A novel synthesis of sulfone systems as antimicrobial agents

Article abstract of DOI:10.1515/znb-2000-0119

The applicability and synthetic potency of novel reagent, 2-aryl-1,1-dicyano-3-(phenylsulfonyl)propenes 3 to develop an expeditious convenient synthetic route of unique polyfunctionally substituted carbocyclic and heterocyclic sulfone systems is reported. Chemical and spectroscopic evidence for the structures of the newly synthesized compounds are described. Some of the obtained compounds were tested for their antimicrobial activity.

Full text of DOI:10.1515/znb-2000-0119

A Novel Synthesis of Sulfone Systems as Antimicrobial Agents
Ayman W. Erian3, Yvette A. Issacb, and Sherif M. Sherif3
a Department of Chemistry, Faculty of Science, Cairo University Giza, Egypt
b Department of Chemistry, Faculty of Science, Benha University, Benha, Egypt
Reprint requests to Dr. Y. Issac
Z. Naturforsch. 55b, 127-132 (2000); received August 3, 1999
Sulfone Systems, Antimicrobial Agents
The applicability and synthetic potency of novel reagent, 2-aryl-l,l-dicyano-3-(phenylsulfo-
nyl)propenes 3 to develop an expeditious convenient synthetic route of unique polyfunction-
ally substituted carbocyclic and heterocyclic sulfone systems is reported. Chemical and spec-
troscopic evidence for the structures of the newly synthesized compounds are described.
Some of the obtained compounds were tested for their antimicrobial activity.
Introduction
lution to furnish the target novel key reagent 3 in
acceptable yields (Scheme 1). The elemental and
spectroscopic data of 3 are entirely compatible
with the assigned structure.
In view of the diverse biological and physiologi-
cal activities of sulfones [1-7], and in connection
with our previous efforts directed towards the fac-
ile synthesis of heterocyclic ring systems [8- 12],
we designed a specific simple program aimed at
the development of convenient synthetic approach
for the construction of several new hitherto unre-
ported carbocyclic and heterocyclic sulfone sys-
tems of expected potential bioresponses utilizing
the novel reagent 3 as a unique key precursor. The
newly synthesized derivatives possess latent func-
tional substituents and appear to be promising for
further chemical transformations as well as biolog-
ical activity evaluations.
NC^^CN
NC
,CHp
- V
S02Ph
S02Ph
NC
Ar
O
fi
4
Ar^XH3
N a S 0 2Ph
NC^^CN
NBS
cci4
Br
Y
X
A r ''”
CH3
5
Ar
Ph
2-6
a
Investigations, Results and Discussion
C6H4Cl-4
b
Our attempts to prepare the key precursor, 2-
aryl-l,l-dicyano-3- phenylsulfonylpropenes 3, via
condensation of equimolar amounts of malononit-
rile 1 with the appropriate phenylsulfonylaceto-
phenones 2 utilizing a variety of acidic or alkaline
conditions were unsuccessful. In our hands, the
precursor 3 could be prepared stepwise. Thus, con-
densation of 1 with the appropriate acetophenones
Scheme 1
Com pound
3 proved to be highly reactive
towards various reagents and underwent num er-
ous chemical transformations, resulting in the con-
struction of a wide range of carbocyclic and het-
erocyclic aromatic sulfone systems. Thus, when
equim olar amounts of each of 3a,b and elemental
4 afforded the corresponding condensation pro- sulfur in dioxane were heated under reflux, 2-
ducts 5 [5,13], which could be brom inated with N-
bromosuccinimide in carbon tetrachloride solution
in the presence of a catalytic amount of benzoyl
peroxide to afford the corresponding a-brom o de-
rivatives 6. The latter reacted with equimolar
amounts of sodium benzenesulfinate in ethanol so-
amino-4-aryl-5-phenylsulfonylthiophene-3-carbo-
nitriles could be isolated in good yields
(Scheme 2).
The methylene group in 3 proved to be highly
reactive towards electrophilic reagents. Thus, com-
pound 3a reacted with an equimolar amount of the
7
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D
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A. W. Erian et al. • A Novel Synthesis of Sulfone Systems as Antimicrobial Agents
128
Ar
CN
appropriate aromatic aldehyde in dioxane contain-
ing potassium r-butoxide to afford the correspond-
ing pyran derivatives 10 instead of the expected
arylidene derivatives 8. The reaction apparently
involves form ation of the hydroxy interm ediate 9,
intram olecular heterocyclization via an anticipated
Michael-type addition of the O H group to the CN
function and spontaneous autoxidation via loss of
hydrogen molecule under the experimental reac-
tion conditions to give the final isolable products
10. Similar autoxidations have been reported pre-
viously [5,14-16]. Both elemental analyses and
spectral data are in agreement with the proposed
structure 10. Thus the IR spectrum of 10a as a
representative example, displayed an NH absorp-
tion peak near 3436 cm -1 and only one CN ab-
sorption band at 2220 cm“1. Its *H NMR spectrum
(DM SO-d6) showed beside the aromatic protons
signal at r3 = 6.92-7.80 ppm, a singlet at (5 =
12.4 ppm corresponding to a NH function.
Alternatively, compound 10a could be prepared
via an independent route involving the reaction of
3a with equim olar amount of benzoyl chloride in
pyridine, under reflux, to afford a single product
which was found to be identical in all aspects
(m.p., mixed m.p. and IR data) with 10a, appa-
rently via intermediacy of the benzoyl derivative
11.
NC^ XN
X
i -
Ph02S -^ \s/ ^ NH2
7
Ph
y
Ar
|
1/8 S8
S02Ph
S02Ph
NC.
XN
if °H
P h ^ ^ p ^ A r
S02Ph
9
-H,
NC^ XN
Ph
Ph
S02Ph
11
S02Ph
Ar
10
7-10
Ph
a
C6H4Cl-4
b
Scheme 2
the corresponding coupling products 5-(phenyl-
azo)cyclopentadiene derivatives 14a,b.
The reaction of each of 3a,b with equimolar
As an extension of the synthetic route the beha-
amounts of phenacyl bromide in dry dioxane in
the presence of potassium f-butoxide, under re- vior of 12 in cycloaddition reactions was investi-
gated, and it was found to be a highly reactive can-
didate in [4+2] cycloaddition reactions with
electronpoor jr-deficient systems. Thus compounds
12a,b add equim olar amounts of dimethyl acety-
lenedicarboxylate in dry acetonitrile to furnish the
corresponding norbornadiene 15. (Scheme 3).
Both elemental analysis and spectroscopic data of
15 are consistent with the assigned structure. Thus,
the mass spectrum of 15a revealed a molecular ion
peak at m/z 568 corresponding to the molecular
flux, afforded the corresponding 5-(phenylsul-
fonyl)cyclopentadiene-2-carbonitrile derivatives
12a,b, respectively (Scheme 3). Assignment of
structure 12 for the reaction products was based
on analytical and spectral data. Thus, as an exam -
ple, the IR spectrum of 12a showed absorption
bands at v 3400, 3300 (NH2), 2220 (CN) and 1695
(CO) cm -1. Its 'H NMR spectrum (DM SO-d6)
showed a singlet at d = 3.92 for NH 2 protons, sin-
glet at d ~ 4.42 for methine proton in addition to
a multiplet at <5 = 6.71-7.80 for the aromatic pro- formula C31H 24N20 7S. Its IR spectrum showed
absorption peaks at v 3400, 3290, (NH2), 2219
(CN) and 1680, 1675, 1672 (3 CO) cm -1. Similarly,
compounds 12a,b add to equimolar amounts of
tetracyanoethylene in dry acetonitrile to give the
corresponding [4+2] cycloadducts 16a,b respec-
tively.
tons.
Compound 3a reacted with two-fold molar
equivalent of phenacyl bromide under the same
experimental conditions to yield the 5-phenacyl
derivatives of 12a cyclopentadiene 13.
Compounds 12a,b reacted with equimolar
amounts of phenyldiazonium chloride in ethanolic
sodium acetate solution (pH —8) at 0 -5 °C to yield
In summary, the results presented in this article
dem onstrate a general simple applicable method-
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A. W. Erian et al. ■A Novel Synthesis of Sulfone Systems as Antimicrobial Agents
129
NC
NH,
Antim icrobial Activity
Y i
Table I shows the antimicrobial activity of some
of the above mentioned compounds against a vari-
ety of bacteria and yeast. Also, in the same table
there is a comparison between the activity of these
compounds and some known antimicrobial agents.
The microbial activity of the compounds consid-
ered were tested on the Gram negative bacteria
Salmonella typhimurium CAIM 1350, Pseudomo-
nas spp. CAIM 13, Shigalla, Brodiatella; the Gram
positive bacteria Bacillus subtilis CAIM 1007,
Staphylococcus aureus CAIM 1352, Micrococcus
lutea, and the yeast Candida albicans CAIM 22,
and Saccharomyces cerevisiae CAIM 14.
P
h ^ \ / ^ - C
O
P h
Ph02S
CH2COPh
13
NC
NH,
Ph02S
Ar—
'C O P h
Ph02S
H
12
Ph— N= N CI
All strains were kindly supplied from M icrobio-
logical Research Center, Cairo-Mircen, Egypt
(CAIM ). Bacterial test organisms were inoculated
on nutrient agar slants for 24 h at 37 °C. Yeast
organisms were inoculated on molt extract agar
slants and incubated at 28 °C for 48 h.
H
NC
NH2
Ph02S-_ i
COPh
NH,
M6O2C
rX^ \ / ^i- C- O
Ph02S
A
P
h
N=NPh
M e 0 2C
^
Ar-
Ar
Ph
3-16
a
14
15
Q,H4CI-4
b
Experim ental
Scheme 3
Melting points are uncorrected. IR spectra were
recorded (KBr) on a Pye Unicam SP-1000 spectro-
photom eter. !H NMR spectra were obtained on
Varian Gemini 200 MHz spectrom eter using TMS
as internal reference. Chemical shifts are ex-
pressed as <5 (ppm). Mass spectra were recorded
on a GCM S-QP 1000 EX mass spectrom eter oper-
ating at 70 eV. The elemental analyses were per-
form ed by the Microanalytical Unit, Cairo Univer-
sity.
ology for the construction of a wide variety of
polyfunctionally substituted carbocyclic and het-
erocyclic sulfone systems obtainable only with dif-
ficulty otherwise. The importance of such deriva-
tives is due to their expected wide spectrum of
potential bioresponses. Work along the expansion
of such synthetic approach is now in progress.
Table I. Antimicrobial activity of compounds considered against bacteria and yeast (diameter of inhibition zones
in mm).
Compound
Salm.
Pseudo.
Staph.
Cand.
Sac.
Bacil.
_
_
3b
7
10a
10b
12b
15a
16a
16
29
12
15
20
16
11
25
25
-
9
-
12
20
7
7
18
8
-
-
-
-
-
30
10
11
20
19
13
30
40
-
-
-
8
12
18
8
11
27
26
10
15
15
15
-
18
12
15
25
24
-
-
2
-
17
-
-
-
-
-
Tetracycline
Gentamycine
Chloramphenicol
Ampicillin sodium
Ampicillin anhydrous
Amoxacillin trihydrate
-
-
-
23
20
25
12
10
15
12
15
10
-
-
-
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130
A. W. Erian et al. ■A Novel Synthesis of Sulfone Systems as Antimicrobial Agents
2-Aryl-l,l-dicyano-3-(phen\lsulfonyl)propenes
2-Amino-4-phenyl-5-(phenylsulfonyl)thiophene-3-
(3a,b)
carbonitrile (7a)
Yield: 55%; m.p. 295 °C (dioxane). - IR: v -
3400, 3320 cm“ 1(N H 2),2222 c ir r 1(CN), 1640 cm “ 1
(C=C). - !H NM R (DM SO-d6): (3 = 6.25 (s,2H,
N H 2), 6.71-6.95 (m, 5H, aromatic-H), 7.40-7.80
(m, 5H, S 0 2Ph). - MS (70 eV): m/z (%): 340
(22) [M+],
General procedure: To a solution of 5a,b (0.1
mol) [5] in carbon tetrachloride (150 ml), N-bro-
mosuccinimide (0.15 mol) and benzoyl peroxide
(0.5 g) were added. The reaction mixture was
boiled under reflux for 2 h. The solvent was then
evaporated ”in vacuo“. The residue obtained
(highly lachrymatory) was dissolved in ethanol
(150 ml) and sodium benzenesulfinate (0.1 mol)
was added. The reaction mixture was boiled under
reflux for 2 h, left aside to cool at room tem per-
ature and then poured onto cold water. The solid
product, which formed, was collected by filtration,
washed three times with water, dried and crystal-
lized from the appropriate solvent.
Q 7H 12N202S2 (340.42)
Calcd
Found C 60.2
C 59.98 H 3.55 N 8.23 S 18.84%,
H 3.5 N 8.4 S 18.7%.
2-Amino-4- (p-chlorophenyl)-5-(phenylsulfonyl)-
thiophene-3-carbo-nitrile (7b)
Yield: 61%; m.p. 221 °C (dioxane). - IR: v =
3410, 3318 cm “1(N H 2),2220 c ir r 1(CN), 1636 cm ' 1
(C=C). - ]H NM R (DM SO-d6): 6 = 6.55 (s, 2H,
N H 2), 6.95-7.23 (m, 4H, aromatic-H), 7.53-7.96
(m, 5H, S 0 2Ph).
1,1-Dicyano-2-phenyl-3-(phenylsulfonyl)propene
(3a)
C17H n ClN202S2 (374.87)
Yield: 80%; m.p. 125 °C (ethanol). IR: v = 3010
cm - 1 (CH2), 2220, 2218 cm “1 (2 CN), 1630 cm 1
(C=C). - 'H NM R (CDC13): Ö = 4.25 (s, 2H, CH 2),
6.81-7.20 (m, 5H, aromatic-H), 7.42-7.80 (m, 5H,
S 0 2Ph). - MS (70 eV): m/z (% ): 308 (18) [M+],
Calcd
C 54.46 H 2.95 Cl 9.45 N 7.47 S 17.11 %,
Found C 54.3 H 2.9 Cl 9.3 N 7.4 S 17.0%.
6-Aryl-2-imino-4-phenyl-5-(phenylsulfonyl)-
pyran-3-carbonitriles (10a,b)
C,7H 12N202S (308.36)
Method a: To a solution of 3a (0.005 mol) and
potassium f-butoxide (0.005 mol) in dry dioxane
(15 ml), the appropriate aromatic aldehyde (0.005
mol) was added. The reaction mixture was boiled
under reflux for 2 h, poured onto ice/water and
neu-tralized with dilute hydrochloric acid (pH —
7). The solid product so formed was collected by
filtration, dried and crystallized from the appropri-
ate solvent.
Calcd
Found C 66.4
C 66.22 H 3.92 N 9.09 S 10.39%,
H 3.0 N 9.2 S 10.2%.
2-(p-Chlorophenyl)-l ,1-dicyano-3-
(phenylsulfonyl)propene (3b)
Yield: 80%; m.p. 131 °C (ethanol). - IR: v =
3006 cm - 1 (CH 2), 2222, 2219 cm “1 (2 CN), 1630
cm - 1 (C=C). - 'H NMR (DM SO-d6): <3 = 4.13 (s,
2H, CH2), 6.63-7.10 (m, 4H, aromatic-H), 7.51-
7.90 (m, 5H, S 0 2Ph).
4,6-Diphenyl-2-imino-5-(phenylsulfonyl)pyran-3-
carbonitrile (10a)
C 17H n ClN202S (342.80)
Yield: 45%; m.p. 185 °C (dioxane). - IR: v =
3436 cm " 1 (NH), 2220 cm ' 1 (CN), 1640 cm' 1 (C=
C). - 'H NM R (DM SO-d6): Ö = 6.92-7.80 (m, 15
H, aromatic protons), 12.41 (s, 1H, NH).
Calcd
C 59.56 H 3.23 Cl 10.34 N 8.17 S 9.35%,
Found C 59.4 H 3.2 Cl 10.3 N 8.0 S9.3% .
2-Amino-4-aryl-5-(phenylsulfonyl)thiophene-3-
C24H 16N 203S (412.46)
carbonitriles (7a,b)
Calcd
Found C 70.1
C 69.88 H 3.91 N 6.79 S7.77% ,
H 3.7 N 6.7 S7.8% .
General procedure: To a solution of 3a,b (0.005
mol) in dioxane (20 ml), elemental sulfur (0.005
mol) was added. The reaction mixture was boiled
under reflux for 30 min, left to cool at room tem -
perature and then poured into cold water whereby
the solid product that separated was collected by
filtration and crystallized from the appropriate
solvent.
6-(p-Chlorophenyl) -2-imino-4-phenyl-5-
(phenylsulfonyl)pyran-3-carbonitrile (10b)
Yield: 52%; m.p. 214 °C (dioxane). - IR: v =
3445 cm - 1 (NH), 2222 c n r 1 (CN), 1636 c ir r 1 (C=
C). - ’H NM R (DM SO-d6): Ö = 6.78-7.91 (m,
14H, arom atic-H ),12.71 (s, 1H. NH).
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131
A. W. Erian et al. ■A Novel Synthesis of Sulfone Systems as Antimicrobial Agents
solid product was collected by filtration, washed
several times with boiling ethanol. Yield: 46%;
m.p. 260 °C (DMF). - IR: v = 3400, 3340 cm ' 1
(NH2), 2220 cm “1 (CN), 1695 cm " 1 (CO). - XH
NMR: insoluble in common NM R solvents. - MS
(70 eV): m/z (% ) 544 (26) [M+],
C24H15C1N203S (446.91)
Calcd
C 64.50 H 3.38 CI 7.93 N 6.26 S7.17% ,
Found C 64.3 H 3.3 CI 7.8 N 6.2 S7.0% .
Method b: To a solution of 3a (0.005 mol) in dry
dioxane (15 ml), benzoyl chloride (0.005 mol) was
added. The reaction mixture was boiled under re-
flux for 2 h, stirred overnight at room tem perature
C33H24N20 4S (544.63)
Calcd
C 72.77 H 4.44 N 5.14 S 5.88%,
and then poured onto cold water. The solid pro- Found C 72.9
duct which formed was filtered off, crystallized
H 4.2 N 5.3 S5.9% .
from dioxane (yield 75%) and it was found to be
identical in all aspects (m.p., mixed m.p. and IR
data) with an authentic sample of 10a prepared
according to method (a).
3-Amino-1-aryl-4-benzoyl-5-phenylazo-5-(phenyl-
sulfonyl)cyclopentadiene-2-carbonitriles (14a,b)
General procedure: To a stirred solution of 12a,b
(0.005 mol) in ethanol (50 ml) containing sodium
acetate (4 g), benzene diazonium chloride (0.005
mol)[prepared by adding sodium nitrite (0.005
mol) to aniline (0.005 mol) in concentrated hydro-
chloric acid (2 ml) at 0 -5 °C while stirring] was
added dropwise while cooling at 0 -5 °C and stir-
ring. The reaction mixture was then left at room
tem perature for lh and the solid product which
formed in each case was collected by filtration and
crystallized from the appropriate solvent.
3-Amino-1 -aryl-4-benzoyl-5-(phenylsulfonyl)-
cyclopentadiene-2-carbonitriles (12a,b)
General procedure: To a solution of 3a,b (0.01
mol ) and potassium f-butoxide (0.01 mol) in dry
dioxane (25 m l), phenacyl bromide (0.01 mol) was
added. The reaction mixture was refluxed for 5 h.
The solid product, which formed on dilution with
water and neutralization with dilute HC1 was col-
lected by filtration, dried and crystallized from the
appropriate solvent.
3-Amino-4-benzoyl-l-phenyl-5-phenylazo-5-
(phenylsulfonyl)cyclo-pentadiene-2-carbonitrile
(14a)
3-Amino-4-benzoyl-l -phenyl-5-(phenylsulfonyl) -
cyclopentadiene-2-carbonitrile (12a)
Yield: 54%; m.p. 218 °C (ethanol). - IR: v =
3400, 3330 cm “1(NH2), 2220 c ir r 1(CN), 1695 cm “1
(CO). - !H NM R (CDC13): (5 = 3.91 (s, 2H, N H 2),
6.75-7.80 (m, 20H, aromatic-H).
Yield: 60%; m.p. 130 °C (ethanol). - IR: v =
3400, 3330 cm - 1 (NH2), 2220 (CN), 1695 (CO). -
‘H NMR (DM SO-d6): (3 = 3.92 (s, 2H, N H 2), 4.42
(s, 1H, CH), 6.71-7.80 (m, 15H, aromatic-H).
C31H 22N40 3S (530.60)
C2,H 18N203S (426.87)
Calcd
Found C 70.3
C 70.17 H 4.18 N 10.55 S 6.04%,
H 3.9 N 10.6 S 5.8%.
Clacd
Found C 70.6
C 70.34 H 4.25 N 6.56 S7.60% ,
H 4.2 N 6.6 S 7.2%.
3-Amino-4-benzoyl-l-(p-chlorophenyl)-5-phenyl-
azo-5-(phenyIsulfonyl)cyclopentadiene-2-
carbonitrile (14b)
3-Amino-4-benzoyl-l-(p-chlorophenyl)-5-(phenyl-
sulfonyl)cyclopentadiene-2-carbonitrile (12b)
Yield: 54%; m.p. 142 °C (dioxane). - IR: v =
3415,3326 cm “1(NH2), 2222 cm “1(CN), 1690 cm “ 1
(CO). - !H NM R (DM SO-d6): Ö = 4.12 (s, 2H,
NH2), 4.75 (s, 1H, CH), 6.91-7.92 (m, 14H, aro-
matic-H).
Yield: 58%; m.p. 226 °C (ethanol). - IR: v =
3410, 3337 cm - 1 (NH2), 2218 cm - 1 (CN), 1690
(CO). - 'H NMR (DM SO-d6): (3 = 3.51 (s, 2H,
N H 2), 6.93-7.95 (m, 19H, aromatic-H).
C31H 21C1N40 3S (565.05)
C25H 17C1N203S (461.32)
Calcd
C 65.89 H 3.74 Cl 6.27 N 9.91 S5.67% ,
Calcd
C 65.08 H 3.71 Cl 7.68 N 6.07 S7.03% ,
Found C 65.6 H 3.7 Cl 6.2 N 9.8 S5.6% .
Found C 65.0 H 3.6 Cl 7.4 N 5.9 S 6.8%.
Cycloaddition Reactions of 12a,b with Electron
Poor Olefins
3-Amino-4-benzoyl-5-phenacyl-l-phenyl-5-(phenyl-
sulfonyl)cyclopentadiene-2-carbonitrile (13)
Synthesis of 15a,b and 16a,b
The same experimental procedure described
above for the synthesis of 12 has been followed
except for using phenacyl bromide (0.02 mol). The
General procedure: To a solution of 12a,b (0.005
mol) in dry acetonitrile (10 ml), either dimethyl
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132
A. W. Erian et al. • A Novel Synthesis of Sulfone Systems as Antimicrobial Agents
acetylenedicarboxylate
(0.005 mol) was added. The reaction mixture was
or
tetracyanoethylene
C31H 23C1N20 7S (603.05)
Calcd C 61.74 H 3.84 Cl 5.88 N 4.64 S 5.32%,
boiled under reflux for 15 min, then left aside at Found C 61.5 H 3.8 Cl 5.7 N 4.6 S5.1% .
room tem perature overnight. The solid product
obtained in each case was filtered off and crystal-
lized from the appropriate solvent.
Compound 16a: Yield: 66%; m.p. 215 °C (aceto-
nitrile). - IR: v = 3400, 3260 (N H ,), 2225-2218
cm - 1 (CN), 1670 cm “1 (CO). - 'H NM R (DMSO-
d6): Ö = 4.39 (s, 1H, CH), 6.90-7.80 (m, 15H, aro-
matic-H), 8.91 (br s, 2H, N H 2).
Compound 15a: Yield: 71%; m.p. 156 °C (aceto-
nitrile). - IR: v = 3400, 3290 cm' 1 (NH2), 2219
cm “1 (CN), 1680-1672 cm " 1 (CO), 1620 cm “ 1(C=
C). - lH NM R (CDC13): <5 = 3.70 (s, 3H, CH 3),
3.78 (s, 3H, C H 3), 4.31 (s, 1H, CH), 6.95-7.80 (m,
15H, aromatic-H), 8.10 (br s, 2H, NH 2). - MS (70
eV): m/z (% ) 568 (12) [M+],
C31H 18N60 3S (554.58)
Calcd
Found C 66.9
C 67.14 H 3.27 N 15.15 S5.78% ,
H 3.3 N 15.2 S5.9% .
C3iH 24N20 7S (568.60)
Calcd” C 65.48 H 4.25 N 4.93 S 5.64%,
Compound 16b: Yield: 69%; m.p. 221 °C
(DM F). - IR: v - 3410, 3262 (NH2), 2226-2215
(CN), 1675(CO). - !H NM R (DM SO-d6): (3 = 4.28
(s, 1H, CH), 6.83-7.65 (m, 14H, aromatic-H), 8.57
(br s, 2H, N H 2).
Found C 65.2
H 4.0
N 5.1
S 5.6%.
Compound 15b: Yield: 68%; m.p. 164 °C (etha-
nol). - IR: v = 3406, 3295 cm ' 1 (NH2), 2220 cm " 1
(CN), 1670-1660 cm " 1(CO), 1625 cm “1 (C=C). -
*H NM R (DM SO-d6): Ö = 3.62 (s, 3H, CH3), 3.81
C31H 17C1N60 3S (587.03)
(s, 3H, C H 3), 4.20 (s, 1H, CH), 6.90-7.73 (m, 14H, Calcd
C 63.21 H 2.91 Cl 6.02 N 14.26 S 5.44%,
Found C 63.0 H 2.9 Cl 5.8 N 14.10 S 5.2%.
aromatic-H), 8.53 (br s, 2H, NH 2).
[10] S. M. Sherif, A. W. Erian, Heterocycles 43, 1085
[1] A. K. Mukeriee, R. Ashare, Chem. Rev. 91,
(1991).
[2] J. W. McFarland, Sulfur Rep. 1, 215 (1981).
[3] A. W. Erian, S. M. Sherif, Tetrahedron, in press
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