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Information × Registration Number 0218U003862, 0115U004731 , R & D reports Title Synthesis of heterocyclic compounds on the basis of N-substituted 1,4-quinoneimines. popup.stage_title Head Avdeenko Anatoly Petrovich, Кандидат хімічних наук Registration Date 14-08-2018 Organization Donbass State Engineering Academy popup.description2 Object of research: unsubstituted and halogensubstituted in the quinoid ring N-aryl- and N- acyl-1,4-benzoquinoneimines. Objective of research: to find the rules of the influence of the steric and donor-acceptor properties of the substituents near the nitrogen atom in N-aryl- and N acyl 1,4-benzoquinonemjnoimines on their reactivity to nucleophiles, and also the synthesis of new heterocyclic potentially bioactive compounds on their basis. Research methods: organic synthesis, physical and chemical methods for the investigation of organic compounds: IR, NMR 1H, NMR 13C spectroscopy, elemental analysis, X-ray diffraction analysis, thin layer and column chromatography. Theoretical and practical results: new heterocyclic compounds on the basis of N-aryl and N-acyl-1,4-benzoquinoniminoimines were synthesized. Their structures were proved by the spectral (IR, PMR, NMR 13C) data and elemental analysis. As a result of the action of bromine on the halogen-containing N-acetyl (aroyl) -1,4-benzoquinoniminoimines having one free position of 3 or 5 of the quinidic nucleus, 6-hydroxy-2-methyl(aryl)-1,3-benzoxazoles are obtained, which is quite a simple method of synthesis of the latter. As a result of the reaction of N-acyl-1,4-benzoquinonemonimines with enamines, in particular 4-(p-toluidino pent-3-en-2-one and ethyl 3-(phenylamino)bute-2-enoate, by the mechanism of the reaction of Nenitsesku, derivatives of benzofuran were obtained. The probable mechanisms of this reaction are studied. Also, the influence of solvents of various nature (acetic acid, dichloroethane) on the course of the cyclization reaction was investigated and it was found that benzofuran derivatives are the only heterocyclic products. The results of the work extend synthetic possibilities of synthesis of new heterocyclic compounds on the basis of N-substituted 1,4-benzoquinonines. Efficiency of introduction: heterocyclic compounds based on N-aryl- and N-acyl-1,4-benzoquinonmonoimines are potential biologically active compounds and can be used as drugs, pesticides. Application area: in the general and special courses of organic chemistry in classical universities. The products obtained in this work can be tested as new drugs. Product Description popup.authors Авдєєнко Анатолій Петрович Коновалова Світлана Олексіївна Лахтаренко Наталія Василівна Лисенко Олена Миколаївна Марченко Інна Леонідівна Санталова Ганна Олександрівна Холмовой Юрій Петрович Юсіна Ганна Леонідівна popup.nrat_date 2020-04-02 Close