An efficient synthesis of novel triazoles incorporating barbituric motifs via [3+2] cycloaddition reactions: An experimental and theoretical study

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Mahdieh Darroudi
Yaghoub Sarrafi
Mahshid Hamzehloueian

Abstract

In this work, the synthesis of novel triazole derivatives with barbi­turic motifs in good yields is described. The alkyne was prepared through the Knoevenagel reaction of barbituric derivatives with ortho and para O-propar­gylated hydroxybenzaldehyde. The mechanism and regioselectivity of this [3+2] cycloaddition reaction were investigated using the density func­tional theory at the B3LYP/6-31+G(d) level of theory. The comput­ational studies revealed that a di-copper catalyzed stepwise mechanism, involving six-mem­bered ring intermediate, is the preferred pathway. The regioselectivity was exp­lained in terms of frontier molecular orbital (FMO) interactions, local and glo­bal electrophilicity and nucleophilicity indices. Accordingly, the favored inter­actions for di-copper acetylide are in good agreement with the observed regio­selectivity, while completely opposite results were obtained for a possible uncatalysed reaction.

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How to Cite
[1]
M. Darroudi, Y. Sarrafi, and M. Hamzehloueian, “An efficient synthesis of novel triazoles incorporating barbituric motifs via [3+2] cycloaddition reactions: An experimental and theoretical study”, J. Serb. Chem. Soc., vol. 83, no. 7-8, pp. 821–835, Aug. 2018.
Section
Theoretical Chemistry
Author Biographies

Mahdieh Darroudi, PhD in Organic Chemistry, Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, 47416 Babolsar

Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran,

Mahshid Hamzehloueian, Assistant Professor of Organic Chemistry Department of Chemistry, Jouybar Branch, Islamic Azad University, Jouybar

Assistant Professor of Organic Chemistry

Department of Chemistry, Jouybar Branch, Islamic Azad University, Jouybar, Iran

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