title: Triflic anhydride mediated synthesis of imidazo[1,5-a]azines.
abstract: Imidazo[1,5-a]azines are synthesized in moderate to excellent yields using a mild cyclodehydration/aromatization reaction triggered by the use of triflic anhydride (Tf2O) and 2-methoxypyridine (2-MeOPyr). Various substitution patterns and functional groups were found to be compatible under the optimized conditions. In addition, a 5-bromo-3-aryl derivative was also shown to be active in a Sonogashira cross-coupling and direct arylation reactions. A tertiary amide was compatible as a substrate leading to the synthesis of an imidazo[1,5-a]pyridinium triflate.
authors.affiliation: Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada, H3C 3J7.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Pelletier
authors.forename: André B
authors.initials: AB
authors.lastname: Charette
mesh_terms: D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D005663:Furans; D007093:Imidazoles; D011726:Pyridinium Compounds; D013449:Sulfonamides; C583655:imidazo(1,5-a)pyridinium triflate; C474725:triflic anhydride