Abstract
Thieno [2,3-b] quinoline derivative
5
was synthesized by the cycloalkylation of compound bi 3a with chloro acetonitrile. Interaction of compound
5
with formic acid, formamide, and thioacetamide furnished the corresponding quinolino[3′,2′:4,5]thieno[3,2- d]pyrimidine derivatives
7
,
8
, and
9
, respectively. Also, quinolinothienopyrimidine
11
was obtained in good yield by cyclization of compound
5
with phenyl isothiocyanate under reflux in pyridine. Triethyl orthoformate reacted with compound
5
to form the ethoxymethylene derivative
12
. Refluxing of
5
with acetic anhydride for a short time afforded acetamide derivative
16
, whereas when refluxed for a long time furnished the diacetyl derivative
17
. Fusion of compound
5
with urea and thiourea yielded the corresponding quinolinothienopyrimidines
19
and
20
, respectively. When compound
5
was reacted with urea in the presence of sodium ethoxide, the corresponding ureado derivative
18
was obtained. Treatment of
5
with sulfuric acid at r.t. furnished the novel thienoquinoline
6
, while on heating gave the acid derivative
21
. Pyrido [2′,3′: 4,5]thieno [2,3- d] quinoline
23-25
were synthesized by the interaction of
5
with ethyl cyanoacetate, benzylidenemalononitrile, and acetaldehyde/malononitrile, respectively. On preliminary screening, compounds
22
and
25
exhibited in vitro growth that was inhibitory activity against Saccharomyces Cerevisiae when compared with the standard fungicide Mycostatine. The structure of the biologically active compounds
22
and
25
remain unchanged when exposed to gamma irradiation up to 40 KGy.