Chemoselective Reduction of Functionalized 5-Nitroisoxazoles: Synthesis of 5-Amino- and 5-[Hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles

Elena B. Averina; Dmitry A. Vasilenko; Yuri V. Samoilichenko; Yuri K. Grishin; Victor B. Rybakov; Tamara S. Kuznetsova; Nikolay S. Zefirov

doi:10.1055/s-0033-1340827

Synthesis, Table of Contents

Synthesis 2014; 46(08): 1107-1113
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

Authors

Elena B. Averina*

^aLomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation

^bIPhaC RAS, Severnyi Proezd, 1, Chernogolovka, Moscow Region, 142432, Russian Federation Fax: +7(495)9393969 Email: elaver@org.chem.msu.ru
Dmitry A. Vasilenko

^aLomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation
Yuri V. Samoilichenko

^aLomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation
Yuri K. Grishin

^aLomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation
Victor B. Rybakov

^aLomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation
Tamara S. Kuznetsova

^aLomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation

^bIPhaC RAS, Severnyi Proezd, 1, Chernogolovka, Moscow Region, 142432, Russian Federation Fax: +7(495)9393969 Email: elaver@org.chem.msu.ru
Nikolay S. Zefirov

^aLomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russian Federation

^bIPhaC RAS, Severnyi Proezd, 1, Chernogolovka, Moscow Region, 142432, Russian Federation Fax: +7(495)9393969 Email: elaver@org.chem.msu.ru

Abstract

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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

reduction - chemoselectivity - isoxazoles - radical reaction - tetrahydrofuran

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References

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