Synthesis, Table of Contents Synthesis 2014; 46(08): 1107-1113DOI: 10.1055/s-0033-1340827 paper © Georg Thieme Verlag Stuttgart · New YorkChemoselective Reduction of Functionalized 5-Nitroisoxazoles: Synthesis of 5-Amino- and 5-[Hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles Elena B. Averina* a Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation b IPhaC RAS, Severnyi Proezd, 1, Chernogolovka, Moscow Region, 142432, Russian Federation Fax: +7(495)9393969 Email: elaver@org.chem.msu.ru , Dmitry A. Vasilenko a Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation , Yuri V. Samoilichenko a Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation , Yuri K. Grishin a Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation , Victor B. Rybakov a Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation , Tamara S. Kuznetsova a Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation b IPhaC RAS, Severnyi Proezd, 1, Chernogolovka, Moscow Region, 142432, Russian Federation Fax: +7(495)9393969 Email: elaver@org.chem.msu.ru , Nikolay S. Zefirov a Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation b IPhaC RAS, Severnyi Proezd, 1, Chernogolovka, Moscow Region, 142432, Russian Federation Fax: +7(495)9393969 Email: elaver@org.chem.msu.ru› Author AffiliationsRecommend Article Abstract Buy Article All articles of this category 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 Key words Key wordsreduction - chemoselectivity - isoxazoles - radical reaction - tetrahydrofuran Full Text References References 1a Lang SA, Lin Y.-I In Comprehensive Heterocyclic Chemistry . Vol. 6. Katritzky AR, Rees CW. Pergamon; Oxford: 1984: 1 1b Giomi D, Cordero FM, Machetti F In Comprehensive Heterocyclic Chemistry . Vol. 4. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Oxford: 2008: 365 2a Liu T, Dong X, Xue N, Wu R, He Q, Yang B, Hu Y. Bioorg. Med. Chem. 2009; 17: 6279 2b Salem AM, Mohamed GM, Sulaiman AM, Mohammed NY. Chem. Pharm. 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