Muravyova O. Multicomponent heterocyclization reaction of carbonyls and nitrogen-containing binucleophiles in synthesis of pyridine and pyrimidine derivatives

Українська версія

Thesis for the degree of Candidate of Sciences (CSc)

State registration number

0410U004654

Applicant for

Specialization

  • 02.00.03 - Органічна хімія

14-10-2010

Specialized Academic Board

Д 64.051.14

V.N. Karazin Kharkiv National University

Essay

Investigation objects: Alpha, beta-unsaturated ketone, acetoacetamides, aldehydes, barbituric acids, ammonia, aminoazole, 1,2,5,6-tetrahydropyrimidines, azolo[1,5-a]-pyrimidine-6-carboxamides, pyrazolo[4',3':5,6]pyrido-[2,3-d]pyrimidines, spiro[pyrazolo[3,4-b]pyridine-5,5'-pyrimidines]. Objectives: The main aim of the work was a study of objective laws of carrying of multicomponent heterocyclization reactions involving nitrogen containing binuclephiles and аlpha, beta-unsaturated ketones or 1,3-dicarbonyl compounds, development of methods of tuning their direction for selective synthesis of partially hydrogenated derivatives of pyridine and pyrimidine. Methods and apparatus: organic synthesis, NMR spectroscopy, mass- spectrometry, X-ray analysis, liquid chromatography (HPLC), elemental analysis. Theoretical and practical results: High-selective and convenient synthetic methods for new partially hydrogenated derivatives of pyridine and pyrimidine were developed; possi! ble ways of further modification of these compounds; new four-component reaction was discovered for synthesis of new heterocycles. Novelty: on the basis of multicomponent reaction of аlpha, beta-unsaturated ketones, carbonyls and ammonia it was proposed and developed a method of synthesis of 2,(2),4,6-tri(tetra)aryl(hetaryl)-substituted 1,2,5,6-tetrahydropyrimidines and 1,5,9-triazaspiro[5.5]undec-1-enes; a dependence of carrying three-component reactions of acetoacetamides and aldehydes with 3-amino-1,2,4-triazoles or 4-substituted 5-aminopyrazoles on treatment parameters was studied; three-component reaction of barbituric acids with 5-aminopyrazoles and aldehydes leading to derivatives of pyrazolo[4',3':5,6]pyrido[2,3-d]pyrimidine-5-one was studied; by four-component reaction of barbituric acids, 5-aminopyrazoles and aldehydes novel class of heterocyclic compounds. On the basis of reaction of аlpha, beta-unsaturated ketones, carbonyls and ammonia under ultrasonic irradiat! ion new facile method of synthesis of 2,(2),4,6-tri(tetra)substituted 1,2,5,6-tetrahydropyrimidines was developed. The degree of application: Act of application in department of heterocyclic chemistry (department 0205), SSD of functional materials chemistry SSI "Institute for Single Crystals" NAS of Ukraine from 08.10.2009 y. Scope (sectors) use: Laboratories and the Department of various primary and research departments, which conducted a study similar topics facilities and research centers for the study of biologically active compounds.

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