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Synthesis of fluorinated isoxazoles using SelectfluorTM : preparation and characterization of 4-fluoroisoxazole, 4,4,5-trifluoroisoxazoline and 4,4-difluoro-5-hydroxyisoxazoline systems from one-pot and multi-step processes.

Sato, K. and Sandford, G. and Shimizu, K. and Akiyama, S. and Lancashire, M.J. and Yufit, D.S. and Tarui, A. and Omote, M. and Kumadaki, I. and Harusawa, S. and Ando, A. (2016) 'Synthesis of fluorinated isoxazoles using SelectfluorTM : preparation and characterization of 4-fluoroisoxazole, 4,4,5-trifluoroisoxazoline and 4,4-difluoro-5-hydroxyisoxazoline systems from one-pot and multi-step processes.', Tetrahedron., 72 (13). pp. 1690-1698.

Abstract

3,5-Disubstituted 4-fluoroisoxazole, 4,4,5-trifluoroisoxazoline and 4,4-difluoro-5-hydroxyisoxazoline products were obtained from reaction of the corresponding isoxazoles with SelectfluorTM depending upon the reaction conditions. Although the fluorinations proceeded using conventional heating, microwave (μW) irradiation considerably shortened reaction times and enabled a high yielding one-pot cascade fluorination-cyclization from simple diketone substrates. In addition, a related 4-fluoroisoxazole-3-carboxyamide derivative was synthesized.

Item Type:Article
Keywords:Fluoroheteroaromatic, Selective fluorination, 4-fluoroisoxazole, 4,4,5-trifluoroisoxazoline TRPV1 antagonist.
Full text:(AM) Accepted Manuscript
Available under License - Creative Commons Attribution Non-commercial No Derivatives.
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Status:Peer-reviewed
Publisher Web site:http://dx.doi.org/10.1016/j.tet.2016.02.026
Publisher statement:© 2016 This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
Date accepted:08 February 2016
Date deposited:17 February 2016
Date of first online publication:10 February 2016
Date first made open access:10 February 2017

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