2-метилімідазо[2,1-b][1,3]тіазолони, аміноліз, N-нуклеофіли, 1,1'-[дисуфанедіілбіс(пропан- 2,1-дііл)]біс-4-ариліден-2-(піролідин-1-іл)-1H-імідазол-5(4H)-они, 1,1'-[дисуфанедіілбіс(пропан-2,1-дііл)]біс-4- ариліден-2-морфоліно-1H-імідазол-5(4H)-они

Abstract

The work is devoted to the study of the regularities of the aminolysis reaction of pharmacologically promising type of imidazothiazole systems – 6,6-disubstituted and 6-arylidenesubstituted 2-methyl-2,3-dihydroimidazo[2,1-b][1,3] thiazol-5(6H)-ones. The chemical behavior of the latter was studied by interaction with secondary amines (pyrrolidine and morpholine) at room temperature, as well as with benzylamine at 10 hours boiling in toluene. As a result of the performed experiments it was found that 6,6-dimethyl-, 6,6-diphenyl- and 6-(propan-2-ylidene) substituted imidazothiazolones are resistant to amines both at room temperature and at high temperature treatment. Instead, 6-arylidene-2-methyl-2,3- dihydroimidazo[2,1-b][1,3]thiazol-5(6H)-ones were found to be labile to the action of N-nucleophiles at room temperature and undergo opening of the thiazolidine ring. with the formation of the corresponding 1,1'-[disufanediylbis(propane- 2,1-diyl)]bis-4-(benzylidene-, 4-bromobenzylidene-, 4-methylbenzylidene)-2-(pyrrolidin-1-yl)-1H-imidazol-5(4H)-ones and 1,1'-[disufanediylbis(propane-2,1-diyl)]bis-4-(benzylidene-, 4-methylbenzylidene)-2-morpholino-1H-imidazol- 5(4H)-ones with yields of 28–39%. Most likely, disulfides are formed from the corresponding mercaptoderivatives as primary products of aminolysis, which are oxidized by oxygen in the process. The composition and structure of the obtained products are unambiguously confirmed by complex physicochemical analysis, in particular by IR, 1H and 13C NMR spectroscopy, mass spectra, as well as elemental analysis data. It should be noted that compounds with the imidazol-5(4H)-one ring, which is part of the synthesized disulfides, are characterized by a widely range of biological activity. The discovery in a number of heterocycles of this type of compounds with antibacterial and anticancer activity, angiotensin II receptor antagonists, as well as the creation of chemosensors based on fluorescent proteins, is an important prerequisite for further biomedical studies of synthesized compounds.