Реакции электрофильного замещения и конденсации 5,6-дизамещенных-2,3- полиметилен-3,4-дигидротиено[2,3-d]пиримидин-4-онов

Аннотация

Subjects of research: 5,6-disubstituted-2,3-polymethylene-3,4- dihydrothieno[2,3-d]pyrimidin-4-ones, condensation products with aldehydes, products of acylation, bromination and oxidation. Purpose of work: studying of 5,6-dimcthyl-, tri-, tetra-, pcntamcthylcne-2,3-polymethylene-3,4-dihydrothieno[2,3 -d]pyrimidinc-4-ones interaction with benzaldehydes and furfurol, benzoyl chloride, bromine and nitrating acid; revealing of the factors influencing to passing of reactions; search of biologically active substances. Methods of research: fine organic synthesis, methods of IR-, *H NMR-, l3C NMR- spectroscopy, mass-spectrometry, X-ray, TLC. The results obtained and their novelty: for the first time systematic reactions of 5,6-disubstitutcd-2,3-polymethylene-3,4-dihydrothieno[2,3-d]pyrimidinc-4-ones with benzaldehydes and furfurol were investigated; the factors influencing to formation of a-arylidcnc- and a-(aryl-, hydroxy)mcthyldcrivatives arc determined. It is found, that interaction with benzoyl chloride yields only a-bcnzoyloxybcnzylidcn derivatives, and bromine - pcrbromidcs, which easy are transform in hydrobromides. It is found out, that CH3 group in position 5 at action of nitrating acid selectively oxidizes up to COOH groups. Practical value: the advanced method of synthesis of 2-amino-3-ethoxycarbonyl-4,5-polymethylenethiophenes, tri- and tetracyclic thieno[2,3-d]pyrimidinc- 4-ones is developed. The methods of synthesis a-arylidene- and a-(aryl-, hydroxy)mcthyl-, a-bcnzoyloxybcnzylidcn-5,6-disubstitutcd-2,3-polymethylcn-3,4-dihydrothicno[2,3-d]pyrimidin-4-ones and 5-carboxy-6-methyl-2,3-tri-, tctramcthylcnc-3,4-dihydrothicno[2,3-d]pyrimidine-4-oncs by condensation with aldehydes, benzoylation and interaction with nitrating acid of corresponding substrates arc created. Among of the synthesized substances the compounds possess high cytotoxic activity arc found. Degree of embed and economic effectivity: received results with aldehydes, benzoyl chloride, bromine and nitrating acid can be used for others N, S-hctcrocyclic compounds. Among of the synthesized substances the compounds with high cytotoxic activity arc revealed. Economic effectivity - social. Field of application: organic chemistry, medicine.