Взаимодействие 2,3-триметилен1,2,3,4-тетрагидрохиназолин-4-она и его гомологов с электрофильными реагентами

Аннотация

Subjects of the inquiry: 2,3-tri-,-tetra-,-penta-,-hexamcthylcnc-1,2,3,4-tetrahydroquinazolin-4-oncs. Aim of the inquiry: reduction of 2,3-polymctylen-3,4-dihydroquinazolin-4-ones by sodium borhydride, systematic study of acylation, carbamoylation, amidomcthylation and clcctrophyl substitution l,2,3,4-tctrahydroquinazolin-4-ones, revealing the optimum conditions reaction. Research of biological activity of synthesized compounds. Method the inquiry: organic synthesis, IR-, 'H-NMR-spcctroscopy, mass-spectrometry, TLC, X-RAY. The results achieved and their novelty: reception methods 2,3-polymctylene-l,2,3,4-tctrahcdroquinazolin-4-ones by reduction of 3,4-dihydroquinazolin-4-onc arc improved. It is shown that acylation, carbamoylation, amidomcthylation of them goes on atom of nitrogen N-l, leading corresponding 1-alcyl(aryl)amino(tio)carbamoyl-, -pyrrolidon-2-mcthyl derivatives. It is revealed that in reactions electrophyl substitution at relation 1:1 reaction goes to position C-6, i.e. the normal monosubstituted products arc formed, at relation 1:2 reaction goes unnormal, mentioning positions C-6, C-8 with simultaneous dehydrogenization -:NH-HC<-bonds, i.e. with formation of-:N=C<-doublc bond. Practical value: the designed methods of the obtaining 2,3-polymcthylcn-l,2,3,4-tctrahcdroquinazolin-4-ones, their 1-acyl-, -carbamoyl-, -pyrrolidon-2-mcthyl derivatives, as well as 6,8-disubstituted-2,3-polymethylen-3,4-dihydroquinazolin-4-ones, which is difficult to obtain by other methods. It is created way of the syntheses 6-monosubstituted-2,3-polymcthylen-l,2,3,4-tetrahydroquinazolin-4-ones. Amongst synthesized compounds arc revealed biologically active ones. Degree of embed and economical effectively: amongst synthesized compounds arc revealed compounds, possessing plant growing activity. In future they can find using as stimulators. Sphere of usage: organic chemistry, agriculture.