Synthesis, Table of Contents Synthesis 2019; 51(03): 747-756DOI: 10.1055/s-0037-1611056 paper © Georg Thieme Verlag Stuttgart · New York N-Oxide-Controlled Chemoselective Reduction of Nitrofuroxans Authors Author Affiliations Leonid L. Fershtat * a N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation Email: fershtat@bk.ru Dmitry M. Bystrov a N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation Email: fershtat@bk.ru b Department of Chemistry, Moscow State University, 119991 Moscow, Leninskie Gory 1-3, Russian Federation Egor S. Zhilin a N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation Email: fershtat@bk.ru b Department of Chemistry, Moscow State University, 119991 Moscow, Leninskie Gory 1-3, Russian Federation Nina N. Makhova a N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation Email: fershtat@bk.ru Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract A facile and chemoselective SnCl2-mediated mild reduction of regioisomeric 3- and 4-nitrofuroxans for the synthesis of aminofurazans and aminofuroxans in good yields is developed. Reduction of 4-nitrofuroxans results in the selective formation of 4-aminofuroxans, while analogous reduction of 3-nitrofuroxans affords 3-aminofurazans as a result of simultaneous reduction of the nitro group and exocyclic N–O bond. Key words Key wordsfuroxans - furazans - reduction - heterocycles - chemoselectivity Full Text References References 1a Paton RM. 1,2,5-Oxadiazoles . In Comprehensive Heterocyclic Chemistry II . Vol. 4. Katritzky AR. Rees CW. Scriven EF. V. Pergamon; Oxford: 1996: 229-266 1b Nikonov GN. Bobrov S. 1,2,5-Oxadiazoles . 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Mass Spectrom. 2014; 20: 233 Supplementary Material Supplementary Material Supporting Information (PDF) (opens in new window)
