Diverse reactions of 1,4-dilithio-1,3-dienes with nitriles: Facile access to tricyclic Delta(1)-bipyrrolines, multiply substituted pyridines, siloles, and (Z,Z)-Dienylsilanes by tuning of substituents on the butadienyl skeleton
文献类型：期刊论文
| 作者 | Yu, Nan; Wang, Congyang; Zhao, Fei; Liu, Lantao3; Zhang, Wen-Xiong; Xi, Zhenfeng1,4 |
| 刊名 | CHEMISTRY-A EUROPEAN JOURNAL
 |
| 出版日期 | 2008 |
| 卷号 | 14期号:18页码:5670-5679 |
| 关键词 | Cyclization Nitrogen Heterocycles Polycycles Silanes Synthetic Methods |
| ISSN号 | 0947-6539 |
| DOI | 10.1002/chem.200701742 |
| 英文摘要 | Addition cyclization of 1,2,3,4-tetrasubstituted 1,4-dilithio-1,3-dienes (Type 1) with four equivalents of various aromatic nitriles in the presence of hexamethylphosphoramide (HMPA) gives exclusively fully substituted pyridines in moderate to good yields. Similarly, trisubstituted pyridines can be prepared by the reaction of 2,3-dialkyl- or diaryl-substituted 1,4-dilithio-1,3-dienes (Type II) with nitriles. However, five- or six-membered ring fused 2,3-disubstituted 1,4-dilithio-1,3-dienes (Type III) reacted with various aromatic and aliphatic nitriles without a-hydrogen atoms to afford tricyclic Delta(1)-bipyrrolines in high yields. The reaction of six-membered-ring fused 2,3-disubstituted 1,4-dilithio-1,3-diene (Type III) with 2-cyanopyridine afforded the corresponding pyridine, and no tricyclic Delta(1)-bipyrroline was observed. Seven-membered-ring fused dilithio-dienes reacted with PhCN or trimethylacetonitrile to afford the corresponding pyridines in good yield. When 1,2,3,4-tetrasubstituted dilithio reagents (Type I) were treated with Me(3)SiCN, a tandem silylation/intramolecular substitution process readily occurred to yield siloles, whereas the reaction of 2,3-disubstituted dilithio reagents (Types II and III) with Me(3)SiCN gave rise to (Z,Z)-dienylsilanes with high stereoselectivity. These results revealed that the formation of tricyclic Delta(1)-bipyrrolines, pyridines, siloles, and (Z,Z)-dienylsilanes are strongly dependent on the substitution patterns of the dilithio butadienes and the nature of the nitriles employed. |
| 语种 | 英语 |
| WOS记录号 | WOS:000257574800030 |
| 出版者 | WILEY-BLACKWELL |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/63209]  |
| 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, Key Laboratorv Bioorgan Chem, BNLMS, Beijing 100871, Peoples R China 2.Peking Univ, Mol Engn Minist Educ, Coll Chem, Beijing 100871, Peoples R China 3.Chinese Acad Sci, Inst Chem, Beijing 100080, Peoples R China 4.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China |
| 推荐引用方式 GB/T 7714 | Yu, Nan,Wang, Congyang,Zhao, Fei,et al. Diverse reactions of 1,4-dilithio-1,3-dienes with nitriles: Facile access to tricyclic Delta(1)-bipyrrolines, multiply substituted pyridines, siloles, and (Z,Z)-Dienylsilanes by tuning of substituents on the butadienyl skeleton[J]. CHEMISTRY-A EUROPEAN JOURNAL,2008,14(18):5670-5679. |
| APA | Yu, Nan,Wang, Congyang,Zhao, Fei,Liu, Lantao,Zhang, Wen-Xiong,&Xi, Zhenfeng.(2008).Diverse reactions of 1,4-dilithio-1,3-dienes with nitriles: Facile access to tricyclic Delta(1)-bipyrrolines, multiply substituted pyridines, siloles, and (Z,Z)-Dienylsilanes by tuning of substituents on the butadienyl skeleton.CHEMISTRY-A EUROPEAN JOURNAL,14(18),5670-5679. |
| MLA | Yu, Nan,et al."Diverse reactions of 1,4-dilithio-1,3-dienes with nitriles: Facile access to tricyclic Delta(1)-bipyrrolines, multiply substituted pyridines, siloles, and (Z,Z)-Dienylsilanes by tuning of substituents on the butadienyl skeleton".CHEMISTRY-A EUROPEAN JOURNAL 14.18(2008):5670-5679. |
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来源：化学研究所
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