Reduction of enaminones in the preparation of 3-aminocyclohexanols; a novel preparation of tetronic acid
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 588-591
- https://doi.org/10.1039/p19750000588
Abstract
Reduction of enaminones derived from cyclohexane-1,3-dione gives the corresponding 3-aminocyclohexanols. In the case of the N-unsubstituted derivative the major product is the trans-isomer. The position of attack of ammonia on 2-acetylcyclopentanone and 2-acetylcyclohexanone has been elucidated by reduction of the derived enaminones. In the former case the base attacks the side-chain carbonyl group, but in the latter the ring carbonyl group. Reduction of 2-(substituted amino)fumaric esters gave enaminone analogues of tetronic acid, hydrolysis of which afforded tetronic acid [4-hydroxyfuran-2(5H)-one] itself.Keywords
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