A general and efficient five-step one-pot procedure leading to nitrogen-bridgehead heterocycles containing an imidazole ring.
A very simple annulation reaction was designed, allowing an imidazole moiety to be fused onto a range of pyridine-based derivatives. The methodology consists of an activation step via the formation of a pyridinium salt to increase the electrophilicity of the pyridine ring, followed by a cascade reaction triggered by a nucleophilic attack of the iminium moiety. Depending on the pyridinium salt, it is possible to obtain functionalized imidazole moieties.
Parenty
Alexis D C
AD
Chemistry Department, WestCHEM, University of Glasgow, Glasgow, United Kingdom.
Song
Yu-Fei
YF
Richmond
Craig J
CJ
Cronin
Leroy
L
D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D007093:Imidazoles; D011725:Pyridines