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Ring-opening and recyclization of 3,4-diacylfuroxans by nitrogen nucleophiles |
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| Authors: | SD ShaposhnikovSV Pirogov SF Mel'nikova IV TselinskyC Näther T GraeningT Traulsen W Friedrichsen |
| Institution: | a St.-Petersburg State Institute of Technology (technical university), St.-Petersburg 198013, Russian Federation b Institute of Inorganic Chemistry, University of Kiel, Kiel D-24118, Germany c Institute of Organic Chemistry,University of Kiel, Kiel D-24118, Germany |
| Abstract: | Interaction of 3,4-diacylfuroxans with hydroxylamine hydrochloride results in the formation of substituted 4,5-bis (hydroximino)-4,5-dihydroisoxazoles, whereas the reaction of 3,4-bis(4-methylfurazanoyl-3)furoxan with hydrazine hydrate in acetic acid affords 3-4,5-bis(hydroximino)-4,5-dihydro-1H-pyrazol-3-yl]-4-methylfurazan. N-Acyl-, N-nitro-, N-alkyl- and N-adamantyl derivatives of the latter compound have been synthesized. X-Ray structure determinations together with density functional theoretical calculations are reported. |
| Keywords: | furoxans isoxazoles pyridazines rearrangement |
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