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

Mahdieh Darroudi, Yaghoub Sarrafi, Mahshid Hamzehloueian

Abstract


In this work, synthesis of novel triazole derivatives with barbituric motifs in good yields was described. The alkyne was prepared through Knoevenagel reaction of barbituric derivatives with ortho and para O-propargylated hydroxyl-benzaldehyde. Mechanism and regioselectivity of this [3+2] cycloaddition (CA) reaction were investigated using density functional theory (DFT) 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 most preferred pathway. The regioselectivity has been explained in terms of frontier molecular orbital (FMO) interactions, local and global electrophilicity and nucleophilicity indices. Accordingly, the favoured interactions for di-copper acetylide are in good agreement with the observed regioselectivity, while completely opposite results are obtained for possible uncatalysed reaction.

Keywords


triazoles; barbituric derivatives; DFT study; mechanism

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DOI: https://doi.org/10.2298/JSC170618038D

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