Synthetic Exploitation of the Ring-Opening of 3,4-Dinitrothiophene. Part 4. Synthesis of 1,4-Disubstituted 3-Hydroxyimino-2-nitro-1-butenes and their Cyclization to 4-Nitroisoxazoles (Articolo in rivista)

Type
Label
  • Synthetic Exploitation of the Ring-Opening of 3,4-Dinitrothiophene. Part 4. Synthesis of 1,4-Disubstituted 3-Hydroxyimino-2-nitro-1-butenes and their Cyclization to 4-Nitroisoxazoles (Articolo in rivista) (literal)
Anno
  • 1994-01-01T00:00:00+01:00 (literal)
Alternative label
  • Dell'Erba C.; Novi M.; Petrillo G.; Stagnaro P. (1994)
    Synthetic Exploitation of the Ring-Opening of 3,4-Dinitrothiophene. Part 4. Synthesis of 1,4-Disubstituted 3-Hydroxyimino-2-nitro-1-butenes and their Cyclization to 4-Nitroisoxazoles
    in Journal of heterocyclic chemistry; WILEY-BLACKWELL, 111 RIVER ST, HOBOKEN 07030-5774, NJ (Stati Uniti d'America)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Dell'Erba C.; Novi M.; Petrillo G.; Stagnaro P. (literal)
Pagina inizio
  • 861 (literal)
Pagina fine
  • 865 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://onlinelibrary.wiley.com/doi/10.1002/jhet.5570310429/pdf (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 31 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dell'Erba C.; Novi M.; Petrillo G. Università di Genova Stagnaro P. Università di Genova (attualmente CNR-ISMAC Genova) (literal)
Titolo
  • Synthetic Exploitation of the Ring-Opening of 3,4-Dinitrothiophene. Part 4. Synthesis of 1,4-Disubstituted 3-Hydroxyimino-2-nitro-1-butenes and their Cyclization to 4-Nitroisoxazoles (literal)
Abstract
  • The reduction of a single nitrovinyl moiety in 1,4-dialkyl- and 1,4-diaryl-2,3-dinitro-1,3-butadienes 1 with stannous chloride dihydrate in ethyl acetate furnishes the corresponding 3-hydroximino-2-nitro-1-butenes 4 in satisfactory yields. The oxidative cyclization of the latter compounds gives variable yields of 3,5-disubstituted 4-nitroisoxazoles 5, most likely arising from aromatization of the corresponding 4,5-dihydroisoxazoles, formed through an intramolecular Michael addition of the hydroximino group in 4 to the nitroalkene functionality. In the case of the 1-naphthyl derivative 4d such oxidative cyclization mainly leads to the competitive formation of 3-[(1-naphthyl)methyl]-2-nitrobenzo[f]quinoline N-oxide 7. (literal)
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