过一锅法连续肼化/砜化/环化反应高效构建3-砜基喹啉类化合物的方法. 该方法不仅可以进行克级合成, 还可用于药物分子砜基衍生物的合成.

关键词: 3-砜基喹啉, N-炔丙基苯胺, 磺酰氯, 一锅法, 环化反应

3-Sulfonylquinolines broadly exist in plenty of bioactive molecules and synthetic pharmaceuticals. Herein, an efficient and facile method for direct synthesizing various 3-sulfonylquinolines through one-pot sequential hydrazination/sulfonylation/cyclization reaction from N-propargylanilines and sulfonyl chlorides under mild reaction conditions is reported. This procedure not only can be performed on a gram scale but also be applicable to prepare marketed pharmaceutical derivative.

Key words: 3-sulfonylquinolines, N-propargylanilines, sulfonyl chlorides, one pot, cyclization reaction