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An Organocatalytic Regiospecific Synthesis of 1,5‐Disubstituted 4‐Thio‐1,2,3‐triazoles and 1,5‐Disubstituted 1,2,3‐Triazoles
Author(s) -
Ramachary Dhevalapally B.,
Krishna Patoju M.,
Gujral Jagjeet,
Reddy G. Surendra
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503302
Subject(s) - thio , combinatorial chemistry , chemistry , stereochemistry
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 °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.