Issue 14, 2015
From the journal:

Organic & Biomolecular Chemistry

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

Alexander V. Aksenov,*a   Alexander N. Smirnov,a   Nicolai A. Aksenov,a   Asiyat S. Bijieva,a   Inna V. Aksenovaa  and  Michael Rubin*ab  

* Corresponding authors

a Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355009, Russian Federation
E-mail: alexaks05@rambler.ru
Tel: +7 (918) 743-0255

b Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr., Lawrence, KS 66045-7582, USA
E-mail: mrubin@ku.edu
Fax: +1 (785) 864-5396
Tel: +1 (785) 864-5071

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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Article information

DOI
https://doi.org/10.1039/C5OB00131E
Article type
Paper
Submitted
22 Jan 2015
Accepted
02 Mar 2015
First published
02 Mar 2015

Org. Biomol. Chem., 2015,13, 4289-4295

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Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes

A. V. Aksenov, A. N. Smirnov, N. A. Aksenov, A. S. Bijieva, I. V. Aksenova and M. Rubin, Org. Biomol. Chem., 2015, 13, 4289 DOI: 10.1039/C5OB00131E

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