Citation: Zong Chaoyang, Zhang Lijie, Gu Mengting, Sun Yaquan. Facile Microwave-Assisted Synthesis of 6, 7-Dihydro-5H-cyclopenta [4, 5]thieno [2, 3-d]pyrimidin-4-amine[J]. Chinese Journal of Organic Chemistry, ;2018, 38(6): 1422-1430. doi: 10.6023/cjoc201801009 shu

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

Zong Chaoyang ^a,b ,
Zhang Lijie ^c ,
Gu Mengting ^a ,
Sun Yaquan ^a,b,c,,

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

Corresponding author: Sun Yaquan, sunyaquan@hotmail.com
Received Date: 5 January 2018
Revised Date: 26 February 2018
Available Online: 8 June 2018
Fund Project: the Jiangsu Prospective Joint Research Project BY2016066-02Project supported by the Jiangsu Prospective Joint Research Project (No. BY2016066-02) and the College Students Innovation Project (No. 201410324014Z)the College Students Innovation Project 201410324014Z

Figures(3)

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