The reactions with amines of disulphides derived from thiazolium salts. Part I. Primary and secondary amines
作者:R. G. Cooks、P. Sykes
DOI:10.1039/j39680002864
日期:——
The reaction with primary amines of disulphides derived from base-catalysed ring-opening of thiazolium salts proceeds by nucleophilic cleavage of the disulphide bond and enamine formation, and finally yields an imidazoline-thione as major product. Evidence for this mode of amine attack and for the presence of enamine and enethiol intermediates was found in the reaction of various modified disulphides
3-Methylbenzothiazolium salts were allowed to react with superoxide to afford dimeric bis[o-(N-formyl-N-methylamino)phenyl]disulfides and 3-methyl-2-benzothiazolones. The reaction was applied to monocyclic thiazolium salts, and novel ten-membered ring compounds were formed whose structures were elucidated by X-ray crystallographic analysis. These results prompted us to alternative synthesis of the