Issue 31, 2016
From the journal:

RSC Advances

A base promoted multigram synthesis of aminoisoxazoles: valuable building blocks for drug discovery and peptidomimetics†

Bohdan A. Chalyk,a   Inna Y. Kandaurova,b   Kateryna V. Hrebeniuk,b   Olga V. Manoilenko,a   Irene B. Kulik,d   Rustam T. Iminov,a   Vladimir Kubyshkin,e   Anton V. Tverdokhlebov,*a   Osman K. Ablialimov*a  and  Pavel K. Mykhailiuk*ac  

* Corresponding authors

a Enamine Ltd., Chervonotkatska 78, 01103 Kyiv, Ukraine
E-mail: A.tverdohlebov@mail.enamine.net, O.ablialimov@mail.enamine.net, Pavel.Mykhailiuk@gmail.com, Pavel.Mykhailiuk@mail.enamine.net
Web: http://www.enamine.net

b Department of Chemistry, Kyiv Polytechnic Institute, Prosp. Peremohy 37, Kyiv 03056, Ukraine

c Department of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska Street 64, Kyiv 01601, Ukraine

d Institute of Bioorganic Chemistry & Petrochemistry, NAS of Ukraine, Murmanska 1, Kyiv 02660, Ukraine

e Institute of Chemistry, Technical University of Berlin, Müller-Breslau-Str. 10, Berlin 10623, Germany

Abstract

A practical multigram metal free synthesis of isoxazole-containing building blocks from commercially available amino acids was elaborated. The key reaction was a regioselective [3 + 2]-cycloaddition of in situ generated nitrile oxides with alkynes/enamines. The obtained building blocks were used in the preparation of bioactive compounds and peptidomimetics.

Graphical abstract: A base promoted multigram synthesis of aminoisoxazoles: valuable building blocks for drug discovery and peptidomimetics

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Article information

DOI
https://doi.org/10.1039/C6RA02365G
Article type
Paper
Submitted
26 Jan 2016
Accepted
23 Feb 2016
First published
01 Mar 2016
This article is Open Access
Creative Commons BY license

RSC Adv., 2016,6, 25713-25723

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A base promoted multigram synthesis of aminoisoxazoles: valuable building blocks for drug discovery and peptidomimetics

B. A. Chalyk, I. Y. Kandaurova, K. V. Hrebeniuk, O. V. Manoilenko, I. B. Kulik, R. T. Iminov, V. Kubyshkin, A. V. Tverdokhlebov, O. K. Ablialimov and P. K. Mykhailiuk, RSC Adv., 2016, 6, 25713 DOI: 10.1039/C6RA02365G

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