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2020 , Vol. 40 >Issue 7: 2078 - 2085

DOI: https://doi.org/10.6023/cjoc202002007

研究论文

可见光促进N-苯丙炔胺与磺酰肼的环化:在无碱和催化剂下快速合成3-磺酰基喹啉衍生物

  • 彭美 ,
  • 郑扬帆 ,
  • 黄浩 ,
  • 叶佳 ,
  • 邓兴国 ,
  • 何纯莲
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  • a 湖南师范大学药学院 小分子靶向药物研究与创制湖南省重点实验室 长沙 410081;
    b 宜春学院化学与生物工程学院 江西宜春 336000;
    c 湖南食品药品职业学院 长沙 410081

收稿日期: 2020-02-06

  修回日期: 2020-03-25

  网络出版日期: 2020-04-13

基金资助

国家自然科学基金（Nos.21176063，81803720）、湖南省自然科学基金（（Nos.18JJ5018，2019JJ50383）、小分子靶向药物研究与创制湖南省重点实验室开放基金（No.2019CG06）资助项目.

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Visible-Light-Induced Cycloaddition Involving N-Propargylanilines with Arylsulfonylhydrazides: Rapid Access to 3-Sulfonated Quinoline Derivatives without Base and Catalyst

  • Peng Mei ,
  • Zheng Yangfan ,
  • Huang Hao ,
  • Ye Jia ,
  • Deng Xingguo ,
  • He Chunlian
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  • a Key Laboratory of Study and Discovery of Small Targeted Molecules of Hunan Province, School of Medicine, Hunan Normal University, Changsha 410081;
    b School of Chemistry and Bioengineering, Yichun University, Yichun, Jiangxi 336000;
    b Hunan Food and Drug Vocational College, Changsha 410081

Received date: 2020-02-06

  Revised date: 2020-03-25

  Online published: 2020-04-13

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21176063, 81803720), the Hunan Provincial Natural Science Foundation (Nos. 18JJ5018, 2019JJ50383), and the Department of Science and Technology Foundation of Changsha City (Nos. kq1706047, kq1801038), and the Key Laboratory of Study and Discovery of Small Targeted Molecules of Hunan Province (No. 2019CG06).

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摘要

利用可见光照射和过氧化叔丁醇作氧化剂的条件，发展了N-芳基苯丙炔胺和磺酰肼类化合物的自由基环化-氧化芳构化反应.该反应提供了一种合成3-磺酰基喹啉衍生物的有效方法，显示出较好的官能团适用性、底物普适性以及很好的化学与区位选择性.

关键词： 可见光; 磺酰肼; 3-磺酰基喹啉衍生物; 区位选择性

本文引用格式

彭美 , 郑扬帆 , 黄浩 , 叶佳 , 邓兴国 , 何纯莲 . 可见光促进N-苯丙炔胺与磺酰肼的环化:在无碱和催化剂下快速合成3-磺酰基喹啉衍生物[J]. 有机化学, 2020 , 40(7) : 2078 -2085 . DOI: 10.6023/cjoc202002007

Abstract

A visible-light-induced oxidative cyclization of N-propargylanilines with arylsulfonylhydrazides was developed using tert-butyl hydroperoxide as oxidant. This transformation offers a straightforward route to 3-sulfonated quinoline derivatives with good functional group tolerance, good to excellent yields and high regio-selectivity.

Key words： visible-light; arylsulfonylhydrazides; 3-sulfonated quinoline derivatives; regio-selectivity

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