Publication details
Syntéza nového 4H-benzo[1,2,4]dithiazinového skeletu a studium jeho elektrochemického chování
| Title in English | Synthesis of novel 4H-benzo[1,2,4]dithiazine system and studies of their electrochemical behaviour |
|---|---|
| Authors | |
| Year of publication | 2003 |
| Type | Article in Periodical |
| Magazine / Source | CHEMICKÉ LISTY |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Keywords | 4H-benzo[1;2;4]dithiazine system; scavengers of free radicals; sheme of preparation; 2-aminothiofenol ; alkyl-; acyl; and arylisothiocyanate application; RA; NMR; FTIR and MS identification of 4H-benzo[1;2;4]dithiazine derivatives |
| Description | Compounds containing the S-S bond in molecules could be potential scavengers of free radicals in organisms, because the bond chalcogen-chalcogen may be liable to the reversible redox ring-opening and ring-closure. Free radicals damage tissues, cells, and the whole immunity system of human body and cause many types of cerebrovascular, cardiovascular, and oncological diseases, respectively. Now we found a method for preparation of the new benzo[1,2,4]dithiazine skeleton. We use 2-aminothiophenol as a precursor for synthesis of this skeleton. 2-Amino-thiophenol reacts with alkyl-, aryl-, and acylisothiocyanates in the first step of the synthesis. In accord with literature we found that the application of 2-aminothiophenol and acylisothiocyanate in equimolar amount proceeded to thiurea derivatives. Now we elucidated the existence of these products in isothioureido form. On the other hand, an excess of acylisothiocyanate evoked reaction on both functional, i.e. amino and sulfanyl, groups. In the case of alkyl- and arylisothiocyanates, 2-aminothiophenol reacts only on amino group, in excess too. If we carried out reaction of 2-aminothiophenol with phenylisothiocyanates at room temperature, we observed elimination of sulfane and a formation of thiazole system. The desired compound, 1-(2-sulfanylphenyl)-3-phenylthiourea, was obtained by the carrying out of the reaction at zero C. Reaction of 2-aminothiophenol with methyl- and allylisothiocyanates was realized analogously and corresponding 1-(2-sulfanylphenyl)-R-thioureas were formed. |
| Related projects: |