Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (6): 1422-1430.DOI: 10.6023/cjoc201801009 Previous Articles     Next Articles

Articles

微波促进下6,7-二氢-5H-环戊二烯并[4,5]噻吩并[2,3-d]嘧啶-4-胺的简便合成

纵朝阳a,b, 张立洁c, 顾梦婷a, 孙雅泉a,b,c   

  1. a 盐城师范学院药学院 盐城 224051;
    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:2018-01-05 修回日期:2018-02-26 出版日期:2018-06-25 发布日期:2018-03-08
  • 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(No.BY2016066-02)和大学生创新(No.201410324014Z)资助项目.

Facile Microwave-Assisted Synthesis of 6, 7-Dihydro-5H-cyclopenta [4, 5]thieno [2, 3-d]pyrimidin-4-amine

Zong Chaoyanga,b, Zhang Lijiec, Gu Mengtinga, Sun Yaquana,b,c   

  1. a School of Pharmacy, Yancheng Teachers University, Yancheng 224051;
    b Institute of Chemical Technology, Nanjing Tech University, Nanjing 210000;
    c Jiangsu Marine Industry Research Institute, Yancheng 224051
  • Received:2018-01-05 Revised:2018-02-26 Online:2018-06-25 Published:2018-03-08
  • Contact: 10.6023/cjoc201801009 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).

25 kinds of 6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amines were synthesized. Under microwave irradiation conditions, cyclopentanone, malononitrile and elemental sulfur reacted in ethanol to form 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (1). Compound 1 reacted with N,N-dimethylformamide dimethyl acetal to give N-(3-cyano-5,6-dihydro-4H-cyclopenta[b]-thien-2-yl)-N,N-dimethylmethanimidamide (2) under microwave irradiation conditions. Treatment of the compound 2 with aromatic amine under microwave irradiation yielded the corresponding compounds 6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine with good yields. The structures of the 25 target compounds were confirmed by melting point, NMR, IR and HRMS techniques.

Key words: 6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine, Gewald reaction, Dimroth rearrangement, microwave synthesis