Synthesis of N-Substituted γ-Methylene γ-Lactams

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Contents Vol 58(12)

doi:10.1071/CH05286

Synthesis of N-Substituted γ-Methylene γ-Lactams*

Raju Adhikari ^A, Dionne A. Jones ^A, Andris J. Liepa ^A ^B, Roland H. Nearn ^A

^A CSIRO Molecular and Health Technologies, Clayton South VIC 3169, Australia.
^B Corresponding author. Email: andy.liepa@csiro.au





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Australian Journal of Chemistry 58(12) 882–890 http://dx.doi.org/10.1071/CH05286
Submitted: 14 October 2005 Accepted: 22 November 2005 Published online: 20 December 2005

Abstract

N-Substituted cyanoacetamides 1 were condensed with 1,2-diketones 2 under base catalysis to form γ-hydroxy γ-lactams 3. Treatment of 3 with acids gave novel fungicidal γ-methylene γ-lactams 4. The exocyclic double bond of 4b reacted reversibly with 4-toluene sulfinate.

^* Dedicated to the memory of Dr Dionne Anne Jones.