Facile Synthesis of Substituted 4-Alkoxy-2-oxazolines and Exploration of the Reaction Mechanism
文献类型：期刊论文
| 作者 | Zhu, Jianming3,4; Li, Xiaolong2; Wang, Guimin3,4; Li, Bo3,4; Xu, Zhijian3,4 ; Tian, Shikai2; Hall, Adrian1; Shen, Jingshan3,4; Shi, Jiye1,5; Zhu, Weiliang3,4
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| 刊名 | SYNTHESIS-STUTTGART
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| 出版日期 | 2016-05 |
| 卷号 | 48期号:9页码:1331-1343 |
| 关键词 | 4-alkoxy-2-oxazoline benzonitrile beta-hydroxyacetal trifluoromethanesulfonic acid reaction mechanism quantum chemistry calculation |
| ISSN号 | 0039-7881 |
| DOI | 10.1055/s-0035-1561386 |
| 文献子类 | Article |
| 英文摘要 | Substituted 4-alkoxy-2-oxazolines have been synthesized via the reaction of nitriles with beta-hydroxyacetals promoted by trifluoromethanesulfonic acid. The reaction is proposed to be initiated by the protonation of the acetals to produce carbocations that are then attacked by nitrogen atom of the nitriles, followed by an intramolecular cyclization reaction to form the 4-alkoxy-2-oxazolines. The proposed reaction mechanism has been validated by quantum chemistry calculations, key intermediate synthesis, and NMR spectra. |
| WOS关键词 | OXAZOLES ; HETEROCYCLES ; AMINATION ; BOND |
| 资助项目 | NNSF[81273435] ; NNSF[81302699] ; National Science & Technology Major Project[2013ZX09103001-001] ; Ministry of Science and Technology[2012AA01A305] ; Natural Science Foundation of Shanghai, China[14ZR1447800] ; State Key Laboratory of Natural and Biomimetic Drugs[K20150205] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000374795500007 |
| 出版者 | GEORG THIEME VERLAG KG |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/276060]  |
| 专题 | 药物发现与设计中心 |
| 通讯作者 | Li, Bo; Shi, Jiye; Zhu, Weiliang |
| 作者单位 | 1.UCB Biopharma SPRL, Chemin Foriest, B-1420 Braine Lalleud, Belgium; 2.Univ Sci & Technol China, Nano Sci & Technol Inst, Suzhou 215123, Peoples R China; 3.Chinese Acad Sci, Shanghai Inst Mat Med, Drug Discovery & Design Ctr, Shanghai 201203, Peoples R China; 4.Chinese Acad Sci, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China; 5.Univ Oxford, Kellogg Coll, 60-62 Banbury Rd, Oxford OX2 6PN, England |
| 推荐引用方式 GB/T 7714 | Zhu, Jianming,Li, Xiaolong,Wang, Guimin,et al. Facile Synthesis of Substituted 4-Alkoxy-2-oxazolines and Exploration of the Reaction Mechanism[J]. SYNTHESIS-STUTTGART,2016,48(9):1331-1343. |
| APA | Zhu, Jianming.,Li, Xiaolong.,Wang, Guimin.,Li, Bo.,Xu, Zhijian.,...&Zhu, Weiliang.(2016).Facile Synthesis of Substituted 4-Alkoxy-2-oxazolines and Exploration of the Reaction Mechanism.SYNTHESIS-STUTTGART,48(9),1331-1343. |
| MLA | Zhu, Jianming,et al."Facile Synthesis of Substituted 4-Alkoxy-2-oxazolines and Exploration of the Reaction Mechanism".SYNTHESIS-STUTTGART 48.9(2016):1331-1343. |
入库方式： OAI收割
来源：上海药物研究所
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