4.5 Article

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

Journal

MOLECULAR DIVERSITY
Volume 19, Issue 4, Pages 807-816

Publisher

SPRINGER
DOI: 10.1007/s11030-015-9627-x

Keywords

Carbanions; Heterocycles; Nucleophilic substitution; Aromatic substitution; Nucleophilic addition; Elimination; Cyanides; Nitroarenes

Funding

  1. National Scientific Center [2012/07/B/ST5/00813]

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Carbanions of phenylacetonitriles, benzyl sulfones, and dialkyl benzylphosphonates add nitroarenes at the ortho-position to the nitro group to form -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.

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