2-pyridones from cyanoacetamides and enecarbonyl compounds: application to the synthesis of nothapodytine B.
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).
Carles
Lionel
L
Laboratoire de Synthèse et Méthodologie Organiques (LSMO)-UMR CNRS 5078, Université Claude Bernard Lyon 1, France.
Narkunan
Kesavaram
K
Penlou
Sébastien
S
Rousset
Laurence
L
Bouchu
Denis
D
Ciufolini
Marco A
MA
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*
D000473:Alkanes; D007212:Indolizines; D007659:Ketones; D009570:Nitriles; D011728:Pyridones; D011804:Quinolines; C414097:nothapodytine B; D010100:Oxygen; C031594:2-cyanoacetamide