In this paper, the synthesis of targeted benzothiazole derivatives bridged with a hydrazone coupling (3-14) and 1,2,3-triazole benzothiazole derivatives (17-26) as potentially biologically active agents is described, and their structural characterization by NMR spectroscopy was carried out. 2-amino-6-methoxybenzo[d]thiazole (1) was synthesized by the cyclization reaction of pmethoxyaniline with potassium thiocyanate and bromine in acetic acid, which was then converted into 2-hydrazinyl-6-methoxybenzo[d]thiazole (2) by reaction of nucleophilic substitution with hydrazine hydrate in the presence of ethylene glycol and hydrochloric acid. Benzothiazole hydrazone derivatives (3-14) were prepared by mechanochemical reactions of 2-hydrazinyl-6-methoxybenzo[d]thiazole (2) and corresponding aldehydes. 4-methoxy-3-(prop-2-yn-1-yloxy)benzaldehyde (15) was synthesized by microwave-assisted reaction of O-alkylation of 3-hydroxy-4-methoxybenzaldehyde with propargyl bromide and potassium carbonate as a base. 2-(4-methoxy-3-(prop-2-yn-1-yloxy)phenyl)benzo[d]thiazole (16) was prepared by the condensation reaction of compound 15 and 2-aminothiophenol with sodium metabisulfite as an oxidizing agent in dimethylformamide. 1,2,3-triazole derivatives of benzothiazole (17-26) were synthesized by mechanochemical Huisgen 1,3-dipolar cycloaddition of compound 16 and the corresponding azides in methanol with copper(II) acetate as a catalyst. Structural characterization of the prepared compounds was performed by 1H and 13C-NMR spectroscopy. Pharmacological effects and possible biological targets of the prepared compounds were predicted by in silico analysis.