Synthesis of 4,5-disubstituted-1H-1,2,3-triazoles

abstract

Two-step procedure, a palladium catalyzed Sonogashira cross-coupling reaction of aroyl chlorides with aryl acetylenes, and 1,3-dipolar cycloaddition of the 1,3-diarylprop-2-yn-1-ones with sodium azide under catalyst free conditions achieved the synthesis of aryl(4-aryl-1H-1,2,3-triazol-5-yl)methanones in moderate-to-good chemical yields (30-90%). The procedures allowed the synthesis of 4,5-disubstituted-1H-1,2,3-triazol scaffolds containing electron-neutral, -withdrawing, or -donating groups. [GRAPHICS] .

keywords

AZIDE-ALKYNE CYCLOADDITION; ONE-POT SYNTHESIS; CLICK CHEMISTRY; BIOLOGICAL EVALUATION; ACID-CHLORIDES; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; SONOGASHIRA REACTION; PALLADIUM CATALYST; TERMINAL ALKYNES; LIQUID-CRYSTALS

subject category

Chemistry

authors

Rocha, DHA; Pinto, DCGA; Silva, AMS

our authors

acknowledgements

Thanks are due to FCT/MEC for the financial support to the QOPNA research Unit (FCT UID/QUI/00062/2013), through national founds and where applicable co-financed by the FEDER, within the PT2020 Partnership Agreement, and to the Portuguese NMR Network. D. H. A. Rocha also thanks FCT for her Ph.D. Grant (SFRH/BD/68991/2010).

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