Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1563-1571.DOI: 10.6023/cjoc202102018 Previous Articles     Next Articles



吴亚男a,b,*(), 杜建宇b, 郝文娟b, 姜波b,*()   

  1. 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 发布日期:2021-02-26
  • 通讯作者: 吴亚男, 姜波
  • 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

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

Yanan Wua,b,*(), Jianyu Dub, Wenjuan Haob, Bo Jiangb,*()   

  1. a School of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019
    b School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
  • Received:2021-02-04 Revised:2021-02-10 Published:2021-02-26
  • Contact: Yanan Wu, Bo Jiang
  • About author:
    * Corresponding author. E-mail: ;
  • Supported by:
    National Natural Science Foundation of China(21971090); Top-notch Academic Programs Project of Jiangsu Higher Education Institutions

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