Base-Induced Cycloaddition of Tosylmethyl or (tert-Butoxycarbonyl)methyl Isocyanide to 1,4-Disubstituted 2,3-Dinitro-1,3-butadienes. Access to 2,3-Disubstituted 4-Ethynylpyrroles (Articolo in rivista)

Type
Label
  • Base-Induced Cycloaddition of Tosylmethyl or (tert-Butoxycarbonyl)methyl Isocyanide to 1,4-Disubstituted 2,3-Dinitro-1,3-butadienes. Access to 2,3-Disubstituted 4-Ethynylpyrroles (Articolo in rivista) (literal)
Anno
  • 1995-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/0040-4020(95) (literal)
Alternative label
  • Dell'Erba C.; Giglio A.; Mugnoli A.; Novi M.; Petrillo G.; Stagnaro P. (1995)
    Base-Induced Cycloaddition of Tosylmethyl or (tert-Butoxycarbonyl)methyl Isocyanide to 1,4-Disubstituted 2,3-Dinitro-1,3-butadienes. Access to 2,3-Disubstituted 4-Ethynylpyrroles
    in Tetrahedron (Oxf., Print); PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD (Regno Unito)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Dell'Erba C.; Giglio A.; Mugnoli A.; Novi M.; Petrillo G.; Stagnaro P. (literal)
Pagina inizio
  • 5181 (literal)
Pagina fine
  • 5192 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://ac.els-cdn.com/004040209598713R/1-s2.0-004040209598713R-main.pdf?_tid=6ea57dba-0010-11e3-bdab-00000aab0f27&acdnat=1375955812_2f55c8cd50ca579c6eefa5c84acaff43 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 51 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
  • Scopu (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dell'Erba C.; Giglio A.; Mugnoli A.; Novi M.; Petrillo G. Universit√† di Genova Stagnaro P. Universit√† di Genova (attualmente CNR-ISMAC Genova) (literal)
Titolo
  • Base-Induced Cycloaddition of Tosylmethyl or (tert-Butoxycarbonyl)methyl Isocyanide to 1,4-Disubstituted 2,3-Dinitro-1,3-butadienes. Access to 2,3-Disubstituted 4-Ethynylpyrroles (literal)
Abstract
  • The reactions of 1,4-disubstituted 23-dinitro-1,3-butadienes 1a-g in THF with isocyanides XCH(2)NC (TosMIC, X = tosyl; TBICA, X = COOBu(t)) and DBU furnish good to moderate yields of 2,3-disubstituted 4- ethynylpyrroles 5a-g or 6a-g. In the reaction of Ig with TosMIC and DBU the nitrovinyl pyrrole 7g and the 3,3'-dipyrrole 4g are also isolated as by-products. A mechanism involving sequential base-induced addition, elimination and cyclization steps is advanced to account for the formation of the isolated products. (literal)
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