Novel cycloaddition of nitriles with monolithio- and dilithiobutadienes.
作者： Jinglong Chen , Qiuling Song , Congyang Wang , Zhenfeng Xi
DOI: 10.1021/JA0262176
关键词: Organolithium compounds 、 Cycloaddition 、 Organic chemistry 、 Aliphatic compound 、 Pyridine 、 Regioselectivity 、 Chemistry
摘要: Two novel and synthetically useful reaction patterns of organolithium compounds with nitriles are reported to afford pyridine derivatives as the final products. Both 1-lithio-1,3-dienes 1,4-dilithio-1,3-dienes, which can be easily generated in situ by lithiation their corresponding iodo compounds, react presence HMPA form substituted pyridines including 2,2‘-bipyridines tetrahydroisoquinolines high yields.
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sci-hub.se 参考文章(8)
Chanjuan Xi, Shouquan Huo, Tarek Hassan Afifi, Ryuichiro Hara, Tamotsu Takahashi, Remarkable effect of copper chloride on diiodination of zirconacyclopentadienes Tetrahedron Letters. ,vol. 38, pp. 4099- 4102 ,(1997) , 10.1016/S0040-4039(97)00835-6
Tamotsu Takahashi, Wen-Hua Sun, Chanjuan Xi, Ubayama Haruka, Zhenfeng Xi, Selective one carbon-carbon bond formation reaction of zirconacyclopentadienes with aryl iodides or alkynyl iodides Tetrahedron. ,vol. 54, pp. 715- 726 ,(1998) , 10.1016/S0040-4020(97)10295-2
Zhenfeng Xi, Qiuling Song, Jinglong Chen, Hairong Guan, Pixu Li, Dialkenylation of Carbonyl Groups by Alkenyllithium Compounds: Formation of Cyclopentadiene Derivatives by the Reaction of 1,4-Dilithio-1,3-dienes with Ketones and Aldehydes Angewandte Chemie International Edition. ,vol. 40, pp. 1913- 1916 ,(2001) , 10.1002/1521-3773(20010518)40:10<1913::AID-ANIE1913>3.0.CO;2-N
Zhenfeng Xi, Qiuling Song, Efficient synthesis of cyclopentadienone derivatives by the reaction of carbon dioxide with 1,4-dilithio-1,3-dienes Journal of Organic Chemistry. ,vol. 65, pp. 9157- 9159 ,(2000) , 10.1021/JO005641R
Jesús A. Varela, Luis Castedo, Carlos Saá, One-Step Synthesis of Symmetrical 3,3‘-Substituted 2,2‘-Bipyridine Ligands by Cobalt(I)-Catalyzed [2 + 2 + 2] Cycloadditions Journal of the American Chemical Society. ,vol. 120, pp. 12147- 12148 ,(1998) , 10.1021/JA982832R
Jan Pawlas, Per Vedsø, Palle Jakobsen, Per Olaf Huusfeldt, Mikael Begtrup, Novel Anionic Annelation Tactics for Construction of Fused Heteroaromatic Frameworks. 1. Synthesis of 4-Substituted Pyrazolo[4,3-c]quinolines, 9-Substituted Pyrazolo[3,4-c]quinolines, and 1,4-Dihydrochromeno[4,3-c]pyrazoles Journal of Organic Chemistry. ,vol. 66, pp. 4214- 4219 ,(2001) , 10.1021/JO001422U
Qiuling Song, Jinglong Chen, Xianglin Jin, Zhenfeng Xi, Highly regio- and stereoselective 1,1-cycloaddition of carbon monoxide with 1,4-dilithio-1,3-dienes. Novel synthetic methods for 3-cyclopenten-1-one derivatives. Journal of the American Chemical Society. ,vol. 123, pp. 10419- 10420 ,(2001) , 10.1021/JA0165638
Morten Lysén, Jesper L. Kristensen, Per Vedsø, Mikael Begtrup, Convergent synthesis of 6-substituted phenanthridines via anionic ring closure. Organic Letters. ,vol. 4, pp. 257- 259 ,(2002) , 10.1021/OL0170051