O‘zbekiston respublikasi oliy taʼlim, fan va innovatsiyalar vazirligi urganch davlat universiteti

"Alkylation, acylation and chlorination reactions of quinazolon-4-yl-2-thiocarboxylic acid anilide" by Rozmetova Sevara Oktambayevna, second-year graduate student of UrDU
ANNOTATION
Quinazoline derivatives are of great importance both theoretically and practically. Among them, biologically active substances for agriculture (fungicides, bactericides and plant growth stimulants) were found. For example, KMAX fungicide and Nikamizolon bactericide were created in the department of organic synthesis of UzR FA O'MKI, and they are recommended for use in agriculture. At the same time, most of the compounds of this class are used as medicines. Deoxypeganin, extracted from the Peganum harmala plant and obtained synthetically, is used in medicine as an anticholinesterase drug. The presence of several active centers in the molecule of quinazoline thioamides, including: a thioamide (C=S) group in position 2, endocyclic and exocyclic nitrogen atoms in positions 1 and 3, a carbonyl group and a benzene ring at C-4 make these compounds electrophilic and nucleophilic. indicates that exchange reactions can be carried out at one or more reaction centers.
Studying the reactions of thioimide salts formed when thioamides are alkylated with aliphatic diamines (ethylenediamine, hexamethylenediamine), o-substituted aromatic amines (o-aminophenol, o-phenylenediamine, o-aminothiophenol), simultaneous formation of two heterorings (quinazolone, etc. heteroring ) synthesis of heterocyclic compounds, determining the direction of the studied reactions, and searching for biologically active compounds based on the synthesized substances show the relevance of this work.
This master's thesis is devoted to the study of alkylation, acylation and chlorination reactions of quinazo lon-4-yl-2-thiocarboxylic acid anilide and to determine the laws of the reactions and to search for biologically active substances among the synthesized compounds.
For the first time, the synthesis and chemical transformations of -(quinazolon-4-yl-2)-N-phenyl-S-alkyl (benzyl) thioimide salts and quinazolon-4-yl-2-thiocarboxylic acid anilidine were systematically studied; the main laws of reactions involving electrophilic and nucleophilic reagents have been determined.
Alkylation reaction of thioamides of quinazoline derivatives with alkyl halides in absolute acetone was carried out, synthesis of thioimide salts of quinazolone derivatives was carried out.
When the reaction of quinazolon-4-yl-2-thiocarboxylic acid anilide with acetyl- and benzoyl chlorides is carried out at low temperature in pyridine, the reaction selectively goes to the exocyclic nitrogen atom, and when acylating thioamide salts (sodium, potassium), the reaction is relatively polar and soft center - S- atom departure is indicated.
Chlorination reactions of quinazolon-4-yl-2-thiocarboxylic acid anilide were studied.

Scientific Supervisor: _____________ PhD., docent. Y.R.Takhirov

Master Student: _____________ S.O.Rozmetova