Issue 88, 2015
From the journal:

RSC Advances

One-pot synthesis of benzoxazoles via the metal-free ortho-C–H functionalization of phenols with nitroalkanes†

Nicolai A. Aksenov,a   Alexander V. Aksenov,*a   Oleg N. Nadein,a   Dmitrii A. Aksenov,a   Alexander N. Smirnova  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-activated nitroalkanes are employed in the design of a one-pot cascade transformation involving metal-free and oxidant-free direct ortho-C–H functionalization, followed by Beckman rearrangement and intramolecular cyclocondensation to produce benzoxazoles and benzobisoxazoles directly from easily available phenols.

Graphical abstract: One-pot synthesis of benzoxazoles via the metal-free ortho-C–H functionalization of phenols with nitroalkanes

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Article information

DOI
https://doi.org/10.1039/C5RA15128G
Article type
Paper
Submitted
29 Jul 2015
Accepted
17 Aug 2015
First published
18 Aug 2015

RSC Adv., 2015,5, 71620-71626

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One-pot synthesis of benzoxazoles via the metal-free ortho-C–H functionalization of phenols with nitroalkanes

N. A. Aksenov, A. V. Aksenov, O. N. Nadein, D. A. Aksenov, A. N. Smirnov and M. Rubin, RSC Adv., 2015, 5, 71620 DOI: 10.1039/C5RA15128G

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