Vlasov S. Synthesis and reactivity of 3-heterylcoumarins with azole and azine moieties

Investigation objects: The derivatives of 3-heterylcoumarins obtained on the basis of 2Н-[1]benzopyran transformations. Purpose: The development of methods for 3-heterylcoumarin's with azole and azine moieties synthesis, based on recyclization of 2-iminocoumarin-3-carboxamides and reactions of 3-(alfa-bromoacetyl)coumarins. Methods: The methods of organic synthesis, 1H NMR-, IR-, UV-spectroscopy, chromato-mass-spectrometry, X-ray diffraction analysis and 13C NMR; quantum-chemical semi-empirical calculations methods; the biological activity has been studied according to the methods recommended by Pharmacological committee MH of Ukraine. Scientific novelty: The novel approaches for the synthesis of 3-hetrylcoumarins with thieno[2,3-d]pyrimidine-4-one and 3Н-quinazolin-4-thione moieties via reccylization of 2-iminocoumarin-3-carboxamides have been studied. The synthesis of novel 3-(4-chloro-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine-2-yl)coumarins and the their application as the starting compounds in the efficient synthetic route for 3-(4-thioxo-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine-2-yl)coumarins have been suggested. The novel derivatives of 3-(coumarin-3-yl)-2H,6H-pyrimido[2,1-b][1,3,4]thiadiazine-6-ones and 3-(7-R-imidazo[2,1-b]benzothiazol-2-yl)coumarins were obtained. The novel liquid-phase parallel method of the combinatorial library of 3-[4-(R-coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acids amides synthesis has been developed. Degree of application: The data obtained in the course of the work is used in the research work of The Central Scientific Research Laboratory of NUPh (Kharkiv) and the research investigations of The Laboratory of Antimicrobial Remedies of the Mechnikov Institute of Microbiology and Immunology (Kharkiv).