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Thieme Gruppe, Synthesis: Journal of Synthetic Organic Chemistry, 03(51), p. 747-756, 2018

DOI: 10.1055/s-0037-1611056

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N-Oxide-Controlled Chemoselective Reduction of Nitrofuroxans

Journal article published in 2018 by Leonid L. Fershtat ORCID, Dmitry M. Bystrov ORCID, Egor S. Zhilin, Nina N. Makhova
Distributing this paper is prohibited by the publisher
Distributing this paper is prohibited by the publisher

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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.