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

Raju Adhikari; Dionne A. Jones; Andris J. Liepa; Roland H. Nearn

doi:10.1071/CH05286

RESEARCH ARTICLE

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

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

+ Author Affiliations

- Author Affiliations

^A CSIRO Molecular and Health Technologies, Clayton South VIC 3169, Australia.

^B Corresponding author. Email: andy.liepa@csiro.au

Australian Journal of Chemistry 58(12) 882-890 https://doi.org/10.1071/CH05286
Submitted: 14 October 2005 Accepted: 22 November 2005 Published: 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.

Acknowledgments

We thank E. I. DuPont de Nemours and Co., Agricultural Products Department, for biological screening of these compounds.

References

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

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

Abstract

Acknowledgments

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