title: Solution-phase synthesis of a diverse library of benzisoxazoles utilizing the [3 + 2] cycloaddition of in situ-generated nitrile oxides and arynes.
abstract: A library of benzisoxazoles has been synthesized by the [3 + 2] cycloaddition of nitrile oxides with arynes and further diversified by acylation/sulfonylation and palladium-catalyzed coupling processes. The eight key intermediate benzisoxazoles have been prepared by the reaction of o-(trimethylsilyl)aryl triflates and chlorooximes in the presence of CsF in good to excellent yields under mild reaction conditions. These building blocks have been used as the key components of a diverse set of 3,5,6-trisubstituted benzisoxazoles.
authors.affiliation: Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
authors.forename: Anton V
authors.initials: AV
authors.lastname: Dubrovskiy
authors.forename: Prashi
authors.initials: P
authors.lastname: Jain
authors.forename: Feng
authors.initials: F
authors.lastname: Shi
authors.forename: Gerald H
authors.initials: GH
authors.lastname: Lushington
authors.forename: Conrad
authors.initials: C
authors.lastname: Santini
authors.forename: Patrick
authors.initials: P
authors.lastname: Porubsky
authors.forename: Richard C
authors.initials: RC
authors.lastname: Larock
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D061565:Cycloaddition Reaction; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry*; D010087:Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C441200:1,2-benzisoxazole; D001555:Benzene Derivatives; D007555:Isoxazoles; D009570:Nitriles; D010087:Oxides; D054852:Small Molecule Libraries; C524146:benzyne; D010165:Palladium