This research focuses on synthesizing novel tetrahydroquinoline-1,2,3-triazole hybrids as potential agents for neurodegenerative diseases, particularly Alzheimer's disease (AD). The series of structurally distinct hybrid compounds synthesized in this study are previously unreported in the literature. The synthetic strategy involved a diastereoselective imino Diels-Alder reaction (Povarov reaction) to construct the tetrahydroquinoline (THQ) core, where various catalysts, including phthalic acid, lewis acids, KSF (montmorillonite), and ceric ammonium nitrate (CAN), were screened. Phthalic acid was selected as the most efficient catalyst for this crucial step. Following this, efficient click chemistry was employed to introduce the triazole moiety, adhering to green chemistry principles throughout the process. The chemical structure of the synthetized compounds was assigned using analysis of Nuclear Magnetic Resonance (NMR), Mass Spectrometry (MS) and Infrared (IR) spectroscopy. Furthermore, in silico analyses performed with Swiss ADME and OSIRIS Property Explorer indicated that most compounds exhibited excellent drug-like characteristics and favorable pharmacokinetic profiles. The synthesized compounds were evaluated as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) using the modified Ellman's methodology. The inhibitory activity is presented as values for each enzyme and compared to galantamine as a reference standard. These findings offer promising directions for the development of new therapeutic agents for AD based on organic synthesis.