Studies on pyrrolidinones. Synthesis of new alpha-pyridones derivatives

摘要

Dimethyl 7-methoxycarbonylmethyl-5-oxo-1,2,3,5-tetrahydro-indolizine-3,8-dicarboxyl ate was synthesized starting from methyl pyroglutamate. A study was made of the reactions of this highly functionalized pyridone with ethyl iodide, selenium oxide, isoamyl nitrite and formaldehyde. Literature reports that reaction of 4-(1-carbomethoxypropyl)-5-carbomethoxy-1,6-cyclopentano-2-pyridone with formaldehyde lead to a 95% yield of a monolactone (26) precursor of camptothecin. Our experiments resulted in 15% of this monolactone and 40% of a new dilactone (27). [References: 61]