title: Highly regioselective nitrile oxide dipolar cycloadditions with ortho-nitrophenyl alkynes.
abstract: The dipolar cycloadditions of ortho-nitrophenyl alkynes with aryl nitrile oxides has been demonstrated. A range of substituents are tolerated on the alkyne. These reactions proceed with excellent levels of regioselectivity. Subsequent functionalization of the isoxazole scaffold has been demonstrated.
authors.affiliation: Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, Oregon 97331, USA.
authors.forename: Melissa L
authors.initials: ML
authors.lastname: McIntosh
authors.forename: Michael R
authors.initials: MR
authors.lastname: Naffziger
authors.forename: Bradley O
authors.initials: BO
authors.lastname: Ashburn
authors.forename: Lev N
authors.initials: LN
authors.lastname: Zakharov
authors.forename: Rich G
authors.initials: RG
authors.lastname: Carter
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis*; D002384:Catalysis; D061565:Cycloaddition Reaction; D007555:Isoxazoles / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D009570:Nitriles / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D010091:Oximes / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D000577:Amides; D007555:Isoxazoles; D009570:Nitriles; D010087:Oxides; D010091:Oximes