title: Exploiting the divergent reactivity of α-isocyanoacetate: multicomponent synthesis of 5-alkoxyoxazoles and related heterocycles.
abstract: A novel multicomponent synthesis of 5-alkoxyoxazoles, based on a new reactivity profile of α-isocyanoacetates, is described. Thus, simply heating a solution of amine, aldehyde, and α-(EWG-phenyl)-α-isocyanoacetate or α-(4-pyridyl)-α-isocyanoacetate (EWG=electron-withdrawing group) in toluene provided 5-alkoxyoxazoles in good to excellent yields. Reaction of the 5-alkoxyoxazoles with various α,β-unsaturated acyl chlorides led to the formation of epoxytetrahydropyrrolo[3,4-b]pyridin-5-ones by a domino N-acylation/Diels-Alder cycloaddition sequence. Subsequent fragmentation under basic conditions provided 6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones. A four-component synthesis of the pyridin-5-one compounds, without isolation of the 5-alkoxyoxazole, was subsequently developed.
authors.affiliation: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.
authors.forename: Claudia
authors.initials: C
authors.lastname: Lalli
authors.forename: Marinus J
authors.initials: MJ
authors.lastname: Bouma
authors.forename: Damien
authors.initials: D
authors.lastname: Bonne
authors.forename: Géraldine
authors.initials: G
authors.lastname: Masson
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D017953:Isocyanates / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis*; D010648:Phenylacetates / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D006571:Heterocyclic Compounds; D017953:Isocyanates; D010080:Oxazoles; D010648:Phenylacetates