الفهرس 
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Abstract
The present work includes the synthesis of some different
compounds derived from pyrrole. Thus on reaction of acetyl pyrrole
with CS2 it furnished the oxoketene gem-dithiol (2).
N
CH3 O
SH
SH
2
Dithiol (2) reacts with P2S5 in dry benzene and gives the 1,2-dithiol
3-thione (3).
N
CH3 S
S S
3
Reaction of (2) with salicyaldehyde in acetonitrile as a solvent
and marble as a catalyst and gives 2-mercapto-3-(1-methyl-1Hpyrrole-
2-carbonyl)chromen-4-one (4) while on reaction the (2) with
cinnamaldehyde and ethylcyanoacetate in tetrahydrofuran and drops
of glacial acetic acid it furnishes 2-Mercapto-3-(1-methyl-1Hpyrrole-
2-carbonyl)-4-oxo-6-phenyl cyclohexa-2,5-dienecarbonitrile
(5).
N
O Me
O
O
SH
N
CH3 O
HS
O
CN
Ph
4 5
On boiling (2) in xylene with p-benzoquione; 1,4-dichloronaphthoquinone;
cyclopentadiene or maleic anhydride it gives 2-[2-(1-
ii
methyl-1H-pyrrol-1-2yl)-2-oxoethylidene]-3a,7a-dihy-drobenzo[1,3]
dithiol-4,7-dione (6); 2-[2-(1-methyl-1H-pyrrol-1-2yl)-2-oxoethylidene]-
3a,9a-dihydronaphtho[2,3-d][1,3]dithiol-4,9-dione (7); 2-(2,4-dithiabicyclo[
3.2.1]octa-6-en-3-ylidene)-1-(1-methyl-1H-pyrrol-2yl)
ethanone (8) and 2-[2-(1-m-ethyl-1-H-pyrrol-2-yl)-2-oxo-ethylidene]
dihydro[1,3]dithiolo[4,5-c]furan-4,6-dione (9) respectively.
N
CH3
O
S
S
O
O
N
CH3 O
S
S
O
O
N
Me O
S
S
N
O
S
S
O
O
Me O
6
7
8 9
Treatment of (2) with malononitrile in THF/AcOH it gives
thiopyrane derivative (10) while on reaction of dithiol (2) with
thiosemicarbazide in refluxing ethanol, 3-mercapto-3-thiosemicarbazide-
1-(2-pyrr-olyl)-2-propenone (11) was obtained. Reaction of
dithiol (2) with indole in methylene chloride in the presence of monochloroacetic
acid it gave 3-(1H-indol-3-yl)-3-mercapto-1-(1-methyl-
1H-pyrrol-2-yl)propenone (12).
N
Me O
S
H N 2 NH2
S
N
Me O
NH
SH
N H
S
H N 2
H
N
Me
SH
O
NH
10
11 12
On treatment of (2) with guanidine sulphate in different conditions
it gives pyrimidine derivatives, thus when (2) reacts with guanidine
sulphate in ethanol in the presence of morpholine it gives 2-amino-6-
(1-methyl-1H-pyrrol-2-yl)-4-morpholin-4-yl-4,5-dihydropyrimidineiii
4-thiol (13) while reaction of dithiol (2) with guanidine sulphate in
ethanol in the presence of sodium methoxide it gives 4-ethoxy-6-(1-
methyl-1H-pyrrol-2-yl)pyrimidin-2-ylamine sulphate (14). On the
other hand reaction of dithiol (2) with hydroxyl amine hydrocholride
in ethanol or ethanol/AcOH it gives 3,3-bishydroxyamino-1-(methyl-
1H-pyrrol-2-yl)propenone hydrochloride (15) and N-[3-(methyl-
1H-pyrrol-2-yl)isothiazol-5-yl]hydroxylamine hydrochloride (16)
respectively.
N
O
N
Me N N
NH2
SH N
Me N N
OC2H5
NH2
N
Me
NHOH
NHOH
O
.HCl
N
Me
S
N NHOH
13
.H2SO4
14
15 16
.2HCl
Formylation of 1,2-dithione-3-thione (3) in the presence of DMF/
POCl3 it gives 5-(1-methyl-1H-pyrrol-2-yl)-3-thioxo-3H-[1,2]dithiol-
4-carbaldehyde (17). When 1,2-dithione-3-thione (3) was heated
under reflux with p-benzoquinone or 2,3-dichloro-1,4-naphthoquinone
it gives 2-[2-(1-methyl-1H-pyrrol-2-yl)-2thioxoethylidene]-3a,7adihydrobenzo[
1,3]dithiol-4,7-dione (18) and 3a,3a-dichloro-2-[2-(1-
methyl-1H-pyrrol-2-yl)-2-thioxoethylidene]-3a,9a-dihydronaphtho[2,
3-d][1,3]dithiol-4,9-dione (19) respectively.
S
S
N
CH3
S
CHO
N
Me S
S
S
O
O
N
Me S
S
S
O
O
Cl
Cl
17
18 19