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Studies on pyrrolidinones. Synthesis of new α-pyridones derivatives

✍ Scribed by Natacha Malecki; Raymond Houssin; Jean-Pierre Héanichart; Daniel Couturier; Ferdinand Petra; Laurent Legentil; Benoîct Rigo

Publisher
Journal of Heterocyclic Chemistry
Year
2003
Tongue
English
Weight
75 KB
Volume
40
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Dimethyl 7‐methoxycarbonylmethyl‐5‐oxo‐1,2,3,5‐tetrahydro‐indolizine‐3,8‐dicarboxylate 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).

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