The aim of this work was the regioselective synthesis of novel 4-phenyl-1,2,3-triazolyl substituted benzimidazo[1,2-a]quinolines (3−6, 11, 12) with potential antitumor activity. For this purpose, 5-chlorobenzimidazo[1,2-a]quinoline-6-carbonitrile (1) and its 2-chloro and 2-fluoro derivatives (7, 9) were converted to the corresponding azido derivatives of benzimidazo[1,2-a]quinoline 2, 8 and 10. 1,2,3-Triazole derivatives of benzimidazo[1,2-a]quinoline 3−6, 11 and 12 were then prepared using 1,3-dipolar cycloaddition reaction of the corresponding azide derivative (2, 8, 10) and corresponding terminal alkynes with Cu(I), as a catalyst, following the concept of ´click´ chemistry. In order to obtain better overall yield of the target compounds, two synthetic pathways were used in the synthesis of compounds 4, 5 and 6. First pathway included the conversion of the 5-chlorobenzimidazo[1,2-a]quinoline-6-carbonitrile (1) to the azide 2, its isolation and then a ´click´ reaction of the azide 2 and the corresponding alkynes to form 1,4-disubstituted 1,2,3-triazole derivatives of benzimidazo[1,2-a]quinoline (3−6). Second synthetic pathway was a tandem reaction in which the azido derivative 2 was not isolated, but in situ reacted with the corresponding terminal alkynes to afford, 1,4-disubstituted 1,2,3-triazole derivatives of benzimidazo[1,2-a]quinoline 4, 5 and 6. The reactions were performed at reflux, and the reaction products were isolated by column chromatography. The structures of all compounds have been confirmed by 1H and 13C NMR spectroscopy.