The search for new bioactive molecules begins with its relevance in the literature, such as coumarin and 1,2,3-triazole systems, which have numerous individual biological properties, especially against cancer. Thus, the objective of this work is to obtain new coumarin-triazole hybrids, seeking a good relationship between structure and antitumor activity. It is intended to investigate how the junction of such systems can influence the activity of these new molecules, more specifically in relation to oral squamous cells (OSCC). To obtain hybrids 6, it was initially necessary to synthesize intermediates 3, 4a-d and 5a. The azide compounds 3 were obtained from 4-hydroxycoumarin (1) in an alkylation reaction with dibromoalkane and followed by a nucleophilic bimolecular substitution with sodium azide. Compounds 3 were obtained in good yields (72-74%). Propargylated naphthoquinones 4a-d were obtained via propargylation with propargyl bromide or propargylamine from commercial naphthoquinones obtaining the derivatives in moderate yields (40-80%). Propargylated coumarin 5a was obtained in 89% yield via propargylation of 4-hydroxycoumarin with propargyl bromide. Intermediates 3 were reacted with alkynes 4a-d, 5a, 5b-d (commercial) through a 1,3-dipolar cycloaddition reaction catalyzed by Cu(I) obtaining 16 hybrids 6 with yields varying from 30-65 %. Their structures were confirmed using different physical analysis methods - NMR, IR and HRMS. Subsequently, the substances will have their biological activity evaluated against oral squamous cell carcinoma (OSCC).