Cycloaddition reactions of 1-lithio-1,3-dienes with aromatic nitriles affording multiply substituted pyridines, pyrroles, and linear butadienylimines
文献类型：期刊论文
| 作者 | Wang, Congyang; Wang, Zhihui; Liu, Lantao; Wang, Chao; Liu, Guangzhen; Xi, Zhenfeng |
| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2006-10-27 |
| 卷号 | 71期号:22页码:8565-8571 |
| ISSN号 | 0022-3263 |
| DOI | 10.1021/jo061574a |
| 英文摘要 | Fully or partially substituted 1-iodo- or 1-bromo-1,3-dienes could be readily lithiated using t-BuLi or n-BuLi to afford their corresponding 1-lithio-1,3-diene derivatives in quantitative yields. When these in situ generated lithium reagents were treated with organonitriles, depending on the substitution patterns of the butadienyl skeletons, substituted pyridines, pyrroles, and/or linear butadienyl imines were formed in good to excellent yields via N-lithioketimine intermediates. In the cases of 1,2,3,4-tetrasubstituted and 2,3-disubstituted 1-lithio-1,3-dienes, pyridine derivatives or linear butadienyl imines were generally formed depending on the reaction temperatures. When 1,2,3,4-tetrasubstituted 4-halo-1-lithio-1,3-dienes and 1,2-disubstituted 1-lithio-1,3-dienes were treated with organonitriles, pyrrole derivatives or linear butadienyl imines were obtained. Competition between 5-exo and 6-endo cyclization was found to be responsible for the formation of either pyrroles or pyridines. Selective elimination of RLi from the lithiated cyclic N-containing intermediates was observed. The order of elimination was found to be LiCl > Me3SiLi > LiH. |
| 语种 | 英语 |
| WOS记录号 | WOS:000241435600033 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/59613]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Xi, Zhenfeng |
| 作者单位 | 1.Peking Univ, Beijing Natl Lab Mol Sci, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China 2.Chinese Acad Sci, Inst Chem, Beijing 100080, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China |
| 推荐引用方式 GB/T 7714 | Wang, Congyang,Wang, Zhihui,Liu, Lantao,et al. Cycloaddition reactions of 1-lithio-1,3-dienes with aromatic nitriles affording multiply substituted pyridines, pyrroles, and linear butadienylimines[J]. JOURNAL OF ORGANIC CHEMISTRY,2006,71(22):8565-8571. |
| APA | Wang, Congyang,Wang, Zhihui,Liu, Lantao,Wang, Chao,Liu, Guangzhen,&Xi, Zhenfeng.(2006).Cycloaddition reactions of 1-lithio-1,3-dienes with aromatic nitriles affording multiply substituted pyridines, pyrroles, and linear butadienylimines.JOURNAL OF ORGANIC CHEMISTRY,71(22),8565-8571. |
| MLA | Wang, Congyang,et al."Cycloaddition reactions of 1-lithio-1,3-dienes with aromatic nitriles affording multiply substituted pyridines, pyrroles, and linear butadienylimines".JOURNAL OF ORGANIC CHEMISTRY 71.22(2006):8565-8571. |
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。