期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2014, 期 36, 页码 8167-8181出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201403100
关键词
Nitrogen heterocycles; Click chemistry; Ligand design; NMR spectroscopy
资金
- Ministry of Education, Science, and Sport, Republic of Slovenia
- Slovenian Research Agency [P1-0230]
A combinatorial modular approach based on the click copper(I)-catalysed azide-alkyne cycloaddition reaction was used to prepare a library of selected 1,4-disubstituted 1,2,3-triazoles differently functionalized with heteroaryl groups including pyridine, pyrimidine, and pyrazine. Three different copper(I) sources, i.e., CuSO4/sodium ascorbate, CuBr(PPh3)(3), and (CuOTf)(2)center dot C6H6 were used to promote the coupling reactions of a range of aryl, heteroaryl, and heteroarylmethyl azides with alkyne click partners. As the target heteroaryl triazoles were designed to serve as advanced ligands or ligand precursors for metal coordination, they were fully characterized by H-1, C-13, and N-15 NMR spectroscopy. The resonances were assigned on the basis of 1D and 2D NMR experiments. H-1-N-15 gs-HMBC was used as a practical tool to determine N-15 NMR chemical shifts at the natural abundance level of the N-15 isotope.
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