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

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Contents Vol 59(5)

doi:10.1071/CH05339

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

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

^A RMIT University, School of Applied Sciences, Melbourne VIC 3001, Australia.
^B Corresponding author. Email: trevor.rook@rmit.edu.au





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Australian Journal of Chemistry 59(5) 336–339 http://dx.doi.org/10.1071/CH05339
Submitted: 20 December 2005 Accepted: 24 May 2006 Published online: 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.