ICCAS OpenIR
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
Yu, Nan; Wang, Congyang; Zhao, Fei; Liu, Lantao3; Zhang, Wen-Xiong; Xi, Zhenfeng1,4
2008
Source PublicationCHEMISTRY-A EUROPEAN JOURNAL
ISSN0947-6539
Volume14Issue:18Pages:5670-5679
AbstractAddition 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.
KeywordCyclization Nitrogen Heterocycles Polycycles Silanes Synthetic Methods
DOI10.1002/chem.200701742
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000257574800030
PublisherWILEY-BLACKWELL
Citation statistics
Cited Times:42[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/63210
Collection中国科学院化学研究所
Corresponding AuthorXi, Zhenfeng
Affiliation1.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
Recommended Citation
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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