Synthesis of new hybrid 1,4-thiazinyl-1,2,3-dithiazolyl radicals <i>via</i> Smiles rearrangement
作者:Petra Vasko、Juha Hurmalainen、Akseli Mansikkamäki、Anssi Peuronen、Aaron Mailman、Heikki M. Tuononen
DOI:10.1039/c7dt03243a
日期:——
The condensation reaction of 2-aminobenzenethiols and 3-aminopyrazinethiols with 2-amino-6-fluoro-N-methylpyridinium triflate afforded thioether derivatives that were found to undergo Smilesrearrangement and cyclocondensation with sulphur monochloride to yield new hybrid 1,4-thiazine-1,2,3-dithiazolylium cations. The synthesized cations were readily reduced to the corresponding stable neutral radicals
Thiazolopyrazines having growth inhibitory activity against microorganisms are of the formula ##STR1## wherein X is --Br, --Cl or F and R is --H or --CH.sub.3-x Y.sub.x, Y is --Br, --Cl, or F and x is 0, 1, 2 or 3. These compounds also have utility as intermediates for the preparation of three-ring compounds which are highly active against microorganisms.