Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes

Organic & Biomolecular Chemistry
Alexander V AksenovMichael Rubin

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.

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Citations

Jul 1, 2017·Organic & Biomolecular Chemistry·Caixia XieChen Ma
Mar 7, 2018·Organic & Biomolecular Chemistry·Qianqian GuanZhiyong Wang
May 29, 2018·Organic & Biomolecular Chemistry·Alexander V AksenovMichael Rubin
Nov 10, 2018·Chemical Communications : Chem Comm·Alexander V AksenovMichael Rubin
May 10, 2019·Organic & Biomolecular Chemistry·Chandan Gharui, Subhas Chandra Pan
Aug 20, 2020·Organic & Biomolecular Chemistry·Nicolai A AksenovAlexander Kornienko
Jul 25, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Alexander V AksenovMichael Rubin
Sep 11, 2019·The Journal of Organic Chemistry·Alexander V AksenovMichael Rubin

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