title: Expeditive access to 2-substituted 4H-pyrido[1,3]oxazin-4-ones via an intramolecular O-arylation.
abstract: Unreported 2-substituted 4H-pyrido[e][1,3]oxazin-4-ones are synthesized via an unprecedented intramolecular O-arylation of N-aroyl- and N-heteroaroyl-(iso)nicotinamides under microwave irradiations, in good to excellent yields. The broad applicability was demonstrated by 24 examples with a variety of substituents at the 2-position of the final compounds and 3 possible positions for the nitrogen atom of the pyridine ring. In addition, transformation of one of these compounds into 2-hydroxypyridyl-substituted 1,2,4-triazole and 1,2,4-oxazinone was realized. This approach opens a rapid access to a new bicyclic heteroaromatic chemical series with high potential in medicinal chemistry.
authors.affiliation: Sanofi R&D, Exploratory Unit, 1 Avenue Pierre Brossolette, 91385 Chilly Mazarin Cedex, France. franck.slowinski@sanofi.com
authors.forename: Franck
authors.initials: F
authors.lastname: Slowinski
authors.forename: Omar
authors.initials: O
authors.lastname: Ben Ayad
authors.forename: Ozge
authors.initials: O
authors.lastname: Ziyaret
authors.forename: Candice
authors.initials: C
authors.lastname: Botuha
authors.forename: Laetitia
authors.initials: L
authors.lastname: Le Falher
authors.forename: Kamel
authors.initials: K
authors.lastname: Aouane
authors.forename: Serge
authors.initials: S
authors.lastname: Thorimbert
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002626:Chemistry, Pharmaceutical; D010078:Oxazines / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D010078:Oxazines; D011725:Pyridines