Issue 23, 2009

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
18 Jun 2009
Accepted
03 Sep 2009
First published
01 Oct 2009

Org. Biomol. Chem., 2009,7, 4936-4942

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

H. McNab, M. Morrow, S. Parsons, D. A. Shannon and K. Withell, Org. Biomol. Chem., 2009, 7, 4936 DOI: 10.1039/B911951E

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