regioselective ethanolamination and ketalization of 3-ph-2,4-diacetyl(diethoxycarbonyl)-5-hydroxy-5-methylcyclohexanones特定选择的ethanolamination ketalization 3-ph-2,4-diacetyl 5-hydroxy-5-methylcyclohexanones(diethoxycarbonyl).pdfVIP

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regioselective ethanolamination and ketalization of 3-ph-2,4-diacetyl(diethoxycarbonyl)-5-hydroxy-5-methylcyclohexanones特定选择的ethanolamination ketalization 3-ph-2,4-diacetyl 5-hydroxy-5-methylcyclohexanones(diethoxycarbonyl).pdf

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regioselective ethanolamination and ketalization of 3-ph-2,4-diacetyl(diethoxycarbonyl)-5-hydroxy-5-methylcyclohexanones特定选择的ethanolamination ketalization 3-ph-2,4-diacetyl 5-hydroxy-5-methylcyclohexanones(diethoxycarbonyl)

Molecules 2003, 8, 251-255 molecules ISSN 1420-3049 Regioselective Ethanolamination and Ketalization of 3-Ph-2,4- diacetyl(diethoxycarbonyl)-5-hydroxy-5-methylcyclohexanones Adele P. Krivenko, Eleanor A. Kozlova, Alexander V. Grigorev and Vitaly V. Sorokin* Chair of Organic and Bioorganic Chemistry, Saratov State University, 83 Astrakhanskaya Str., Saratov 410026, Russia Author to whom correspondence should be addressed; E-mail: sorokinvv@info.sgu.ru Received: 16 September 2002; in revised form: 24 January 2003 / Accepted: 26 January 2003 / Published: 28 February 2003 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. Keywords: Cyclohexanones, ethanolamine, ethylene glycol, enaminoketones, heterospirans Introduction β-Cycloketols of the 3-R-2,4-diacetyl(diethoxycarbonyl)-5-hydroxy-5-methylcyclohexanone series are available by condensation of acetylacetone or acetoacetic acid esters with aldehydes. By now their chemistry is well-studied. Lately, some reviews have appeared that summarize the theoretical and applied aspects of this chemistry [1, 2]. However, the reactions of these polycarbonyl compounds with 1,4-binucleophilic reagents (ethanolamine, ethylene glycol), possibly leading to valuable compounds of practical use remain unexplored (similar reactions involving monocarbonyl substances are reported in [3]). Molecules 2003, 8