The reaction of 3-phenyl-2,4-diacetyl(diethoxycarbonyl)-5-hydroxy-5-methyl-cyclohexanones with ethanolamine and ethylene glycol proceeds regioselectively using the carbonyl group of the alicycle to produce the corresponding cyclohexenylethanolamines and dioxolanes.
2001 amines amines (benzene compounds) Q 0120 16 -105 Synthesis of Substituted Cyclohexenyl-, Cyclohexadienylarylamines. -The preparation of title compounds (III) and (IV) is achieved by acid-catalyzed amination of cyclohexanones (I). -(SOROKIN, V. V.; GRIGOR'EV, A V.; RAMAZANOV, A. K.; KRIVEN'KO, A. P.; Russ.
It was discovered that functionally substituted tetrahydroindazoles can be aromatized by the action of sulfur. Previously unknown 3-1~-4-RI-5-acetyl(ethoxycarbonyl)-6-methylindazoles were obtained. The products from aromatization cannot be obtained if a nitro group is introduced or one heteroatom in the substrate is replaced by oxygen.Pyrazoles and isoxazoles have a wide spectrum of biological activity [1]. Condensed pyrazoles and isoxazoles and particularly the polysubstituted compounds have been investigated less in this respect [2]. We have presented the results [3] of investigations into the synthesis and biological activity of cyclohexa(b)pyrazoles and cyclohexa(b)isoxazoles.The aim of the present work was to synthesize benzannelated pyrazoles and isoxazoles by the 2 1 aromatization of 3-R-4-R-5-acetyl(ethoxycarbonyl)-6-hydroxy-6-methyl-2H-4,5,6,7-tetrahydroindazoles Ia-e and their O-hetero analogs IIa, b. Here it seemed of interest to determine the effect of the nature of the substituting groups and of the heteroatom in the substrate on the course of the reaction. The initial tetrahydroindazoles Ia-e and condensed isoxazoles IIa, b were obtained with high yields by our previously developed methods [3] from hydrazine or the readily obtainable hydroxylamine and [3-cyeloketols l/Ia-e, i.e., the products from the condensation of acetylacetone (acetoacetic ester) with aldehydes. All the compounds I and I] except Ic had been obtained and characterized before [3, 4].Compounds Ia-e were aromatized by the action of sulfur at 200~ until the release of hydrogen sulfide had stopped, which required -60 min. Under the selected conditions these tetrahydroindazoles underwent dehydration and dehydrogenation with the formation of previously unknown 3-R2-4-R~-5-acetyl(ethoxycarbonyl)-6 -methylindazoles IVa-d.
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