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Registration Number

0219U101853, 0115U004731 , R & D reports

Title

Synthesis of heterocyclic compounds on the basis of N-substituted 1,4-quinoneimines.

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Head

Avdeenko Anatoly P., Кандидат хімічних наук

Registration Date

15-11-2019

Organization

Donbass State Engineering Academy

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Object of research: unsubstituted and halogensubstituted in the quinoid ring N- acyl(acety)l -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 acyl(acetyl) 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-acyl((acetyl) -1,4-benzoquinoniminoimines were synthesized. Their structures were proved by the spectral (IR, PMR, NMR 13C) data and elemental analysis. In the interaction of N -acetyl-1,4-benzoquinone monoimin with potassium rhodanite, depending on the energy of the LUMO of the original quinone monoimin, benzo [d] [1,3] oxathiol-2-ones and benzo [d] oxazol-2 (3H) - derivatives were obtained thiones. At the first stage of the reaction, the high value of the energy of the LUMO promotes the addition of rodanide ion to the nitrogen atom, the low value to the addition by the sulfur atom.. As a result of the action of bromine on the halogen-containing N-acetyl -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. Efficiency of introduction: heterocyclic compounds based on 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.

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2020-04-02