Diastereoselective synthesis of highly functionalized quinolizines via a pyridine-based three-component reaction and a DFT investigation on the reaction mechanism

详细信息    查看全文

• 作者：Abbas Ali Esmaeili ; Farzaneh Zarifi ; Abbas Moradi ; Mohammad Izadyar ; Ali Reza Fakhari
• 关键词：Quinolizine ; Acetylenic ester ; Alkoxymethylenemalononitriles ; Pyridine ; DFT
• 刊名：Tetrahedron Letters
• 出版年：8 January, 2014
• 年：2014
• 卷：55
• 期：2
• 页码：333-337
• 全文大小：751 K

文摘

Novel, one-pot, three-component reactions of the zwitterions generated in situ from pyridine and acetylenic esters with alkoxymethylenemalononitriles via 1,4-dipolar cycloadditions are described. The reactions afforded dialkyl 1,1-dicyano-2-alkoxy-1,9a-dihydro-2H-quinolizine-3,4-dicarboxylate derivatives in good to high yields without using any catalyst or activation. Structural, electronic, energetic, and mechanistic details of the reaction are also revealed by density functional theory (DFT) calculations, which strongly support the exclusive formation of the observed products.