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

3- and 5-Furylcyclohexenones were obtained by the Michael reaction of furan chalcones with acetoacetic ester. Intermediate -cycloketols were isolated in many cases. It was found that transformations of -cycloketols by HClO₄ and TrClO₄ were a function of the nature of the substituent in position5 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.Kuban State Technological University, Krasnodar 350072. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 639–647, May, 1996. Original article submitted February 21, 1996.