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The nature of the alkyl group in the ester moieties of dimethyl and di-tert-butyl 2-aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylates affects the direction of their reactions with difunctional nucleophiles. The dimethyl esters react with hydrazine hydrate to give the corresponding tetrahydroindazoles, while their tert-butyl analogs are converted under similar conditions into 6-hydrazones. Reactions of both dimethyl and di-tert-butyl 6-oxocyclohexane-1,3-dicarboxylates with hydroxylamine lead to formation of 6-hydroxyimino derivatives.

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“…The physical constants, spectral parameters, and procedures for preparation of compounds Ia3Ih were reported previously [6,7].…”

Section: Methodsmentioning

confidence: 99%

Reactions of dimethyl and di-tert-butyl 2-aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylates with difunctional nucleophiles

et al. 2004

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“…The antimicrobial activity of the synthesized compounds has been evaluated.It was established previously that b-cycloketols and their derivatives exhibit antimicrobial and anti-inflammatory activity [1,2]. It seemed interesting to study the reaction of dialkyl 2-aryl-6-hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxylates with tosylhydrazine in order to synthesize new biologically active compounds.…”

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confidence: 99%

Synthesis and antimicrobial activity of dialkyl-2-aryl-6-hydroxy-6-methyl-4-( p-toluenesulfonylaminoimino) cyclohexane-1,3-dicarboxylates

et al. 2010

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Reaction of dialkyl-2-aryl-6-hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxylates with tosylhydrazide proceeds via the alicyclic carbonyl group to give dialkyl-2-aryl-6-hydroxy-6-methyl-4-(p-toluenesulfonylaminoimino)cyclohexane-1,3-dicarboxylates. The antimicrobial activity of the synthesized compounds has been evaluated.It was established previously that b-cycloketols and their derivatives exhibit antimicrobial and anti-inflammatory activity [1,2]. It seemed interesting to study the reaction of dialkyl 2-aryl-6-hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxylates with tosylhydrazine in order to synthesize new biologically active compounds.Diacetyl-substituted cycloketols are known to react with hydrazine to form the corresponding indazoles [3]. The reaction of dialkyl 2-aryl-6-hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxylates (Ia -m) with tosylhydrazide with heating in EtOH produced dialkyl 2-aryl-6-hydroxy-6-methyl-4-(p-toluenesulfonylaminoimino)cyclohexane-1,3-dicarboxylates (IIa -m) ( Table 1). R = OCH 3 (Ia, b; IIa, b); OCH(CH 3 ) 2 (Ic, IIc); OC 2 H 5 (Id -i, IId -i);

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“…Previously, we reported [2] on the antimicrobial activity of 3-aryl-5-hydroxy-5-methyl-2,4-di(methoxycarbonyl)cyclohexanones synthesized using this reaction.…”

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Synthesis and Antimicrobial Activity of 2,4-Dibenzyloxy(Diallyloxy)carbonyl-3-aryl-5-hydroxy-5-methylcyclohexanones

et al. 2005

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A series of 2,4-dibenzyloxy(diallyloxy)carbonyl-3-aryl-5-hydroxy-5-methylcyclohexanones have been obtained via reactions of benzylacetoacetate and allylacetoacetate with aromatic aldehydes in the presence of a basic catalyst (piperidine). The proposed structures are confirmed by the results of 1 H NMR spectroscopy, IR absorption spectroscopy, and high-resolution mass spectrometry measurements. Data on the antimicrobial activity of the synthesized compounds are presented.

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Cited by 23 publications

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Reactions of dimethyl and di-tert-butyl 2-aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylates with difunctional nucleophiles

Reactions of dimethyl and di-tert-butyl 2-aryl-4-hydroxy-4-methyl-6-oxocyclohexane-1,3-dicarboxylates with difunctional nucleophiles

Synthesis and antimicrobial activity of dialkyl-2-aryl-6-hydroxy-6-methyl-4-( p-toluenesulfonylaminoimino) cyclohexane-1,3-dicarboxylates

Synthesis and Antimicrobial Activity of 2,4-Dibenzyloxy(Diallyloxy)carbonyl-3-aryl-5-hydroxy-5-methylcyclohexanones

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