title: 2-pyridones from cyanoacetamides and enecarbonyl compounds: application to the synthesis of nothapodytine B.
abstract: The condensation of an enone or enal with cyanoacetamide derivatives and t-BuOK furnishes either 3-cyano-2-pyridones or 3-unsubstituted-2-pyridones, depending on whether the reaction is carried out in the presence or in the absence of O(2). In the first case, in situ oxidation of Michael-type intermediates takes place; in the second case, the products result from "decyanidative aromatization" of such intermediates. A one-step synthesis of 3-alkyl-2-pyridones has been devised on the basis of decyanative union of an enone/enal and a 2-alkylcyanoacetamide. The new reaction forms the centerpiece of an unusually concise synthesis of nothapodytine B (mappicine ketone).
authors.affiliation: Laboratoire de Synthèse et Méthodologie Organiques (LSMO)-UMR CNRS 5078, Université Claude Bernard Lyon 1, France.
authors.forename: Lionel
authors.initials: L
authors.lastname: Carles
authors.forename: Kesavaram
authors.initials: K
authors.lastname: Narkunan
authors.forename: Sébastien
authors.initials: S
authors.lastname: Penlou
authors.forename: Laurence
authors.initials: L
authors.lastname: Rousset
authors.forename: Denis
authors.initials: D
authors.lastname: Bouchu
authors.forename: Marco A
authors.initials: MA
authors.lastname: Ciufolini
mesh_terms: D000473:Alkanes / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000295:instrumentation* / Q000379:methods*; D007212:Indolizines / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D011728:Pyridones / Q000138:chemical synthesis*; D011804:Quinolines / Q000138:chemical synthesis*
chemical_list: D000473:Alkanes; D007212:Indolizines; D007659:Ketones; D009570:Nitriles; D011728:Pyridones; D011804:Quinolines; C414097:nothapodytine B; D010100:Oxygen; C031594:2-cyanoacetamide