An Alternative Approach to Synthesize Sildenafil via Improved Copper-Catalyzed Cyclization
文献类型：期刊论文
| 作者 | Odilov, Abdullajon3,4; Gong, Xudong1; Qin, Hongjian2,3; Bonku, Emmanuel Mintah3,4; Zhu, Fuqiang1; Yang, Feipu4; Shen, Jingshan3,4
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| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
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| 出版日期 | 2024-05-06 |
| 卷号 | 89期号:10页码:7303-7311 |
| ISSN号 | 0022-3263 |
| DOI | 10.1021/acs.joc.4c00393 |
| 通讯作者 | Shen, Jingshan(shenjingshan@simm.ac.cn) |
| 英文摘要 | A facile synthetic pathway for sildenafil has been developed. This approach is characterized by a ligand-free Ullmann-type copper-catalyzed coupling reaction to construct sildenafil and its derivative, pyrrazolo[4,3-d]pyrimidin-7-one ring, with yields of 79% and 82%, respectively, in a convergent fashion by connecting key building blocks halo-pyrazole moiety 16c with 2-ethoxybenzamidine and 2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]benzamidine in a one-pot reaction. Thus, this approach circumvents the need to use nitric/sulfuric acid for nitration, a costly Pd-catalyst for reduction, and coupling agents encountered in the reported processes. |
| WOS关键词 | QUINAZOLINONES ; EFFICIENT ; NITRATION ; BROMIDES ; CU |
| 资助项目 | Chinese Academy of Sciences[XDA12050411] ; Special Foundation of Chinese Academy of Sciences for strategic pilot technology[18431907100] ; Science and Technology Commission of Shanghai Municipality ; Alliance of International Science Organizations (ANSO) ; ANSO Scholarship for Young Talents |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:001225119500001 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/311273]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Shen, Jingshan |
| 作者单位 | 1.Topharman Shanghai Co Ltd, Shanghai 201203, Peoples R China 2.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Reg, Urumqi 830011, Xinjiang, Peoples R China 3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 4.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Odilov, Abdullajon,Gong, Xudong,Qin, Hongjian,et al. An Alternative Approach to Synthesize Sildenafil via Improved Copper-Catalyzed Cyclization[J]. JOURNAL OF ORGANIC CHEMISTRY,2024,89(10):7303-7311. |
| APA | Odilov, Abdullajon.,Gong, Xudong.,Qin, Hongjian.,Bonku, Emmanuel Mintah.,Zhu, Fuqiang.,...&Shen, Jingshan.(2024).An Alternative Approach to Synthesize Sildenafil via Improved Copper-Catalyzed Cyclization.JOURNAL OF ORGANIC CHEMISTRY,89(10),7303-7311. |
| MLA | Odilov, Abdullajon,et al."An Alternative Approach to Synthesize Sildenafil via Improved Copper-Catalyzed Cyclization".JOURNAL OF ORGANIC CHEMISTRY 89.10(2024):7303-7311. |
入库方式： OAI收割
来源：上海药物研究所
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