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Paper | Regular issue | Vol 92, No. 5, 2016, pp.866-885
Published online, 30th March, 2016
DOI: 10.3987/COM-16-13427
Efficient Constructions of the Four Different Thienopyrimidinone Skeletons via Various Cyclocondensation of o-Aminothienonitrile with Carbonyl Compounds

Junjuan Yang, Daxin Shi, Kai Zhang, Zhangtao Zhao, Fadong Qiu, Yujiao Bi, Qi Zhang, and Jiarong Li*

*Department of Chemical Engineering, Beijing Institute of Technology, 5 South Zhongguancun Street, Haidian District, Beijing Postcode: 100081, China

Abstract

A series of new thienopyrimidinone derivatives were synthesized via a novel, straightforward and efficient tandem cyclocondensation of o-aminothienonitrile 1 and carbonyl compounds 2 in different conditions. The synthesized four thienopyrimidinone skeletons were thieno[2,3-d]pyrimidinone 3, tert-hydroxythieno[2,3-d]pyrimidinone 4, symmetrical tetracycle thienothiophenepyrimidone 5 and thienopyrimidine 6 respectively. Their plausible mechanisms were proposed. The properties of compound 5 were investigated.