Synthesis and Structure of Diisopropyl 6-Hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxylates and Their Reactions with Nucleophilic Reagents

Гейн, В. Л.; Nosova, N. V.; Potemkin, K. D.; Алиев, З. Г.; Кривенько, А. П.

doi:10.1007/s11178-005-0287-7

Cited by 14 publications

(3 citation statements)

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“…However, the heterocyclization reactions of β-cycloketols are not well studied. Thus, the literature describes the preparation of isoquinolines 2 [3][4][5][6][7], indazoles 3 [8][9][10], benzo[c]isoxazoles 4 [9,10], [1,2,4]triazolo [3-b]quinazolines 5 [11] and pyrazolo[3-c]isoquinolines 6 [12] (Scheme 1) by reactions of beta-cycloketols with various 1,2-and 1,3-dinucleophilic agents. Despite the large attention paid to reactions of aminoazoles with 1,3-dielectrophilic agents (see reviews [13,14]), only a few examples of reactions involving β-cycloketols were found in the literature.…”

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confidence: 99%

The Reaction of 5-Amino-3-(cyanomethyl)-1H-pyrazol-4-carbonitrile with beta-Cycloketols

Доценко

Semenova

Chigorina

et al. 2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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The Reaction of 5-Amino-3-(cyanomethyl)-1H-pyrazol-4-carbonitrile with beta-Cycloketols

Доценко

Semenova

Chigorina

et al. 2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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“…-индазол-5-карбоксилатов 83. Аналогичное взаимодействие с гидроксиламином приводит к оксимам 84, а с фенилгидразином -к гидразонам 85[30] (схема 31).…”

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The synthesis and reactions of diacethyl(dialkoxycarbonyl) substituted hydroxycyclohexanones / A.I.Ismiyev, A.M.Maherramov, V.A.Sukach, M.V.Vovk

Ismiyev¹,

Maherramov²,

Sukach³

et al. 2016

J. org. pharm. chem.

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Обобщены и систематизированы литературные источники, свидетельствующие о важности диацетил (диалкоксикарбонил)замещенных гидроксициклогексанонов как высокофункциональных карбоциклических соединений, с одной стороны, а также о перспективности исследований в области разработки на их основе методов получения разнообразных гетероциклических систем, с другой. Отмечено, что основным методом синтеза диацетил(диэтоксикарбонил)замещенных циклогексанолонов является дикетонная конденсация ацетилацетона или ацетоуксусного эфира с альдегидами при наличии каталитических количеств пиперидина. Важным положительным моментом такого подхода является вариабельность исходных реагентов, что позволяет в широких пределах видоизменять состав заместителей. Вместе с тем, зависимость регионаправленности и селективности реакции от множества факторов делает исследования в этом направлении интересными и не всегда предсказуемыми. Кроме того, обсуждено явление кето-енольной таутомерии диацетилзамещенных циклогексанолонов и определены факторы, контролирующие устойчивость их енольной формы. Сделан вывод о том, что реакции указанных поликарбонильных соединений с амбидентными азотсодержащими нуклеофильными реагентами являются эффективным вариантом синтеза новых представителей биоперспективных карбоаннелированных гетероциклов: изоксазолов, пиразолов, триазоло[3,4-b]хиназолинов, тиено [2,3-c]изохинолинов и пиразоло [3,4-c]изохинолинов. Подчеркнута значимость для органического синтеза процессов окисления, дегидратации и ароматизации гидроксициклогексанонов. THE SYNTHESIS AND REACTIONS OF DIACETHYL(DIALKOXYCARBONYL) SUBSTITUTED HYDROXYCYCLOHEXANONES A.I.Ismiyev, A.M.Maherramov, V.A.Sukach, M.V.VovkThe literature sources concerning the importance of diacetyl (dialkoxycarbonyl) substituted hydroxycyclohexanones as highly functionalized carbocyclic compounds, on the one hand, as well as, on the other hand, the research prospects in the field of synthetic methods development based on these compounds for obtaining various heterocyclic systems have been generalized and systematized. It has been noted that the main method of the synthesis for diacetyl (diethoxycarbonyl) cyclohexanolones is diketone condensation of acetylacetone or ethyl acetoacetate with aldehydes in the presence of catalytic amounts of piperidine. An important useful peculiarity of this approach is a variation of the initial reagents, allowing modification of the substituents in a wide range. However, the dependence of selectivity and regiodirection of the reaction on various factors makes the studies in this area quite interesting and not always predictable. The phenomenon of keto-enol tautomerism of diacetyl substituted cyclohexanolones and factors that control stability of their enol form have been discussed. It has been concluded that reactions of these multicarbonyl compounds with ambident nitrogen-containing nucleophilic reagents are efficacious for the synthesis of new biologically promising The importance of oxidation, dehydration and aromatization processes of hydroxycyclohexanones ...

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“…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).…”

mentioning

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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Synthesis and Structure of Diisopropyl 6-Hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxylates and Their Reactions with Nucleophilic Reagents

Cited by 14 publications

References 6 publications

The Reaction of 5-Amino-3-(cyanomethyl)-1H-pyrazol-4-carbonitrile with beta-Cycloketols

The Reaction of 5-Amino-3-(cyanomethyl)-1H-pyrazol-4-carbonitrile with beta-Cycloketols

The synthesis and reactions of diacethyl(dialkoxycarbonyl) substituted hydroxycyclohexanones / A.I.Ismiyev, A.M.Maherramov, V.A.Sukach, M.V.Vovk

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

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