Abstract
2-(2-thioxo-4-oxo-thiazolidin-3-yl-)-6-(4-nitrophenylthio)-benzthiazole
1
was prepared and condensed with two moles of aromatic amine to give the corresponding 2,4-diarylimino thiazolidines
2
a-b
. The latter compounds undergo cycloaddition reaction with chloroacetylchloride and thioglycolic acid to give spiro compounds
5
a-b
and
6
a-b
The reaction of
1
with hydrazine hydrate afforded 2-hydrazono compound
3
. Reaction of
3
with phenyl isothiocyanate gave the corresponding thiosemicarbazone
9
. Cyclocondensation of chloroacetic acid with
9
afforded compound
10
. Also, condensation of
3
with aromatic aldehydes gave the corresponding Schiff's bases
11
a-c
. Reaction of compound
1
with malononitrile gave compound
4
which was reacted with sulfur in presence of diethylamine to give thienothiazole derivative
14
. Compound
4
was reacted also with carbon disulfide in presence of triethylamine to afford thiopyranthione
15
. Furthermore, the active methylene of
4
couples with benzene diazonium chloride followed by cyclization to give thiazolopyridazine derivative
17
. Oxidation of compounds
5
a-b
,
6
a-b
,
10
,
11
a-c
,
14
,
15
and
17
using H
2
O
2
/ACOH mixture afforded the corresponding diarylsulfones
7
a-b
,
8
a-b
,
12
,
13
a-c
,
18
,
19
and
20
.