Abstract

In recent years, the synthesis of new heterocyclic compounds and their derivatives has significantly increased. The 1,2,4-triazolidine-3-thione scaffold has attracted considerable interest because of its potential applications in pharmaceuticals, agrochemicals, and other biologically relevant areas. This study reports a procedure for synthesizing 1,2,4-triazolidine-3-thione derivatives from aldehydes or ketones and thiosemicarbazide at room temperature, using surface-modified graphene oxide (GO) catalysts to improve reaction efficiency, denoted as GO/APTES/DCDA/Fe³⁺. The structure and properties of the catalyst were determined using modern analytical methods such as FT-IR, SEM, EDS, XRD, Raman, TGA, XPS and ICP-MS, demonstrating its stability and high activity for the synthesis of 1,2,4-triazolidine-3-thione derivatives. The application of GO/APTES/DCDA/Fe³⁺ as a catalyst in the synthesis of 5-aryl-1,2,4-triazolidine-3-thione achieved yields up to 93 %. Furthermore, an in-depth kinetic investigation was concurrently performed to firmly establish the high performance of the catalyst in the newly developed reaction protocol. The calculated thermodynamic parameters (ΔH^‡ = 0.191 kJ mol⁻¹, ΔS^‡ = −0.051 kJ mol⁻¹K⁻¹, ΔG^‡ gradually increases with increasing temperature) were also determined. The catalyst is recyclable – it can be recovered by a simple procedure and reused multiple times. In addition, the carbon precursor was obtained from cassava stem waste, highlighting the protocol’s contribution to green chemistry and sustainability.

Graphical abstract