Synthesis of Multifunctionalized 1,2,3,4-Tetrahydropyridines, 2,3-Dihydropyridin-4(1H)-ones, and Pyridines from Tandem Reactions Initiated by [5+1] Cycloaddition of N-Formylmethyl-Substituted Enamides to Isocyanides: Mechanistic Insight and Synthetic Application
文献类型：期刊论文
| 作者 | Lei, Chuan-Hu1; Wang, De-Xian1; Zhao, Liang2; Zhu, Jieping3; Wang, Mei-Xiang2 |
| 刊名 | CHEMISTRY-A EUROPEAN JOURNAL
 |
| 出版日期 | 2013-12-09 |
| 卷号 | 19期号:50页码:16981-16987 |
| 关键词 | Cyanides Cycloaddition Enamides Heterocycles Reaction Mechanisms |
| ISSN号 | 0947-6539 |
| DOI | 10.1002/chem.201303221 |
| 英文摘要 | Tandem reactions for the efficient synthesis of multifunctionalized 1,2,3,4-tetrahydropyridines, 2,3-dihydropyridin-4(1H)-ones, and pyridine derivatives have been developed and reaction mechanisms have been investigated. Synthetic cascades are initiated by the Zn(OTf)(2)-mediated [5+1] cycloaddition of N-formylmethyl-substituted tertiary enamides to isocyanides, thus leading to the versatile heterocyclic enamino imine intermediates. Interception of the intermediates by diastereoselective reduction of imine functionality with Me4NBH(OAc)(3) afforded 1,6-disubstituted trans-3-hydroxy-4-arylamino- or -alkylamino-1,2,3,4-tetrahydropyridines, whereas acylation of the imino group followed by acidic hydrolysis produced 1,6-disubstituted 3-acyloxy-2,3-dihydropyridin-4(1H)-ones. Aerobic oxidation led to the aromatization followed by intermolecular acyl-group transfer from the pyridinium nitrogen to the 3-hydroxy moiety, thereby yielding substituted 3-acyloxy-4-aminopyridines. Synthetic potentials of the resulting products have been demonstrated by expedient and highly stereoselective synthesis of cis,cis-4,5-dihydroxy-2-phenylpiperidine and trans,trans-4-amino-5-hydroxy-2-phenylpiperidine compounds, which are important in medicinal chemistry, through simple and practical reduction reactions. |
| 语种 | 英语 |
| WOS记录号 | WOS:000327801800018 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/53907]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Wang, Mei-Xiang |
| 作者单位 | 1.Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China 2.Tsinghua Univ, Key Lab Bioorgan Phosphorous Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China 3.Ecole Polytech Fed Lausanne, EPFL SB ISIC LSPN, Inst Chem Sci & Engn, CH-1015 Lausanne, Switzerland |
| 推荐引用方式 GB/T 7714 | Lei, Chuan-Hu,Wang, De-Xian,Zhao, Liang,et al. Synthesis of Multifunctionalized 1,2,3,4-Tetrahydropyridines, 2,3-Dihydropyridin-4(1H)-ones, and Pyridines from Tandem Reactions Initiated by [5+1] Cycloaddition of N-Formylmethyl-Substituted Enamides to Isocyanides: Mechanistic Insight and Synthetic Application[J]. CHEMISTRY-A EUROPEAN JOURNAL,2013,19(50):16981-16987. |
| APA | Lei, Chuan-Hu,Wang, De-Xian,Zhao, Liang,Zhu, Jieping,&Wang, Mei-Xiang.(2013).Synthesis of Multifunctionalized 1,2,3,4-Tetrahydropyridines, 2,3-Dihydropyridin-4(1H)-ones, and Pyridines from Tandem Reactions Initiated by [5+1] Cycloaddition of N-Formylmethyl-Substituted Enamides to Isocyanides: Mechanistic Insight and Synthetic Application.CHEMISTRY-A EUROPEAN JOURNAL,19(50),16981-16987. |
| MLA | Lei, Chuan-Hu,et al."Synthesis of Multifunctionalized 1,2,3,4-Tetrahydropyridines, 2,3-Dihydropyridin-4(1H)-ones, and Pyridines from Tandem Reactions Initiated by [5+1] Cycloaddition of N-Formylmethyl-Substituted Enamides to Isocyanides: Mechanistic Insight and Synthetic Application".CHEMISTRY-A EUROPEAN JOURNAL 19.50(2013):16981-16987. |
入库方式： OAI收割
来源：化学研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。