Синтез та реакції діацетил(діалкоксикарбоніл)заміщених гідроксициклогексанонів / А.І.Ісмієв, А.М.Магеррамов, В.А.Сукач, М.В.Вовк

• Date: 2016
• Main Authors: Ismiyev, A. I., Maherramov, A. M., Sukach, V. A., Vovk, M. V.
• Format: Article
• Language: Russian
• Published: National University of Pharmacy 2016
• Subjects: гідроксициклогексанони; дикетонна конденсація; таутомерія; анелювання; дегідратація; ароматизація; УДК 547.593.2 547.594.3 547.595.6
• Online Access: https://ophcj.nuph.edu.ua/article/view/ophcj.16.905
• Journal Title: Journal of Organic and Pharmaceutical Chemistry

The 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 representatives of carbofused heterocycles, such as isoxazoles, pyrazoles, triazolo[3,4-b] quinazolines, thieno[2,3-c]isoquinolines and pyrazolo[3,4-c]isoquinolines. The importance of oxidation, dehydration and aromatization processes of hydroxycyclohexanones for organic synthesis has been emphasized.