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Organic & biomolecular chemistry

Synthetic routes to pyrrolizine-1,5-dione derivatives by flash vacuum pyrolysis of amidomethylene derivatives of Meldrum's acid.


PMID 19907784

Abstract

Methoxymethylene Meldrum's acid 1 reacts with 5- and 6-membered lactams in refluxing acetonitrile to give the N-substituted products 9-15. If the reactions are continued for extended times, the Meldrum's acid derivatives decompose to provide enamidoesters e.g. 22-24. Flash vacuum pyrolysis of the 5-membered ring products 9-13 provides reasonable yields of the fused pyrrolones 31-35. The constitution of the products is supported by X-ray crystal structures of 10, 12, 19, 32 and 34.

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