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2021 , Vol. 41 >Issue 4: 1563 - 1571

DOI: https://doi.org/10.6023/cjoc202102018

研究论文

利用微波辅助[3+3]环化反应合成稠合吡啶衍生物

  • 吴亚男 ,
  • 杜建宇 ,
  • 郝文娟 ,
  • 姜波
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  • a 南通大学化学化工学院 江苏南通 226019
    b 江苏师范大学化学与材料科学学院 江苏徐州 221116

收稿日期: 2021-02-04

  修回日期: 2021-02-10

  网络出版日期: 2021-02-26

基金资助

国家自然科学基金(21971090); 江苏省品牌专业基金资助项目

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Synthesis of Fused Pyridines via Microwave-Assisted [3+3] Cyclization

  • Yanan Wu ,
  • Jianyu Du ,
  • Wenjuan Hao ,
  • Bo Jiang
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  • a School of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019
    b School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
* Corresponding author. E-mail: ;
E-mail:

Received date: 2021-02-04

  Revised date: 2021-02-10

  Online published: 2021-02-26

Supported by

National Natural Science Foundation of China(21971090); Top-notch Academic Programs Project of Jiangsu Higher Education Institutions

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摘要

报道了一类新型的微波辅助对甲基苯磺酸促进的[3+3]环化反应. 利用烯胺酮或烯胺内酯可作为1,3-双亲核试剂及炔丙醇可作为1,3-双亲电试剂的特性, 使其在微波辐射及对甲苯磺酸促进条件下于冰醋酸中在70 ℃反应, 实现了[3+3]环化反应, 分别区域选择性地合成了2,2-二芳基取代四氢喹啉-5(1H)-酮衍生物和2,2-二芳基取代二氢呋喃并[3,4-b]吡啶-5-酮衍生物, 产率良好. 该反应利用微波合成技术促使反应, 在短时间内完成(30 min), 唯一副产物为水. 此外, 该方法具有原料简单易得、操作简单及底物普适性广等优点, 从而为具有潜在应用价值的稠合吡啶骨架的构建提供了一种绿色、经济且高效的合成策略, 符合绿色化学理念.

关键词： 微波合成; [3+3]环化; 喹啉-5(1H)-酮衍生物; 呋喃并[3,4-b]吡啶-5-酮衍生物; 绿色化学

本文引用格式

吴亚男 , 杜建宇 , 郝文娟 , 姜波 . 利用微波辅助[3+3]环化反应合成稠合吡啶衍生物[J]. 有机化学, 2021 , 41(4) : 1563 -1571 . DOI: 10.6023/cjoc202102018

Abstract

A new microwave-assisted p-TsOH-promoted [3+3] cyclization was developed. By using the characteristics of enaminones or enamino lactones as 1,3-dinucleaphilic reagents and propargyl alcohols as 1,3-electrophilic reagents, p-TsOH- promoted [3+3] cyclization of these substrates at 70 ℃ was carried out in acetic acid under microwave irradiation, regioselectively affording 2,2-diaryl-substituted tetrahydroquinoline-5(1H)-ones and 2,2-diaryl-substituted dihydrofuro[3,4-b]pyridin- 5-ones in good yields. The reaction can be completed within a short period (30 min) by microwave synthetic technology, in which water was the sole by-product. This method features simple and available starting materials, simple operation and wide substrate scope, and provides a green, economic, and efficient synthetic strategy for the construction of fused pyridine skeleton with potential application, which is consistent with the concept of green chemistry.

Key words： microwave synthesis; [3+3] cyclization; quinoline-5(1H)-one; furo[3,4-b]pyridin-5-one; green chemistry

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