Abstract
2-(2-Arylvinyl)-6-methyl-4-mercapto-5-acetylpyrimidine derivatives
3
a − d
, were synthesized form the reaction of the appropriate isothiocyanate derivatives
1
with α,
β
-unsaturated aminoketone
2
. Compound
3
was alkylated with methyl iodide, ethyl chloroacetate and/or bromosugar to afford
6
,
9
, and 22
a − c
respectively. Cyanoethylation of
3
b
afforded 6
b
which upon cyclization with hydrazine hydrate gave pyrazolopyrimidine
7
. Bromination of 6
b
gave dibromo compound
8
. Thieno[2,3-d]pyrimidines
10
and
12
were obtained by ring closure of the alkylated product
9
with TEA/EtOH and/or through cyclization of the hydrazide
11
with NaOEt/EtOH. While, Thieno[2,3-d]pyrimidine
14
was obtained directly by alkylation of
3
b
with chloroacetone in both TEA/EtOH and Na
2
CO
3
solution. The cycloaddition products
15
and
16
were obtained by reaction of
3b
with diethylmaleate and/or maleic anhydride. Formation of 1,3,4-oxadiazole
17
, pyrazoles
18
and
19
where obtained by treating the hydrazide
11
with carbon disulphide, triethyl orthoformate and acetylacetone respectively. While, reaction of
11
with p-chlorobenzaldehyde resulted in the Schiff's base
20
which, cyclizes with thioglycolic acid to afford thiazolidone
21
. Hydrolysis of
22
a − c
in TEA/MeOH afforded the free sugar
23
a − c
.
The structures of all the new compounds were confirmed using IR,
1
H, and
13
C NMR spectra and microanalysis. Selected members of the synthesized compound were screened for antimicrobial activity.