Diels–Alder Reactions of 3-Furylamines in Organic and Aqueous Solvents

Anthony R. Lingham; Helmut M. Hügel; Trevor J. Rook

doi:10.1071/CH05339

RESEARCH ARTICLE

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Diels–Alder Reactions of 3-Furylamines in Organic and Aqueous Solvents

Anthony R. Lingham ^A , Helmut M. Hügel ^A and Trevor J. Rook ^A ^B

+ Author Affiliations

- Author Affiliations

^A RMIT University, School of Applied Sciences, Melbourne VIC 3001, Australia.

^B Corresponding author. Email: trevor.rook@rmit.edu.au

Australian Journal of Chemistry 59(5) 336-339 https://doi.org/10.1071/CH05339
Submitted: 20 December 2005 Accepted: 24 May 2006 Published: 13 June 2006

Abstract

Various 5-methyl-3-aminofurans have been shown to undergo facile Diels–Alder reactions with methyl acrylate in aqueous media. Reactions proceeded with exclusive regiochemistry, and enamine cycloadducts were readily hydrolyzed to afford 7-oxabicyclo[2.2.1]heptanones in high yields.

Acknowledgments

Financial support from the School of Applied Science, RMIT University, is acknowledged. We thank Dr Julie Niere, Dr Peter McKay, and Dr Gary Amiet for their advice on synthetic problems and NMR interpretation, and Britta Drevermann for assistance with manuscript revisions. We also thank Dr Jonathan White (University of Melbourne) for X-ray crystal structure data and Sally Duck (Monash University) for high-resolution mass spectrometry analysis.

References

Diels–Alder Reactions of 3-Furylamines in Organic and Aqueous Solvents

Abstract

Acknowledgments

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