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

doi:10.6023/cjoc201801009

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

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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

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 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

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).

1. Facile Microwave-Assisted Synthesis of 6, 7-Dihydro-5H-cyclopenta [4, 5]thieno [2, 3-d]pyrimidin-4-amine.PDF(2510KB)

Abstract

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

Cite this article

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]. Chin. J. Org. Chem., 2018, 38(6): 1422-1430.

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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

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

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