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Communication | Regular issue | Vol 41, No. 9, 1995, pp.1915-1922
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7147
Synthesis of 5-Phosphonyl-2(1H)-pyridones from Primary β-Enaminophosphonate and Acetylenic Esters

Francisco Palacios, Jesús García, Ana Ma Ochoa de Retana, and Julen Oyarzabal

*Departamento de Química Orgánica, Facultad de Farmacia, Universidad del País Vasco, Apto. 450, 01080 Vitoria, Spain


Primary β-enaminophosphonates (2) are obtained from metallated diethyl methylphosphonate and nitriles. Reaction of enamines (2) with ethyl propiolate and dimethyl acetylenedicarboxylate yields 1:1 adducts (7) and (8), respectively. Treatment of monoadducts (7) with sodium hydride leads to 5-phosphonyl-2(1H)-pyridones (1). Functionalized enamines (8) undergo thermal cyclocondensation to give pyridones (9).