Cyanoacetanilides intermediates in heterocyclic synthesis. Part 4: Preparation of some hitherto unknown thiazolidine and bisthiazolidine derivatives

Article abstract of DOI:10.1080/10426500701729554

Some novel thiazolidine and bisthiazolidine derivatives were synthesized from the reaction of cyanoacetanilide derivative (2) with isothiocyanates in the presence of potassium hydroxide followed by in situ heterocyclization of the resulting adducts with various α-halogenated reagents. Copyright Taylor & Francis Group, LLC.

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Cyanoacetanilides
Intermediates in Heterocyclic
Synthesis. Part 4:
Preparation of Some Hitherto
Unknown Thiazolidine and
Bisthiazolidine Derivatives
Y. A. Ammar a , M. M. Aly a , A. G. Al-Sehemi b , Y. A.
Mohamed a , M. A. Salem b & M. S. A. El-Gaby c
a Chemistry Department, Faculty of Science , Al-
Azhar University , Nasr City, Cairo, Egypt
b Chemistry Department, Teachers Colleges, at
Abha , King Khalid University , Saudi Arabia
c Chemistry Department, Faculty of Science , Al-
Azhar University at Assiut , Assiut, Egypt
Published online: 24 Jun 2008.
To cite this article: Y. A. Ammar , M. M. Aly , A. G. Al-Sehemi , Y. A. Mohamed , M.
A. Salem & M. S. A. El-Gaby (2008) Cyanoacetanilides Intermediates in Heterocyclic
Synthesis. Part 4: Preparation of Some Hitherto Unknown Thiazolidine and
Bisthiazolidine Derivatives, Phosphorus, Sulfur, and Silicon and the Related Elements,
183:7, 1710-1721, DOI: 10.1080/10426500701729554
To link to this article: http://dx.doi.org/10.1080/10426500701729554
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Phosphorus, Sulfur, and Silicon, 183:1710–1721, 2008
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500701729554
Cyanoacetanilides Intermediates in Heterocyclic
Synthesis. Part 4: Preparation of Some Hitherto
Unknown Thiazolidine and Bisthiazolidine Derivatives
Y. A. Ammar,1 M. M. Aly,1 A. G. Al-Sehemi,2
Y. A. Mohamed,1 M. A. Salem,2 and M. S. A. El-Gaby3
1Chemistry Department, Faculty of Science, Al-Azhar University,
Nasr City, Cairo, Egypt
2Chemistry Department, Teachers Colleges, at Abha, King Khalid
University, Saudi Arabia
3Chemistry Department, Faculty of Science, Al-Azhar University
at Assiut, Assiut, Egypt
Some novel thiazolidine and bisthiazolidine derivatives were synthesized from the
reaction of cyanoacetanilide derivative (2) with isothiocyanates in the presence of
potassium hydroxide followed by in situ heterocyclization of the resulting adducts
with various α-halogenated reagents.
Keywords Bisthiazolidine; thiazolidine; thiophene derivatives
INTRODUCTION
Many thiazolidine derivatives have been demonstrated to pos-
sess antibacterial,1antifungal,2 anticonvulsant,3 anticancer,4 and
antituberculosis5 activities. In addition, thiazolidines have reported
as novel inhibitors of the bacterial enzyme Mur B that was a
precursor acting during the biosynthesis of peptidoglycan.6 Further-
more, antibacterial,7 antifungal,8 insulin releasing,9 carbonic anhy-
drase inhibitory,10 antiinflammtory,11 and antitumor12 properties of
sulfamoyl moiety were described. In view of the above observations and
in continuation of our research program on the chemistry of cyanoac-
etanilide derivatives,13−15 we report herein the synthesis of the versa-
tile hitherto unknown thiazolidine and bisthiazolidine derivatives hav-
ing an sulfamoyl moiety from the readily accessible cyano-acetanilide
derivative (2).
Received 29 May 2007; accepted 1 September 2007.
Dedicated to Professor A. M. Sh. El-Sharief on the occasion of his 60th birthday.
Address correspondence to M. S. A. El-Gaby, Chemistry Department, Faculty of Sci-
ence, Al-Azhar University at Assiut, Assiut 71524, Egypt. E-mail: m elgaby@hotmail.com
1710

Thiazolidine Derivatives
1711
RESULTS AND DISCUSSION
In the present contribution, we investigated the reaction of cyanoac-
etanilide derivative (2) with isothiocyanates in the presence of potas-
sium hydroxide followed by in situ heterocyclization of the resulting
adducts with various α-halogenated compounds. The required start-
ing material cyanoaceto-4-sulfamoylanilide (2) was synthesized in good
yield (92%) through the reaction of sulfanilamide (1) with ethyl cyanoac-
etate in refluxing m-xylene (Scheme 1).
NH2
NHCOCH2CN
CN
CH2COOC2H5
m-xylene/reflux
SO2NH2
SO2NH2
(1)
(2)
SCHEME 1
The non-isolable potassium sulfide salt (3) was achieved by the nu-
cleophilic addition of active methylene group in compound (2) to phenyl
isothiocyanate in dry dimethylformamide at room temperature in the
presence of potassium hydroxide (Scheme 2). The potassium salt (3) was
exploited to synthesize some new thiazolidine derivatives. Treatment
of intermediate (3) with bromomalononitrile (4a) at room temperature
O
Cl
O
4b
O
S
O
S
PhN=C=S
CN
CH2CN
CN
S
(2)
N
H
H2N
H2N
N
DMF/KOH
(-KCl)
H
O
O
PhNH
SH K
Ph
N
(3)
H2N
Br
(7)
4a
CH(CN)2
(-KBr)
O
O
N
O
S
O
CN
S
CN
S
H2N
N
H
H2N
S
N
H
O
O
Ph
N
Ph
H
HN
(5)
CN
H2N
(6)
CN
SCHEME 2

1712
Y. A. Ammar et al.
gave iminothiazolidine derivative 5 in high yield (86%). The structure
of the isolated product was confirmed based on elemental analysis and
spectral data. Its infrared spectrum showed a strong absorption band
at 2194 cm−1 due to C N group in addition to the absorption bands
characteristic for NH and C O (amide) functional groups. Structure
1
(6) was ruled out based on the HNMR spectrum of the reaction prod-
uct, which revealed a signal a δ 7.27 ppm for a methine proton in ad-
dition to the presence of two NH and aromatic protons. Formation of
(5) was assumed to proceed via the initial alkylation followed by in
situ heterocyclization16 through nucleophilic addition of the secondary
amino group to one of the two cyano groups. Cycloalkylation of the in-
termediate (3) with chloroaceto-nitrile (4b) afforded the novel aminoth-
iazolidine derivative (7) in acceptable yield (72%). The molecular struc-
ture of (7) was established based on analytical and spectral data. Its
1HNMR spectrum in DMSO-d6 was characteristic by the presence of a
singlet at δ 6.90 ppm due to the thiazole-H. The reaction mechanism was
assumed to proceed through initial alkylation followed by the addition
of the secondary amino group to the cyano group and tautomerization
to yield the cyclized product (7), (Scheme 2).
Cyclocondensation of the intermediate salt (3) with chloro-
acetone (8a) at room temperature afforded the corresponding 2,3-
dihydrothiazole derivative (9). The other possible structure (10; R =
CH3) was ruled out based on elemental analysis and spectral data.
The infrared spectrum of compound (9) showed the characteristic ab-
sorption band at 2170 cm−1 for the C≡N functional group. The mass
spectrum of compound (9; C19H16N4O3S2) showed a molecular ion peak
at m/z = 412 and the base peak was found in the spectrum at m/z = 214.
The structure (9) resulting from the initial alkylation followed by in-
tramolecular cyclization through dehydration to form (9). On the other
hand, treatment of (3) with phenacyl bromide (8b) gave the thioether
derivative (11; R = C6H5), by elimination of potassium bromide. The
structure of thioether (11) was confirmed by examining spectral data.
Its infrared spectrum indicated the presence of the C≡N and C O ab-
sorption bands. In addition the structure (11) was supported by 1HNMR
spectrum which revealed a singlet at δ = 4.01 ppm assigned to the
methylene moiety. Cyclization of (11) by refluxing in ethanol in the
presence of piperidine gave the novel aminothiophene derivative (10;
R = C6H5), via Thorpe-Ziegler reaction.17 the structure of compound
(10; R = C6H5) was confirmed by its infrared spectrum which indicated
the absence of C≡N absorption band and contain the characteristic ab-
sorption bands for NH2 and C O functional groups. The formation of
compound (10) was assumed to proceed via nucleophilic attack of active
methylene to the cyano group and tautomerization17 (Scheme 3).

Thiazolidine Derivatives
1713
O
O
(i) -KCl
CN
S
H2N S
N
(ii) -H2O
O
H
Ph N
H3C
O
(8a)
(9)
O
H2N S
O
NH2
O
N
H
PhNH
R C CH2X (8a,b)
(3)
S
COR
(10)
EtOH/piperidine
reflux
O
O
(8b)
(-KBr)
CN
H2N S
O
N
H
R
O
PhNH
S
(11)
8a; R = CH3, X = Cl
8b; R = C6H5, X = Br
10 and 11; R = C6H5
SCHEME 3
Our investigation was also extended to study the reaction of inter-
mediate salt (3) with chloroacetic acids (12a,b). thus, the reaction of
(3) with α-chloroacetic acid (12a) and ethyl chloroacetate (12b) at room
temperature gave the acyclic products (13a) and (13b), respectively; via
loss of potassium chloride. The infrared spectra of compounds (13a,b)
indicated the presence of the C≡N and C O functional groups. Thiazo-
lidine derivative (14) was obtained by cyclization of (13a) in refluxing
ethanol in the presence of piperidine, through dehydration of water. In
the mass spectrum of compound (14; C18H14N4O4S2) a molecular ion
peak was found at m/z = 414 (23.20), and the base peak was observed
in the spectrum at m/z = 215. On the other hand, refluxing of (13b) in
ethanolic solution containing a few drops of piperidine as basic catalyst
afforded the novel thiazolidinone (15), through elimination of ethanol
with partial hydrolysis of cyano group. When intermediate salt (3) was
treated with N-(4-methoxy-phenyl)chloroacetamide (16) at room tem-
perature, thiophene derivative (17) was formed smoothly. The structure

1714
Y. A. Ammar et al.
of compound (17) was confirmed by its infrared spectrum, which exhib-
ited the disappearance of absorption band for C N group. Compound
(17) was assumed to be formed via initial alkylation followed by in-
tramolecular cyclization through Thorpe-Ziegler reaction17 (Scheme 4).
SCHEME 4
The present contribution was extended to synthesize hitherto
unknown bisthiazolidinone derivatives from 1,4-phenylenediisothio-
cyanate (18) and cyanoacetanilide (2). The reaction of 1,4-phenylenedi-
isothiocyanate (18) with cyanoacetanilide in the presence of potas-
sium hydroxide at room temperature gave the non-isolated adduct (19)

Thiazolidine Derivatives
1715
SCHEME 5
(Scheme 5). The latter was converted into bisthiazolidinone deriva-
tive (20) by treatment with chloroacetone (8a) at room temperature,
through initial alkylation and elimination of water. Also, cyclization
of the adduct (19) with ethyl chloroacetate (12b) afforded the corre-
sponding bis(thiazolidinone) derivative (21), via initial alkylation and
elimination of ethanol. The mass spectrum of compound (20) exhibited a
molecular ion peak at m/z = 750 (3.23%) corresponding to the molecular
formula C30H22N8O8S4 with base peak at m/z = 63.

1716
Y. A. Ammar et al.
Refluxing of cyanoacetanilide derivative (2) with sulfanylacetic acid
(22) in glacial acetic acid furnished thiazolidinone derivative (23)
based on its analytical and spectral data. Its infrared spectrum re-
vealed characteristic absorption band for C O (thiazolidinone) func-
1
tional group. The H NMR spectrum of the reaction product recorded
in DMSO-d6 displayed a signal at δ = 5.85 ppm for a methylidene-
H in addition to the presence of methylene, two NH, NH2 and aro-
matic protons. Formation of thiazolidinone (23) is assumed to pro-
ceed via initial nucleophilic addition of mercapto group to cyano group
followed by intramolecular cyclization through elimination of water
to yield (23). Condensation of compound (23) with aromatic alde-
hyde in refluxing ethanol in the presence of piperidine yielded the
novel 5-arylmethylidene-2-[N-(4-sulfamoylphenyl)acteamide-2-yl]-4,5-
dihydro-4-thiazolidinones (24a,b). Bisthiazolidinone derivative (26)
was achieved by refluxing of compound (23) with terephthalaldehyde
(25) in ethanol at reflux temperature in the presence of piperidine
(Scheme 6).
SCHEME 6

Thiazolidine Derivatives
1717
CONCLUSIONS
In conclusion, the non-isolable intermediate (3) was exploited to syn-
thesize some novel thiazolidine derivatives via its reaction with α-halo
compounds. In addition, bisthiazolidine derivatives were prepared by
various methods.
EXPERIMENTAL
All melting points are uncorrected. IR spectra (KBr) were measured on
Shimadzu 440 spectrometer, 1H NMR spectra were obtained in DMSO
on a Varian Gemini 200 MHz spectrometer using TMS as internal stan-
dard; chemical shifts are reported as (ppm). Mass spectra were obtained
on GCMS\QP 1000 Ex mass spectrometer at 70 eV. Elemental analy-
ses were carried out at the Microanalytical Center, Faculty of Science
(Cairo University, Egypt). The characteristics data for prepared com-
pounds are given in Table I. Also the spectral data are collected in
Table II.
Preparation of Cyanoaceto-4-sulfamoylanilide (2)
A mixture of sulfanilamide 1 (0.01 mol) and ethyl cyanoacetate (0.01
mol) in m-xylene (30 mL) was refluxed for 4 h, the solid product which
produced on heating was collected and crystallized from dioxane as
colorless crystals, m.p. 230◦C (lit. m.p. 228◦C).18
Preparation of Compounds (5) (R = CN), (7), (9), (11), (13a; R =
H), (13b; R = C2H5), (17), (20), and (21)—General Procedure
To suspension of finely powdered potassium hydroxide (0.01 mol) in dry
dimethylformamide (10 mL) at 0◦C the anilide (2, 0.01 mol) and then
the isothiocyanate (0.01 mol) were added in portions. The reaction mix-
ture was stirred at room temperature for 3 h and then treated with
α-halogenated compound (0.01 mol) and left at room temperature for
24 h; then it was poured into ice/water and acidified with 0.1 N HCl at
pH 3-4. The resulting precipitate was filtered off, dried, and recrystal-
lized from the proper solvent.
Formation of Compounds 10, 14, and 15—General Procedure
A mixture of compound 11, 13a, or 13b (0.01 mol) and piperidine
(0.01 mol) in ethanol (30 mL) was heated under reflux for 1 h, the solid

1718
Y. A. Ammar et al.
TABLE I Characteristics Data for the Synthesized Compounds
Elemental analyses
calcd./found (%)
Compd. Yield
Solvent
cryst.
M.p.
(◦C)
Molecular formula
(mol. wt.)
no.
(%)
C%
H%
N%
5
86
Benzene
Benzene
AcOH
230–232
240–241
260–262
>300
C19H14N6O3S2
(438)
C18H15N5O3S2
(413)
52.05 3.19 19.17
52.10 3.10 19.10
52.30 3.63 16.94
52.25 3.70 16.90
55.23 3.88 13.59
55.10 3.80 13.50
58.53 4.06 11.38
58.40 4.00 11.30
58.53 4.06 11.38
58.40 4.00 11.30
50.00 3.70 13.96
50.10 3.80 12.90
52.17 4.34 12.17
52.20 4.30 12.10
52.17 3.38 13.52
52.10 3.30 13.60
50.00 3.70 12.96
50.00 3.60 12.90
55.86 4.28 13.03
55.70 4.20 13.10
48.00 2.93 14.93
48.10 2.90 15.00
51.47 3.48 15.01
51.40 3.40 15.10
42.17 3.51 13.41
42.10 3.40 13.30
54.93 4.09 10.12
54.80 4.10 10.12
7
72
60
65
75
75
80
63
50
70
60
70
80
50
60
70
9
C
C
C
C
19H16N4O3S2
(412)
24H20N4O4S2
(492)
24H20N4O4S2
(492)
18H16N4O5S2
(432)
10
AcOH
11
Benzene
Benzene
Benzene
AcOH
190–191
150–152
90–91
13a
13b
14
C20H20N4O5S2
(460)
230–231
70–72
C
18H14N4O4S2
(414)
15
AcOH
C
18H16N4O5S2
(432)
17
AcOH
260–261
C25H23N5O5S2
(537)
20
EtOH/DMF 250–251
C
30H22N8O8S4
(750)
21
EtOH/DMF
AcOH
>300
240–241
250–251
278–279
>300
C32H26N8O6S4
(746)
23
C
11H11N3O4S2
(313)
24a
24b
26
AcOH
C19H17N3O4S2
(415)
AcOH
C
18H14ClN3O4S2
(435.5)
49.39 3.21
49.20 3.10
9.64
9.50
EtOH/DMF
C
30H24N6O8S4
(724)
49.72 3.31 11.60
49.60 3.20 11.70
product which produced on heating was collected and recrystallized
from the proper solvent to give 10, 14, and 15, respectively.
Synthesis of 2-[N-(sulfamoylphenyl)acetamide-2-yl]-4,5-
dihydro-4-thiazolidinone (23)
A mixture of compound 2 (0.01 mol) and sulfanylacetic acid 22
(0.01 mol) in glacial acetic acid (10 mL) was heated under reflux for
3 h, then allowed to cool and poured into water (50 mL). The solid prod-
uct was collected and recrystallized to give 23.

Thiazolidine Derivatives
1719
TABLE II Spectral Data of the Synthesized Compounds
IR/ν
(cm−1
)
1H NMR (DMSO-d6) (δ/ppm)
max
5
7
9
3336, 3262 (NH2), 2194
(C N), 1656 (C O;
amide).
3351, 3229 (NH2), 1645
(C O; amide).
6.50 (s, 2H, SO2NH2; exchangeable), 7.01 (s,
1H, thiazole-H), 7.27–7.75 (m, 10H, Ar-H +
NH), 10.2 (s, 1H, NH; exchangeable).
6.60 (s, 2H, NH2; exchangeable), 6.90 (s, 1H,
thiazole-H), 7.26–7.78 (m, 11H, Ar-H+ NH2),
9.80 (s, 1H, NH; exchangeable).
1.87 (s, 3H, CH3), 6.99 (s, 1H, thiazole-H), 7.23
(s, 2H, SO2NH2; exchangeable), 7.52–7.77
(m, 9H, Ar-H), 9.08 (s, H, NH; exchangeable).
3400, 3284 (NH2), 2170
(C N), 1624 (C O;
amide).
10 3416, 3342, 3264 (NH/NH2), 7.16-7.81 (m, 16H, Ar-H+NH2), 8.16, 8.40 (2s,
1662 (C O; benzoyl).
2H, 2NH; exchangeable), 9.45 (2H, NH2;
exchangeable).
11 3280, 3256 (NH2), 2198
(C N), 1686 (C O;
amide), 1656 (C O;
benzoyl)..
4.01 (s, 2H, SCH2), 7.22–8.03 (m, 16H, Ar-H +
NH2), 9.85, 10.21 (2s, 2H, 2NH;
exchangeable).
13a 3432 (OH), 2190 (C N),
1720 (C O).
4.1 (s, 2H, SCH2), 7.39-7.80 (m, 11H, Ar-H +
SO2NH2), 9.79, 10.67 (2s, 2H, 2NH;
exchange-able), 11.97 (s, H, OH;
exchangeable).
13b 3300, 3256 (NH2), 2926
(CH-aliph.), 2198 (C N),
1734 (C O; ester), 1654
(C O; amide).
1.20 (t, 3H, CH3), 2.90 (s, 2H, SCH2), 4.21 (q,
2H, CH2), 7.29–7.96 (m, 11H, Ar-H +
SO2NH2), 9.7, 10.11 (2s, 2H, 2NH;
exchangeable).
14 3384, 3278 (NH2), 2190
(C N), 1718 (C O;
6.05 (s, 1H, thiazolidinone-H), 7.21 (s, 2H,
SO2NH2; exchangeable), 7.67–7.79 (m, 9H,
Ar-H), 10.49 (s, 1H, NH; exchangeable), 12.30
(s, 1H, OH; exchangeable).
thiazolidinone), 1660
(C O; amide).
15 3440, 3338 (NH2), 1648
(C O; amide).
3.65 (s, 2H, NH2; exchangeable), 4.01 (s, 2H,
SCH2), 6.75 (s, 2H, NH2; exchangeable),
7.21–7.79 (m, 9H, Ar-H), 12.2 (s, 1H, NH;
exchangeable),
17 3402, 3260 (NH2), 2928
(CH-aliph.), 1664 (C O;
amide).
20 3330, 3256 (NH2), 2198
(C N), 1734 (C O; ester),
1684 (C O; amide).
21 3346, 3108 (NH2), 2182
(C N), 1640 (C O;
amide).
3.73 (s, 3H, OCH3), 5.11 (s, 1H, thiophene-H),
6.90–7.79 (m, 15H, Ar-H+ NH2), 8.92, 9.35,
10.26, 12.21 (4s, 4H, 4NH; exchangeable),
4.02, 4.17 (2s, 4H, 2SCH2), 7.28–7.79 (m, 16H,
Ar-H + 2SO2NH2), 9.78, 10.26 (2s, 2H, 2NH;
exchangeable),
2.03 (s, 6H, 2CH3), 7.02 (s, 2H, thiazolidine),
7.22 (s, 4H, 2SO2NH2; exchangeable),
7.72–7.84 (m, 12H, Ar-H), 9.12 (s, 2H, 2NH;
exchangeable).
23 3320, 3180, 3110 (NH/ NH2), 3.74 (s, 2H, SCH2), 5.85 (s, 1H, methylidene-H),
1708 (C O;
thiazolidinone), 1660
(C O; amide).
7.23 (s, 2H, SO2NH2; exchangeable), 7.76 (m,
4H, Ar-H), 10.18, 11.83 (2s, 2H, 2NH;
exchangeable).
(Continued on next page)

1720
Y. A. Ammar et al.
TABLE II Spectral Data of the Synthesized Compounds
(Continued)
IR/ν
(cm−1
)
1H NMR (DMSO-d6) (δ/ppm)
max
24a 3344, 3252 (NH2), 1684
(C O; thiazolidinone),
1640 (C O; amide).
2.09 (s, 3H, CH3), 6.03 (s, 1H, methylidene-H),
7.25-7.84 (m, 11H, Ar-H + SO2NH2+
methylidene-H), 10.40, 12.24 (2s, 2H, 2NH;
exchangeable).
24b 3332, 3240 (NH2), 1686
(C O; thiazolidinone),
1660 (C O; amide).
6.05 (s, 1H, methylidene-H), 7.25 (s, 2H,
SO2NH2; exchangeable), 7.51–7.79 (m, 9H,
Ar-H + benzylidene-H), 10.47, 12.30 (2s, 2H,
2NH; exchangeable).
26 3436, 3400 (NH2), 1686
(C O; thiazolidinone),
1654 (C O; amide).
6.10 (s, 2H, methylidene-H), 7.20–2.8 (m, 18H,
Ar-H + 2SO2NH2+ benzylidene-H), 10.1,
10.42 (2s, 2H, 2NH; exchangeable).
Formation of Compounds (24a,b) and 26—General Procedure
A mixture of compound 23 (0.01 mol), aromatic aldehyde or terephtha-
laldehyde 25 (0.01 mol) and piperidine (0.01 mol) in ethanol (40 mL)
was heated under reflux for 3 h, the solid product, which was pro-
duced on heating, was collected and recrystallized to give 24a,b and 26,
respectively.
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