TY - JOUR
T1 - Facile synthesis of 3,5-diaryl-1,2,4-triazoles via copper-catalyzed domino nucleophilic substitution/oxidative cyclization using amidines or imidates as substrates
AU - Sudheendran, Kavitha
AU - Schmidt, Dietmar
AU - Frey, Wolfgang
AU - Conrad, Jürgen
AU - Beifuss, Uwe
PY - 2014/2/25
Y1 - 2014/2/25
N2 - 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.
AB - 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.
KW - 1,2,4-Triazole
KW - Amidine
KW - Catalysis
KW - Copper
KW - Imidate
UR - http://www.scopus.com/inward/record.url?scp=84893511872&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2014.01.019
DO - 10.1016/j.tet.2014.01.019
M3 - Article
AN - SCOPUS:84893511872
SN - 0040-4020
VL - 70
SP - 1635
EP - 1645
JO - Tetrahedron
JF - Tetrahedron
IS - 8
ER -