Furylcyclohexenones. 1. Synthesis and properties of 3- and 5-furyl-6-ethoxycarbonylcyclohexenones

Article abstract of DOI:10.1007/BF01164783

3- and 5-Furylcyclohexenones were obtained by the Michael reaction of furan chalcones with acetoacetic ester. Intermediate β-cycloketols were isolated in many cases. It was found that transformations of β-cycloketols by HClO₄ and TrClO₄ were a function of the nature of the substituent in position 5 of the alicycle. 5-Arylketols undergo dehydration, while 5-furyl derivatives split both water and the furan fragment, resulting in aromatization of the alicycle. The structure of the synthesized compounds was confirmed by the IR and PMR spectra. 1996 Plenum Publishing Corporation.