Synthesis of Bis(1,2,3-Triazole) Functionalized Quinoline-2,4-Diones^†

Derivatives of 3-(1H-1,2,3-triazol-1-yl)quinoline-2,4(1H,3H)-dione unsubstituted on quinolone nitrogen atom, which are available by the previously described four step synthesis starting from aniline, were exploited as intermediates in obtaining the title compounds. The procedure involves the introduction of propargyl group onto the quinolone nitrogen atom of mentioned intermediates by the reaction of them with propargyl bromide in N,N-dimethylformamide (DMF) in presence of a potassium carbonate and the subsequent formation of a second triazole ring by copper catalyzed cyclisation reaction with azido compounds. The products were characterized by ¹H, ¹³C and ¹⁵N NMR spectroscopy. The corresponding resonances were assigned on the basis of the standard 1D and gradient selected 2D NMR experiments (¹H–¹H gs-COSY, ¹H–¹³C gs-HSQC, ¹H–¹³C gs-HMBC) with ¹H–¹⁵N gs-HMBC as a practical tool to determine ¹⁵N NMR chemical shifts at the natural abundance level of ¹⁵N isotope. View Full-Text