Tarasiuk T. New functional derivatives of benzothiazepines and benzoxathiepines

The thesis is devoted to the synthesis of 4,5-dihydro-1,4-benzothiazepine-3(2Н)-, 1,5- dihydro-4,1- benzothiazepine-2(3Н)-, 2H-1,5-benzoxathiepine-3(4H)- and 5H-4,1-benzoxathiepine-3(2H)-one derivatives, their chemical properties investigation and the determination of structures of new compounds. It has been developed two new alternative methods for the synthesis of 1,4-benzothiazepine derivatives. The best of them has been patented. It has been found optimal conditions for oxidation of sulfide fragment of 1,4- and 4,1-benzothiazepine derivatives into corresponding sulfones. The regioselectivity of reactions with electrophilic reagents: bromine, DMFDMA and Vilsmeier reagent has been investigated and compared. Position 7 of 1,4-benzothiazepine system has been functionalized. А new method for the synthesis of 2H-1,5-benzoxathiepine-3(4H)-ones has been developed. A number of reactions of methylene (synthesis of dimethylaminomethylidene derivatives) and carbonyl (reduction; condensation with hydroxylamine, hydrazines; protection by ketals; Strecker, Horner - Wadsworth - Emmons and Corey - Chaykovsky reactions) groups have been conducted. It was found and explained general trends in ring contraction rearrangements of 1,5-benzoxathiepine system. А selective method of oxidation of 2H-1,5-benzoxathiepine-3(4H)-one into sulfoxide has been developed. First time it was synthesized 5H-4,1-benzoxathiepine-3(2H)-one.