title: Exploiting the Electrophilic and Nucleophilic Dual Role of Nitrile Imines: One-Pot, Three-Component Synthesis of Furo[2,3-d]pyridazin-4(5H)-ones.
abstract: An expeditious multicomponent reaction to synthesize tetrasubstituted furo[2,3-d]pyridazin-4(5H)-ones is reported. In brief, hydrazonoyl chlorides react with isocyanoacetamides, in the presence of TEA, to give 1,3-oxazol-2-hydrazones which, without being isolated, can react with dimethylacetylene dicarboxylate to afford furo[2,3-d]pyridazin-4(5H)-ones with an unprecedented level of complexity in a triple domino Diels-Alder/retro-Diels-Alder/lactamization reaction sequence.
authors.affiliation: †Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II", via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Mariateresa
authors.initials: M
authors.lastname: Giustiniano
authors.affiliation: ‡Dipartimento di Scienze del Farmaco, Università degli Studi del Piemonte Orientale "A. Avogadro", Largo Donegani 2, 28100 Novara, Italy.
authors.forename: Valentina
authors.initials: V
authors.lastname: Mercalli
authors.affiliation: †Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II", via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Jussara
authors.initials: J
authors.lastname: Amato
authors.affiliation: †Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II", via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Ettore
authors.initials: E
authors.lastname: Novellino
authors.affiliation: ‡Dipartimento di Scienze del Farmaco, Università degli Studi del Piemonte Orientale "A. Avogadro", Largo Donegani 2, 28100 Novara, Italy.
authors.forename: Gian Cesare
authors.initials: GC
authors.lastname: Tron
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D061565:Cycloaddition Reaction; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D006574:Heterocyclic Compounds, 2-Ring; D006835:Hydrazones; D007097:Imines; D009570:Nitriles; C535220:dimethylacetylene