title: Domino reactions of diazodicarbonyl compounds with α,β-unsaturated δ-amino esters: a convenient way towards 2-oxopiperidines, dihydropyridinones and isoquinolinediones.
abstract: Thermal decomposition of a series of diazodicarbonyl compounds in the presence of α,β-unsaturated δ-amino esters and sodium hydride gives rise to a variety of nitrogenous heterocycles. The direction of these processes is highly dependent on the structure of the initial reagents giving rise to the formation of multi-functionalized 2-oxopiperidines, 5,6-dihydropyridin-2(1H)-ones or tetrahydroisoquinoline-1,6(2H,8aH)-diones. The reactions occur in domino processes involving the Wolff rearrangement of diazocarbonyl compounds, NaH-catalyzed anti-stereoselective intramolecular Michael addition to the α,β-unsaturated system of amino esters, and in some cases also cycloelimination and intramolecular Claisen condensation of the initial products formed.
authors.affiliation: Saint-Petersburg State University, University Prosp. 26, St.-Petersburg 198504, Russia. vnikola@VN6646.spb.edu.
authors.forename: J J
authors.initials: JJ
authors.lastname: Medvedev
authors.forename: M V
authors.initials: MV
authors.lastname: Meleshina
authors.forename: T L
authors.initials: TL
authors.lastname: Panikorovskii
authors.forename: C
authors.initials: C
authors.lastname: Schneider
authors.forename: V A
authors.initials: VA
authors.lastname: Nikolaev