Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes?

Organic & Biomolecular Chemistry Pub Date: 2015-03-02 DOI: 10.1039/C5OB00131E

Abstract

PPA-induced umpolung triggers efficient nucleophilic addition of unactivated anilines to nitroalkanes to produce N-hydroxyimidamides. The latter undergo sequential acid-promoted cyclocondensation with ortho-OH or ortho-NHR moieties to afford benzoxazoles and benzimidazoles, respectively.

Graphical abstract: Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes
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