Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 47, Pages 16775-16780Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201503302
Keywords
azides; click chemistry; heterocycles; ketones; organocatalysis
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Funding
- DST (New Delhi)
- CSIR (New Delhi)
- UGC (New Delhi)
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Organocatalytic azide-ketone [3+2] cycloaddition (OrgAKC) of a variety of 1-aryl-2-(arylthio)ethanones and 1-alkyl-2-(alkylthio)ethanones with different aryl or alkyl azides is reported in dimethyl sulfoxide or solvent-free under ambient conditions to furnish 1,5-disubstituted 4-thio-1,2,3-triazoles in a regiospecific manner, which are further converted into useful 1,5-disubstituted 1,2,3-triazoles by treatment with Raney Ni at 25 degrees C for 1-3 h. Notable features of the OrgAKC reaction include high rate and selectivity, solvent-free conditions, easily available substrates and catalysts, a wide range of synthetic and medicinal applications, and excellent yields generating a vast library of triazoles.
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