title: General synthesis of 2,1-benzisoxazoles (anthranils) from nitroarenes and benzylic C-H acids in aprotic media promoted by combination of strong bases and silylating agents.
abstract: Carbanions of phenylacetonitriles, benzyl sulfones, and dialkyl benzylphosphonates add nitroarenes at the ortho-position to the nitro group to form [Formula: see text]-adducts that, upon treatment with trialkylchlorosilane and additional base (t-BuOK or DBU), transform into 3-aryl-2,1-benzisoxazoles in moderate-to-good yields.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Ul. Kasprzaka 44/52, PO Box 58, 01-224, Warszawa, Poland.
authors.forename: Michał
authors.initials: M
authors.lastname: Wiȩcław
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Ul. Kasprzaka 44/52, PO Box 58, 01-224, Warszawa, Poland.
authors.forename: Mariusz
authors.initials: M
authors.lastname: Bobin
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Ul. Kasprzaka 44/52, PO Box 58, 01-224, Warszawa, Poland.
authors.forename: Andrzej
authors.initials: A
authors.lastname: Kwast
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Ul. Kasprzaka 44/52, PO Box 58, 01-224, Warszawa, Poland.
authors.forename: Robert
authors.initials: R
authors.lastname: Bujok
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Ul. Kasprzaka 44/52, PO Box 58, 01-224, Warszawa, Poland. zwrobel@icho.edu.pl.
authors.forename: Zbigniew
authors.initials: Z
authors.lastname: Wróbel
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Ul. Kasprzaka 44/52, PO Box 58, 01-224, Warszawa, Poland. kwojciechowski@icho.edu.pl.
authors.forename: Krzysztof
authors.initials: K
authors.lastname: Wojciechowski
mesh_terms: D001593:Benzyl Compounds / Q000737:chemistry*; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D001593:Benzyl Compounds; D007555:Isoxazoles; C033962:anthranil
keywords: Aromatic substitution; Carbanions; Cyanides; Elimination; Heterocycles; Nitroarenes; Nucleophilic addition; Nucleophilic substitution