Abstract
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.
Highlights
The 1,4-disubstituted-1,2,3-triazole heterocyclic motif has become an exceedingly popular structure finding applications in a broad range of areas including materials, biomaterials, metallopharmaceuticals, supramolecular chemistry, chemical sensing and catalysis, to name just a few [1]
As part of our endeavor in quinoline-2,4-dione chemistry [10] as well as functional click triazoles [11,12] and their applications [13], we became interested in the synthesis of bis(1,2,3-triazole) functionalized quinoline-2,4-diones 2 that may potentially serve as functional scaffolds in coordination
We reasoned that the desired bis(1,2,3-triazole) functionalized quinoline-2,4-diones 2 could be
Summary
The 1,4-disubstituted-1,2,3-triazole heterocyclic motif has become an exceedingly popular structure finding applications in a broad range of areas including materials, biomaterials, metallopharmaceuticals, supramolecular chemistry, chemical sensing and catalysis, to name just a few [1]. 1,3-cycloaddition of terminal alkynes with organic azides, the CuAAC click reaction, the preparation of 1,4-disubstituted-1,2,3-triazole is facilitated in mild and modular fashion [7,8]. This “click triazole” has become a part of a broad range of molecules, its association with quinoline-2,4-diones remains largely underdeveloped. As part of our endeavor in quinoline-2,4-dione chemistry [10] as well as functional click triazoles [11,12] and their applications [13], we became interested in the synthesis of bis(1,2,3-triazole) functionalized quinoline-2,4-diones 2 that may potentially serve as functional scaffolds in coordination. A general structure of 1,2,3-triazole quinoline-2,4-diones quinoline-2,4-diones 1 (left) and the bis(1,2,3-triazole) counterparts 2 (right)
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