Regioselective Ethanolamination and Ketalization of 3-Ph-2,4-diacetyl(diethoxycarbonyl)-5-hydroxy-5-methylcyclohexanones

Abstract

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.

Syntheses and some features of five new cyclohexane-1,3-dicarboxylates with multiple stereogenic centers

“…by condensation of acetylacetone or acetoacetic acid esters with aldehydes. These compounds are known for their important biological activities such as herbicidal, antibacterial, antifungal, convulsant, anticonvulsant, antiimplantation and antiasthmone, besides being useful in organic synthesis and in industry [5][6][7][8][9]. Thus, they are useful synthons in further synthetic endeavours, as they have multiple keto, hydroxy and ester functionalities, potentially available for further transformations.…”

“…The methods of further modification of the thus prepared cyclohexanones with mono-or polyfunctional nucleophiles are also well studied [20][21][22][23][24][25][26][27][28]. For instance, it was found that reactions of hydroxylamine [9], hydrazine [23,24], ethylenediamine [27], ethanolamine [8,26,27], ethylene glycol [4], substituted aromatic amines [20,21,25], tosylhydrazide [22] and benzidine [28] with diethyl-4-hydroxy-4-methyl-6-oxo-2-phenylcyclohexane-1,3-dicarboxylate give isoxazole, imidazole and 1,3-dioxolane rings, Schiff base condensation products, etc. Moreover, in some cases the cyclization processes depend on temperature, i.e.…”

“…As was mentioned, usually synthesis of the cyclohexanones of this type is carried out via one-pot MCRs, where several organic fragments are coupled in one step with a carbon-carbon formation and subsequent cyclization [5][6][7][8][10][11][12][13][14][15][16][17][18][19]. The methods of further modification of the thus prepared cyclohexanones with mono-or polyfunctional nucleophiles are also well studied [20][21][22][23][24][25][26][27][28].…”

Evaluation of anti-fungal properties of new functionally substituted cyclohexanone compounds

“…Diethyl-1-isobutyl-9-hydroxy-9-methyl-7-phenyl-1,4-diazaspiro [4.5]decane-6,8dicarboxylate (compound I) synthesized as described by Magerramov et al, 2013 [4] and 2,4-Diacetyl-5-hydroxy-5-methyl-3-phenyl-N-oxyethyl-1-cyclohexenylamine (compound II) synthesized as described by Kriven'ko et al, 2003 [5] [4][5] Standard agar well diffusion method [6] was used to determine antifungal properties of test compounds at three different concentrations i.e. 0.3%, 0.1% and 0.05%.…”

Crystal Structure of Diethyl-5-(2-(1-(4-Bromophenyl)ethylidene)hydrazinyl)-3-Methyl-1,2-Dihydro-[1,1'-Diphenyl]-2,6-Dicarboxylate

“…Ⱦɢɚɥɤɨɤɫɢɡɚɦɟɳɟɧɧɵɟ E-ɤɟɬɨɥɵ ɰɢɤɥɨɝɟɤɫɚɧɨɜɨɝɨ ɪɹɞɚ ɡɚ ɫɱɟɬ ɩɨɥɢɮɭɧɤɰɢɨɧɚɥɶɧɨɫɬɢ ɢ ɨɫɨɛɟɧɧɨ ɛɥɚɝɨɩɪɢɹɬɧɨɝɨ ɪɚɫɩɨɥɨɠɟɧɢɹ ɤɚɪɛɨɧɢɥɶɧɵɯ ɝɪɭɩɩ ɩɪɟɞɨɫɬɚɜɥɹɸɬ ɛɨɝɚɬɵɟ ɫɢɧɬɟɬɢɱɟɫɤɢɟ ɜɨɡɦɨɠɧɨɫɬɢ ɞɥɹ ɤɨɧɫɬɪɭɢɪɨɜɚɧɢɹ ɧɚ ɢɯ ɨɫɧɨɜɟ ɲɢɪɨɤɨɝɨ ɤɪɭɝɚ ɩɪɨɢɡɜɨɞɧɵɯ ɦɨɧɨɢ ɛɢɰɢɤɥɢɱɟɫɤɨɝɨ ɫɬɪɨɟɧɢɹ ɫ ɪɚɡɥɢɱɧɵɦ ɬɢɩɨɦ ɝɟɬɟɪɨɚɬɨɦɨɜ [1][2][3][4][5][6][7][8]. ȼ ɥɢɬɟɪɚɬɭɪɟ ɩɪɟɜɪɚɳɟɧɢɹ ɩɪɨɞɭɤɬɨɜ ɞɟɝɢɞɪɚɬɚɰɢɢ ɷɬɢɯ E-ɤɟɬɨɥɨɜ -ɞɢɚɥɤɨɤɫɢɡɚɦɟɳɟɧɧɵɯ ɰɢɤɥɨɝɟɤɫɟɧɨɧɨɜ ɧɟ ɢɫɫɥɟɞɨɜɚɥɢɫɶ, ɚ ɦɟɠɞɭ ɬɟɦ ɧɚɥɢɱɢɟ ɧɟɩɪɟɞɟɥɶɧɨɝɨ ɤɟɬɨɧɧɨɝɨ ɮɪɚɝɦɟɧɬɚ ɜ ɫɨɫɬɚɜɟ ɷɬɢɯ ɫɨɟɞɢɧɟɧɢɣ ɜ ɪɟɚɤɰɢɹɯ ɫ ɚɦɢɧɧɵɦɢ ɧɭɤɥɟɨɮɢɥɚɦɢ ɦɨɝɭɬ ɜɵɡɜɚɬɶ ɨɛɪɚɡɨɜɚɧɢɟ ɩɪɨɞɭɤɬɨɜ ɤɚɤ ɩɪɢɫɨɟɞɢɧɟɧɢɹ ɩɨ ɤɪɚɬɧɨɣ ɫɜɹɡɢ ɋ=ɋ, ɬɚɤ ɢ ɤɨɧɞɟɧɫɚɰɢɢ ɩɨ ɤɚɪɛɨɧɢɥɶɧɨɣ ɝɪɭɩɩɟ ɚɥɢɰɢɤɥɚ.…”