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The complete synthesis of favipiravir from 2-aminopyrazine

文献类型：期刊论文

作者Guo, Qi1,3; Xu, Mingshuo1,3; Guo, Shuang1,3; Zhu, Fuqiang2; Xie, Yuanchao3; Shen, Jingshan1,3
刊名CHEMICAL PAPERS
出版日期2019-05-01
卷号73期号:5页码:1043-1051
关键词Favipiravir 2-Aminopyrazine Fluorination Sandmeyer reaction
ISSN号2585-7290
DOI10.1007/s11696-018-0654-9
通讯作者Xie, Yuanchao(xieyuanchao@simm.ac.cn)
英文摘要Favipiravir was first synthesized from an inexpensive and commercially available starting material, 2-aminopyrazine. The preferred route embedded within Scheme4 consisted of seven steps, and was highlighted by the novel and efficient synthesis of 3,6-dichloropyrazine-2-carbonitrile 8. This intermediate was prepared in four successive steps which were regioselective chlorination of the pyrazine ring, bromination, Pd-catalyzed cyanation, and Sandmeyer diazotization/chlorination. This protocol eliminated the hazardous POCl3 of previous synthetic methods and offered a better yield (48%) which was 1.3-fold higher than a recently published procedure. From intermediate 8, the subsequent nucleophilic fluorination, nitrile hydration and hydroxyl substitution efficiently afforded the target product. Another synthetic approach with the same starting material was also investigated to bypass the allergy-causing dichloro intermediate 8. However, the key step of monofluorination at the pyrazine C6 position of intermediate 19 or 22 was not achieved.
WOS关键词T-705 FAVIPIRAVIR ; INHIBITORS
资助项目National Science Foundation for Young Scientists of China[21502209]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000463985400002
出版者SPRINGER INTERNATIONAL PUBLISHING AG
源URL[http://119.78.100.183/handle/2S10ELR8/289972]  
专题中国科学院上海药物研究所
通讯作者Xie, Yuanchao
作者单位1.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China
2.Topharman Shanghai Co Ltd, 388 Jialilue Rd,Zhangjiang Hitech Pk, Shanghai 201203, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China
推荐引用方式
GB/T 7714		 Guo, Qi,Xu, Mingshuo,Guo, Shuang,et al. The complete synthesis of favipiravir from 2-aminopyrazine[J]. CHEMICAL PAPERS,2019,73(5):1043-1051.
APA Guo, Qi,Xu, Mingshuo,Guo, Shuang,Zhu, Fuqiang,Xie, Yuanchao,&Shen, Jingshan.(2019).The complete synthesis of favipiravir from 2-aminopyrazine.CHEMICAL PAPERS,73(5),1043-1051.
MLA Guo, Qi,et al."The complete synthesis of favipiravir from 2-aminopyrazine".CHEMICAL PAPERS 73.5(2019):1043-1051.

入库方式： OAI收割

来源：上海药物研究所

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