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<p>An efficient and straightforward approach for synthesizing 1,3,5-trisubstituted 1,2,4-triazole derivatives <b>5</b><sup><b>a-d</b></sup>, <b>7</b><sup><b>a-d</b></sup>, and <b>8</b><sup><b>a-c</b></sup>, has been developed through a simple and selective condensation of N-functionalized imidates with two hydrazine derivatives, resulting in moderate to high yields. Our study demonstrates that the choice of hydrazine significantly impacts the reaction selectivity. NMR experiments and theoretical calculations confirmed the formation of the most kinetically and thermodynamically stable product. A detailed DFT investigation at the B3LYP/6-31+G(d) level, complemented by Fukui function analyses, provides deeper insights into the reaction pathway and local reactivity of key intermediates. Additionally, in silico investigations, including molecular docking studies and ADMET profiling, were conducted to highlight the significance of our synthetic strategy, revealing that some triazoles exhibit high predicted antiviral potential.</p> Graphical Abstract <p>This study highlights a selective synthetic pathway for 1,3,5-trisubstituted triazoles with antiviral properties, supported by both experimental and in silico analyses.</p> <p></p>

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Exploring the Synthesis of Trisubstituted 1,2,4-Triazoles from Functionalized Imidates: Experimental and Theoretical Approaches

  • 期刊论文

  • 发表日期：

    2025年4月25日

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  • Oumayma Ben Jaballah,
  • Imen Ferchichi,
  • Safa Azzouni,
  • Mabrouk Horchani,
  • Hichem Ben Jannet,
  • Youssef Arfaoui,
  • Mohamed Lotfi Efrit

摘要

An efficient and straightforward approach for synthesizing 1,3,5-trisubstituted 1,2,4-triazole derivatives 5a-d, 7a-d, and 8a-c, has been developed through a simple and selective condensation of N-functionalized imidates with two hydrazine derivatives, resulting in moderate to high yields. Our study demonstrates that the choice of hydrazine significantly impacts the reaction selectivity. NMR experiments and theoretical calculations confirmed the formation of the most kinetically and thermodynamically stable product. A detailed DFT investigation at the B3LYP/6-31+G(d) level, complemented by Fukui function analyses, provides deeper insights into the reaction pathway and local reactivity of key intermediates. Additionally, in silico investigations, including molecular docking studies and ADMET profiling, were conducted to highlight the significance of our synthetic strategy, revealing that some triazoles exhibit high predicted antiviral potential.

Graphical Abstract

This study highlights a selective synthetic pathway for 1,3,5-trisubstituted triazoles with antiviral properties, supported by both experimental and in silico analyses.