Hryhoriv H. Synthesis and biological activity of 2-amino-3-R-4H-pyrans based on 1,2-benzoxatiin-4(3H)-one 2,2-dioxide

The three-component interaction of 1,2-benzoxatiin-4(3H)-one 2,2-dioxide with active methylene nitriles and carbonyl compounds in order to synthesize new biologically active substances was investigated. 96 new compounds were obtained, among which are new condensed heterocyclic systems – 2-amino-4,6-dihydropyrano[3,2-c][2,1]benzoxatiine 5,5-dioxides and spiro[(4,6-dihydropyrano[3,2-c][2,1]benzoxatiin-5,5-dioxide)-4,3'-(indoline-2'-ones)]. New products for the investigated interaction were obtained for the first time, namely – triethylammonium salts of 3-(4-hydroxy-2,2-dioxido-2,1-benzoxatiin-3-yl)-2,1-benzoxatiine-5-olate 2,2-dioxides and 7-aryl-7,14-dihydrobenzo[5,6][1,2]oxatiino [4,3-b]benzo[5,6][1,2]oxatiino[3,4-e]pyridine 6,6,8,8-tetraoxide. The peculiarities of the carbonyl and nitrile components nature influence on the course of investigated interactions were revealed. The structure and individuality of the obtained compounds were confirmed by modern physico-chemical and instrumental methods, in particular, 1H and 13C NMR, IR spectroscopy, mass spectrometry and X-ray diffraction analysis. Wide research on the biological activity of the resulting substances has been carried out. The compounds with antibacterial, analgesic, anticoagulant and hemostatic properties were found.