Synthesis of Substituted Pyridines from Cascade [1+5] Cycloaddition of Isonitriles to N-Formylmethyl-Substituted Enamides, Aerobic Oxidative Aromatization, and Acyl Transfer Reaction
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 | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
 |
| 出版日期 | 2013-03-27 |
| 卷号 | 135期号:12页码:4708-4711 |
| ISSN号 | 0002-7863 |
| DOI | 10.1021/ja401701x |
| 英文摘要 | A novel strategy for de novo synthesis of pyridines featuring an unprecedented a-addition of aldehyde and enamide to isonitrile as a key step is described. Under mild conditions, a cascade reaction involving Zn(OTf)(2)-promoted [1 + 5] cycloaddition of isonitrile with N-formylmethyl-substituted enamide, facile aerobic oxidative aromatization and intermolecular acyl transfer from the pyridinium nitrogen to the 5-hydroxy oxygen, and finally acylation of the 4-amino group by an external acyl chloride efficiently afforded 2-substituted 4-acylamino-5-acyloxypyridines in good to excellent yields. |
| 语种 | 英语 |
| WOS记录号 | WOS:000317032000034 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/54815]  |
| 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, Minist Educ, Key Lab Bioorgan Phosphorous & Chem Biol, Beijing 100084, Peoples R China 3.Ecole Polytech Fed Lausanne, EPFL SB ISIC LSPN, Inst Chem Sci & Engn, BCH 5304, 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 Substituted Pyridines from Cascade [1+5] Cycloaddition of Isonitriles to N-Formylmethyl-Substituted Enamides, Aerobic Oxidative Aromatization, and Acyl Transfer Reaction[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2013,135(12):4708-4711. |
| APA | Lei, Chuan-Hu,Wang, De-Xian,Zhao, Liang,Zhu, Jieping,&Wang, Mei-Xiang.(2013).Synthesis of Substituted Pyridines from Cascade [1+5] Cycloaddition of Isonitriles to N-Formylmethyl-Substituted Enamides, Aerobic Oxidative Aromatization, and Acyl Transfer Reaction.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,135(12),4708-4711. |
| MLA | Lei, Chuan-Hu,et al."Synthesis of Substituted Pyridines from Cascade [1+5] Cycloaddition of Isonitriles to N-Formylmethyl-Substituted Enamides, Aerobic Oxidative Aromatization, and Acyl Transfer Reaction".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 135.12(2013):4708-4711. |
入库方式： OAI收割
来源：化学研究所
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