title: Reaction of 1-nitroso-2-naphthols with α-functionalized ketones and related compounds: the unexpected formation of decarbonylated 2-substituted naphtho[1,2-d][1,3]oxazoles.
abstract: Reactions between 1-nitroso-2-naphthols and α-functionalized ketones such as α-bromo-, α-chloro-, α-mesyloxy-, α-tosyloxy-, and α-hydroxy ketones under basic conditions delivered 2-substituted naphtho[1,2-d][1,3]oxazoles in a single synthetic operation. The product formation was accompanied by the unexpected loss of the C═O group from the α-functionalized ketones. With aryl bromides, allyl bromides, α-bromo diketones, α-bromo cyanides, α-bromoesters, and α-bromo ketoesters as substrates the formation of naphtho[1,2-d][1,3]oxazoles was also observed. The transformations were performed in 1,2-dichloroethane or acetonitrile under reflux and gave the corresponding naphthoxazoles with yields ranging between 52% and 85%.
authors.affiliation: Bioorganische Chemie, Institut für Chemie, Universität Hohenheim, Garbenstraße 30, D-70599 Stuttgart, Germany.
authors.forename: Nayyef
authors.initials: N
authors.lastname: Aljaar
authors.forename: Chandi C
authors.initials: CC
authors.lastname: Malakar
authors.forename: Jürgen
authors.initials: J
authors.lastname: Conrad
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Frey
authors.forename: Uwe
authors.initials: U
authors.lastname: Beifuss
mesh_terms: D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry; D009603:Nitroso Compounds / Q000737:chemistry*; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006846:Hydrocarbons, Halogenated; D007659:Ketones; D009284:Naphthols; D009603:Nitroso Compounds; D010080:Oxazoles; D010165:Palladium; C025341:1-nitroso-2-naphthol