Alkylation of Thiohydantoins Including Synthesis, Conformational and Configurational Studies of Some Acetylated S-Pyranosides.

5-Benzylidene-2-thiohydantoin ( 1 ) and 5,5-dimethyl-2,4-dithiohydantoin ( 6 ) undergo Mannich reaction with formaldehyde and morpholine to give the corresponding Mannich products 2 and 7 , respectively. Subsequent reaction of the product 2 and 7 with phenacyl bromide gives the corresponding 2-benzolmethylthiohydantoin Reactionof 5-benzylidene-2-carbomethoxythiohydantoin ( 5b ) with P 2 S 5 afforded 4-benzylideneimidazo[2,1-b]-thiazole-2-thione-5-one ( 13 ) as the sole product. Reaction of 2-thio and 2,4-dithiohydantoin derivatives 2 and 7 with (2,3,4,6-tetra- O -acetyl-α-D-gluco- or galgctopyranosyl) bromide or (2,3,4-tri- O -acetyl-α-xylopyranosyl) bromide afforded the corresponding S-glucogalacto- or xylosides ( 14-19 ). Many attempts to deacetylation of the resulting S-nucleosides and to get N-nucleosides were tried. [ABSTRACT FROM AUTHOR]