Facile synthesis of 3,5-diaryl-1,2,4-triazoles via copper-catalyzed domino nucleophilic substitution/oxidative cyclization using amidines or imidates as substrates
- Publication Type
- Journal contribution (peer reviewed)
- Authors
- Sudheendran, K; Schmidt, D.; Frey, W.; Conrad, J.; Beifuss, U.
- Year of publication
- 2014
- Published in
- Tetrahedron
- Band/Volume
- 70/
- DOI
- 10.1016/j.tet.2014.01.019
- Page (from - to)
- 1635-1645
Two methods for the synthesis of 3,5-diaryl-1,2,4-triazoles, both domino reactions, are reported. The first procedure, the Cu(OTf)2-catalyzed reaction between two amidines using NaHCO3 as a base, 1,10-phenanthroline as an additive and K3[Fe(CN)6]/ atmospheric oxygen as the oxidant, delivers 3,5-diaryl-1,2,4-triazoles with yields up to 68%. The second procedure for the synthesis of 3,5-diaryl-1,2,4- triazoles with yields up to 64% rests on the Cu(OTf)2-catalyzed reaction between two imidates and ammonium carbonate. This method features the formation of three bonds in a single synthetic step.