Abstract
5,5-Dimethylimidazolidine-2,4-dithione (
1
) undergoes a Mannich reaction to give 5,5-dimethyl-3-(4-morpholinomethyl)imidazolidine-2,4-dithione (
2
), which on treatment with (2,3,4,6-tetra-O-acetyl-α -D-glucopyranosyl)bromide (ABG) afforded 5,5-dimethyl-3(4-morpholinomethyl)-2-(2′,3′,4′,6′-tetra-O-acetyl-β -D-thioglucopyranosyl)-4-thiohydantoin (
3
). Oxidation of
3
with KMnO
4
furnished the corresponding sulfone
4
. Deblocking of
3
with sodium ethoxide afforded
1
. Reaction of
1
with ABG gave the N-glucoside
5
. Deblocking of
5
afforded 5,5-dimethyl-3-N-(3,4,5-trihydroxy-6-hydroxy-methyltetrahydropyran-2-yl)imidazolidine-2,4-dithione (
6
). Oxidation of
5
yielded 5,5-dimethyl-imidazolidine-3-N-(2′,3′,4′,6′-tetra-O-acetyl-β -D-glucopyranosyl)-2-oxo,4-thione (
7
). Reaction of
1
with phenacyl chloride afforded
8
, which on thiation with P
4
S
10
gave
9
. 5-Benzylidene-2-thioxoimidazolidin-4-one (
10
) reacted with some halo compounds and afforded
11
and
12
. Treatment of
10
with 2,4-dinitro-1-chlorobenzene afforded N,N-dimethyl-2,4-dinitrobenzamide (
13
) and 2-benzylidene-6-nitro-2H-benzo[d]imidazo[2,1-b]thiazol-3-one (
14
). Refluxing
12
with semicarbazides gave
15
and
16
. Boiling
12
with 4-aminoacetophenone furnished
18
, which on treatment with hydrazine gave 5-benzylidene-2-[4-(1-hydrazonoethyl)phenylimino]imidazolidin-4-one (
19
). Conden-sation of
18
with benzaldehyde yielded 5-benzylidene-2-[4-(3-phenylacryoyl)phenylimino]-imidazolidin-4-one (
20
).