Ipso- or cine-substitutions of 6-haloimidazo[1,2-a]pyridine derivatives with different azoles depending on the reaction conditions.
The reactivity of 6-haloimidazo[1,2-a]pyridine toward different azoles is reported. The process was shown to be highly dependent on the reaction conditions. Using copper(I) catalyst, the product of ipso substitution was obtained. In the absence of copper, with cesium carbonate in N,N-dimethylformamide, a cine substitution took place.
Enguehard
Cécile
C
EA 3247, Laboratoire de Chimie Thérapeutique, and Laboratoire de Chimie Physique, UFR des Sciences Pharmaceutiques, 31 Avenue Monge, 37200 Tours, France.
Allouchi
Hassan
H
Gueiffier
Alain
A
Buchwald
Stephen L
SL
D001393:Azoles / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D006219:Halogens / Q000737:chemistry; D006993:Hypnotics and Sedatives / Q000138:chemical synthesis*; D011743:Pyrimidines / Q000138:chemical synthesis*
D001393:Azoles; D006219:Halogens; D006993:Hypnotics and Sedatives; D011743:Pyrimidines; D003300:Copper