Copper‐Catalyzed Click Synthesis of Novel 1,2,3‐Triazole‐Linked Pyrimidines

A series of novel 1,2,3‐triazole‐functionalized pyrimidines were prepared by the reaction of 4‐propargyl‐substituted‐5‐bromo‐2‐chloro‐6‐methylpyrimidine with aryl azides via copper‐catalyzed azide‐alkyne cycloaddition reactions in the presence of phenylenediamine, as a ligand. This method offers the...

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Veröffentlicht in:ChemistrySelect (Weinheim) 2018-03, Vol.3 (9), p.2594-2598
Hauptverfasser: Bakherad, Mohammad, Rezaeimanesh, Fatemeh, Nasr‐Isfahani, Hossein
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Sprache:eng
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Zusammenfassung:A series of novel 1,2,3‐triazole‐functionalized pyrimidines were prepared by the reaction of 4‐propargyl‐substituted‐5‐bromo‐2‐chloro‐6‐methylpyrimidine with aryl azides via copper‐catalyzed azide‐alkyne cycloaddition reactions in the presence of phenylenediamine, as a ligand. This method offers the advantages of mild experimental conditions, operational simplicity, and good to high reaction yields. Furthermore, the synthesized compounds were screened against the three bacterial strains Micrococcus luteus, Pseudomonas aeruginosa, and Bacillus subtilis. An efficient and environmentally benign synthesis of 1,2,3‐triazole functionalized pyrimidines by the reaction of 4‐propargyl‐substituted‐5‐bromo‐2‐chloro‐6‐methylpyrimidines with aryl azides via the copper‐catalyzed click reactions in the presence of phenylenediamine, as a base ligand in ethanol. Mild experimental conditions, short reaction time, easy work‐up, and good‐to‐high yields were some advantages of this method. Their structures are confirmed by NMR spectra as well as elemental analyses.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.201703088