有机化学 ›› 2018, Vol. 38 ›› Issue (6): 1422-1430.DOI: 10.6023/cjoc201801009 上一篇    下一篇

研究论文

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 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 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).

微波辐射条件下,以乙醇作溶剂,环戊酮、丙二腈与单质硫反应得到2-氨基-5,6-二氢-4H-环戊二烯[b]噻吩-3-腈(1),1NN-二甲基甲酰胺二甲基缩醛在微波辐射条件下反应得到N-(3-氰基-5,6-二氢-4H-环戊二烯[b]-硫基-2-基)-NN-二甲基亚甲基酰胺(2),进一步在微波辐射条件下由N-(3-氰基-5,6-二氢-4H-环戊二烯[b]-硫基-2-基)-NN-二甲基亚甲基酰胺(2)与取代芳香胺反应制得目标化合物.合成的25个目标化合物通过熔点测定和核磁共振氢谱分析、红外光谱、高分辨质谱对其结构进行确证.

关键词: 6,7-二氢-5H-环戊二烯并[4,5]噻吩并[2,3-d]嘧啶-4-胺, Gewald反应, Dimroth重排, 微波合成

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