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Synthesis 2014; 46(08): 1107-1113
DOI: 10.1055/s-0033-1340827
DOI: 10.1055/s-0033-1340827
paper
Chemoselective Reduction of Functionalized 5-Nitroisoxazoles: Synthesis of 5-Amino- and 5-[Hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles
Further Information
Publication History
Received: 06 December 2013
Accepted after revision: 24 January 2014
Publication Date:
19 February 2014 (online)
Abstract
Reduction by using SnCl2 of easily accessible 5-nitroisoxazoles substituted with an electron-withdrawing group (EWG) has been studied. Whereas the reaction in ethanol yielded 5-aminoisoxazoles, performing the reaction in tetrahydrofuran gave previously unknown 5-[hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles. Both reduction procedures were optimized to afford the corresponding products in good to excellent yields. Some mechanistic details concerning the inclusion of the tetrahydrofuranyl moiety into the reaction product are discussed
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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