Rudenko R. Reaction of N-arylmaleimides with 1,3-N,N-, C,N-, S,N-binucleophiles

Українська версія

Thesis for the degree of Candidate of Sciences (CSc)

State registration number

0412U002418

Applicant for

Specialization

  • 02.00.03 - Органічна хімія

17-04-2012

Specialized Academic Board

Д 64.051.14

V.N. Karazin Kharkiv National University

Essay

Investigation objects: N-arylmaleimides, 3-amino-1,2,4-triazole, 2-aminobenzimidazole, 5-aminopyrazoles, 6-aminouracils, hetarylthioamides, 3-mercapto-1,2,4-triazole, derivatives of pyrimidine, pyridine, imidazole fused with pirazole or triazole ring, pyrido[2,3-d]pyridine, derivatives of 2-(pyrazol-1-yl)-thiazole, derivatives of 3-hetaryl-1-arylpirrolidin-2,5-diones. Objectives: Studying of heterocyclizations of N-arylmaleimides with 1,3-N,N-, C,N-, S,N-binucleophiles, investigation of the structure of compounds prepared, studying of regularities of these reactions, the development of new methods of synthesis of some partially hydrogenated heterocycles based on mentioned reactions, the synthesis of new pyrimidine, pyridine, imidazole derivatives and other heterocycles. Research Methods and apparatus: organic synthesis, physical and chemical methods, spectral methods including NMR spectroscopy with NOE, mass spectrometry and X-ray diffraction. Theoretical and practical results: the selective preparation methods were developed for previously unknown partially hydrogenated derivatives of pyrimidine, pyridine, imidazole fused with azole or azine rings, tiazolone derivatives, 3-hetaryl-1-aryl-pyrrolidine- 2,5-diones and for instances of new heterocyclic system - 6H-chromeno[4',3':4,5]thiopirano[2,3-c]pyrrole- 1,3,6(2H, 3aH)-trione. Novelty: A comprehensive investigation of reactions of N-arylmaleimides with 1,3-N,N-, C,N-, S,N-binucleophiles was carried out; the method of preparation of the previously unknown heterocyclic compounds was proposed based on reactions studied; the investigation of derivatives of 5-aminopirazoles in their reactions with N-arylmaleimides was completed; the influence of reaction conditions on the direction of reactions of 3-amino-1,2,4-triazole, 2 aminobenzimidazole with N-arylmaleimides, the structures of the reaction products were proved reliably, a selective method for obtaining derivatives of triazolo[1,5-a]pyrimidine and triazolo[4,3-a]pyrimidine was proposed; the reaction of 6-aminouracils with N arylmaleimides was investigated comprehensively, reactions of N-arylmaleimides with 1,3-S,N heterocyclic binucleophiles were studied, the method of synthesis of 2-(pyrazol-1-yl)-thiazole was proposed; it was proved that the reaction of 3-mercapto- 1,2,4-triazole and N-arylmaleimides leads to the formation of 3-(1H-1,2,4-triazole-3-ylthio)-1-arylpirrolin- 2,5-diones, it was shown that the reaction of coumarin-3 carbothioamide with N arylmaleimidest leads to the formation of 6H-chromeno[4',3':4,5]thiopirano[2,3-c]pyrrole-1,3,6(2H,3aH)-triones. The degree of application: No. Scope (sectors) use: Laboratories and departments of various educational and research institutions that conduct the research on similar objects, and research centers on the detection and study of biologically active compounds.

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