Tetrahedron Letters, ( ISI ), Volume (55), No (1), Year (2014-1) , Pages (333-337)

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

Authors: Abbas Ali Esmaeili , Farzaneh Zarifi , Abbas Moradi , Mohammad Izadyar , Ali Reza Fakhari ,

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Novel, one-pot, three-component reactions of the zwitterions generated in situ from pyridine and acety- lenic esters with alkoxymethylenemalononitriles via 1,4-dipolar cycloadditions are described. The reac- tions 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.

Keywords

, Quinolizine, Acetylenic ester, Alkoxymethylenemalononitriles, Pyridine,
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@article{paperid:1037920,
author = {Esmaeili, Abbas Ali and Farzaneh Zarifi and Abbas Moradi and Izadyar, Mohammad and Ali Reza Fakhari},
title = {Diastereoselective synthesis of highly functionalized quinolizines via a pyridine-based three-component reaction and a DFT investigation on the reaction mechanism},
journal = {Tetrahedron Letters},
year = {2014},
volume = {55},
number = {1},
month = {January},
issn = {0040-4039},
pages = {333--337},
numpages = {4},
keywords = {Quinolizine; Acetylenic ester; Alkoxymethylenemalononitriles; Pyridine; DFT},
}

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%0 Journal Article
%T Diastereoselective synthesis of highly functionalized quinolizines via a pyridine-based three-component reaction and a DFT investigation on the reaction mechanism
%A Esmaeili, Abbas Ali
%A Farzaneh Zarifi
%A Abbas Moradi
%A Izadyar, Mohammad
%A Ali Reza Fakhari
%J Tetrahedron Letters
%@ 0040-4039
%D 2014

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