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

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.


Keywords


triazoles; barbituric derivatives; DFT study; mechanism

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

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