АЦИЛИРОВАНИЕ И ХЛОРСУЛЬФОНИЛИРОВАНИЕ ХИНАЗОЛИН-2,4-ДИОНОВ

Аннотация

Subjects of research: quinazolin-2,4-diones. Purpose of work: a systematic studing of the reactions of acylation and chlorosulphonation of quinazolin-2,4-diones. Revealing of the factors influencing to a course and a direction of acylation and chlorosulphonation reactions. Development of convenient, effective methods of the synthesis of derivatives quinazolin-2,4-dionc and search for biologically activity compounds among them. Methods of research: fine organic syntheses, methods of IR-, NMR 'Н spectroscopy, mass-spectrometry, TLC, X-ray. The results obtained and their novelty: for the first time, an acylation of quinazolin-2,4-diones with aromatic acid chlorides in the presence 1-10'2 mol of Lewis acids was investigated and the factors influencing to a course and a direction of reactions is determined. The relative activity series of 4-substitutcd bcnzoylchlorides and catalysts in the reactions of catalytic acylation of quinazolin-2,4-diones have been established. It was found that in reactions of quinazolin-2,4-diones with chlorosulphonic acid chlorosulphonylic group is directed to 6-position of quinazolin-2,4-diones, in the case of 6-bromoquinazolin-2,4-diones to the position 8. It gives possibility of synthesis of 6- and 8-chlorosulphonylquinazolin-2,4-diones. Practical value: in the result of conducted studies the possibility of syntheses of 6-acylquinazolin-2,4-diones, 6-chlorosulphonylquinazolin-2,4-diones, 6-bromo-8-chlorosulphonylquinazolin-2,4-dione, 6-mcrcapto- and 6-bromo-8- mcrcaptoquinazolin-2,4-diones, 2,4-dioxoquinazolin-6- and 6-bromo-2,4-dioxoquinazolin-8-sulphoacids, their amides and esters arc shown. The preparative method for syntheses 6-chlorosulphonylquinazolin-2,4-diones were developed. Among synthesized compounds the biologically active substances arc revealed. Degree of embed and economic effectivity: among synthesized compounds arc revealed substances, which posses plant growing and herbicide activities. In future they can find using in agriculture. Field of application: organic chemistry, agriculture.