The one-pot synthesis of novel 1,4-disubstituted 1,2,3-triazoles from isoquinoline-substituted homopropargyl alcohol backbone is described (42%-88% yields). A ring closing metathesis reaction and an intramolecular Pauson-Khand reaction of enyne system derived from a homopropargyl alcohol backbone to afford the corresponding isoquinoline-substituted dihydropyran and cyclopentenone-pyran, respectively, are also described (54% and 78% yields). Information about the structural, electronic, and physico-chemical properties of the novel compounds, obtained by density functional theory application, is also reported.