Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (5): 1165-1171.DOI: 10.6023/cjoc201711028 Previous Articles     Next Articles

Articles

微波促进的Dimroth重排反应合成吡啶并[2,3-d]嘧啶-4-胺衍生物

纵朝阳a,b, 顾惠雯b, 张立洁c, 金煜东a, 孙雅泉a,b,c   

  1. a 盐城师范学院药学院 盐城 224007;
    b 南京工业大学化工学院 南京 210000;
    c 江苏海洋产业研究院 盐城 224051
  • 收稿日期:2017-11-19 修回日期:2018-01-03 出版日期:2018-05-25 发布日期:2018-01-26
  • 通讯作者: 孙雅泉,E-mail:sunyaquan@hotmail.com E-mail:sunyaquan@hotmail.com
  • 基金资助:

    江苏省前瞻科研项目(No.BY2016066-02)和大学生创新(No.201410324014Z)资助项目.

Microwave-Accelerated Dimroth Rearrangement for the Synthesis of Pyrido [2, 3-d]pyrimidin-4-amine Derivatives

Zong Chaoyanga,b, Gu Huiwenb, Zhang Lijiec, Jin Yudonga, Sun Yaquana,b,c   

  1. a School of Pharmacy, Yancheng Teachers University, Yancheng 224007;
    b Institute of Chemical Technology, Nanjing Tech University, Nanjing 210000;
    c Jiangsu Marine Industry Research Institute, Yancheng 224051
  • Received:2017-11-19 Revised:2018-01-03 Online:2018-05-25 Published:2018-01-26
  • Contact: 10.6023/cjoc201711028 E-mail:sunyaquan@hotmail.com
  • Supported by:

    Project supported by the Jiangsu Prospective Joint Research Project (No. BY2016066-02) and the College Students Innovation Project (No. 201410324014Z).

In this paper, a novel synthetic method for N-(3, 5-dichlorophenyl)pyrido [2, 3-d]pyrimidin-4-amine was reported, which began from 2-aminonicotinonitrile, following condensation, cyclization and then Dimroth rearrangement reaction under microwave irradiation conditions. The over yield was 90%. Employing the same synthetic method, 20 pyrido [2, 3-d]pyrimidin- 4-amine derivatives were synthesized. We also compared microwave irradiation and oil bath heating for synthetizing the target products. The results showed that the method under microwave irradiation for the preparation of pyrido [2, 3-d]pyrimidin- 4-amine was time-saving and high yield. It is expected to become an efficient, gentle and environmentally friendly synthetic method of pyrido [2, 3-d]pyrimidin-4-amine.

Key words: pyrido[2, 3-d]pyrimidin-4-amine, Dimroth rearrangement, organic synthesis, microwave irradiation