Preparation of novel 2-(2-oxo-2 H-chromen-4-yl)-3-arylthiazolidin-4-one derivatives using an efficient ionic liquid catalyst

Article abstract of DOI:10.1080/17415993.2015.1089440

An eco-friendly procedure for synthesis of 2-(2-oxo-2H-chromen-4-yl)-3-arylthiazolidin-4-one derivatives by three-component reaction of 2-oxo-2H-chromene-4-carbaldehydes, aromatic amines and thioglycolic acid, with tetramethylbutane-1,4-diammonium acetate

Full text of DOI:10.1080/17415993.2015.1089440

Journal of Sulfur Chemistry
ISSN: 1741-5993 (Print) 1741-6000 (Online) Journal homepage: http://www.tandfonline.com/loi/gsrp20
Preparation of novel 2-(2-oxo-2H-chromen-4-yl)-3-
arylthiazolidin-4-one derivatives using an efficient
ionic liquid catalyst
Majid Ghashang, Hadi Taghrir, Mohammad Najafi Biregan, Negar Heydari &
Fateme Azimi
To cite this article: Majid Ghashang, Hadi Taghrir, Mohammad Najafi Biregan, Negar Heydari
& Fateme Azimi (2015): Preparation of novel 2-(2-oxo-2H-chromen-4-yl)-3- arylthiazolidin-4-
one derivatives using an efficient ionic liquid catalyst, Journal of Sulfur Chemistry, DOI:
10.1080/17415993.2015.1089440
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Date: 02 November 2015, At: 22:46

JOURNAL OF SULFUR CHEMISTRY, 2015
http://dx.doi.org/10.1080/17415993.2015.1089440
Preparation of novel 2-(2-oxo-2H-chromen-4-yl)-3-
arylthiazolidin-4-one derivatives using an efficient ionic
liquid catalyst
Majid Ghashang, Hadi Taghrir, Mohammad Najafi Biregan, Negar Heydari and Fateme
Azimi
Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Iran
ABSTRACT
ARTICLE HISTORY
Received 14 July 2015
Accepted 29 August 2015
An eco-friendly procedure for synthesis of 2-(2-oxo-2H-chromen-4-
yl)-3-arylthiazolidin-4-one derivatives by three-component reaction
of 2-oxo-2H-chromene-4-carbaldehydes, aromatic amines and thio-
glycolic acid, with tetramethylbutane-1,4-diammonium acetate as a
low-cost ionic liquid catalyst under reflux condition is described. The
use of an ionic liquid as a catalyst has the advantages of high yields,
short reaction time and environmentally friendly reaction media.
KEYWORDS
Thioglycolic acid;
thiazolidin-4-one;
tetramethylbutane-1;
4-diammonium acetate;
2-(2-oxo-2H-chromen-4-yl)-
3-arylthiazolidin-4-one; ionic
liquid
1. Introduction
Heterocyclic compounds containing both nitrogen and sulfur atoms have attracted grow-
ing interest owing to their important medicinal activities. The chemistry of these com-
pounds have been under extensive investigation for decades due to their wide applications
in organic and medicinal chemistry.[1] Among the heterocycles of interest thiazolidin-
4-ones are an important class since they closely resemble other important compounds
with nitrogen and sulfur atoms. This nucleus is associated with diverse anticancer,[2] anti-
HIV,[3,4,5] antimalarial,[6] tuberculostatic,[7] antihistaminic,[8] anticonvulsunt,[9,10]
antibacterial,[11] and antiarrythmic[12] biological activity.
The cyclo-condensation reaction of aldehydes, amines and thioglycolic acid is the main
synthetic route to thiazolidin-4-one derivatives. This condensation is commonly con-
ducted using promoters such as N,Nꢀ-dicyclohexylcarbodiimide which involves a tedious
CONTACT Majid Ghashang
ghashangmajid@gmail.com
© 2015 Taylor & Francis

2
M. GHASHANG ET AL.
Scheme 1. Preparation of 2-(2-oxo-2H-chromen-4-yl)-3-arylthiazolidin-4-one derivatives.
work-up due to the formation of N,N’-dicyclohexyl urea as by-product,[13] and separation
of ferrite,[14] ZnCl2,[15] sodium sulfate,[16] [bmim][PF6],[17,18] activated fly ash,[19]
Saccharomyces cerevisiae [20] and Bi(SCH2COOH)3.[21] Some of these methods have cer-
tain limitations, such as harsh reaction conditions, prolonged heating and the need for
inert and dry atmosphere. These procedures have advantages such as good to excellent
yields; however, the discovery of new synthetic methodologies to facilitate the preparation
of organic compounds is perhaps the most important aspect of this new reaction and is
consequently a central research activity in modern organic chemistry.
In continuing our studies to explore the preparation of heterocyclic compounds,[22–27]
herein, we report a cyclo-condensation reaction of 2-oxo-2H-chromene-4-carbaldehydes,
aromatic amines and thioglycolic acid in the presence of tetramethylbutane-1,4-
diammonium acetate as a catalyst to give a variety of thiazolidin-4-one derivatives
(Scheme 1).
2. Results and discussion
The reaction of 2-oxo-2H-chromene-4-carbaldehyde, 4-methyl aniline and thioglycolic
acid in the presence of tetramethylbutane-1,4-diammonium acetate under several con-
ditions was selected as the model to optimize the reaction conditions (Table 1). Upon
treatment of starting materials as well as a catalyst in nonpolar solvents and Et2O the
desired product 2b was not obtained (Table 1, Entries 1–3). When the reaction was carried
out in polar solvents the reaction has a yield from 31% to 64% (Table 1, Entries 4,5,7). No
formation of 2b was taking place in a solvent-free condition (Table 1, Entry 8). Employing
toluene as the solvent resulted in higher yield of product (Table 1, Entry 6).
Next, to find the optimized amount of tetramethylbutane-1,4-diammonium acetate, the
reaction was carried out by varying the amount of the catalyst (Table 1, Entries 9–12).
Maximum yield was obtained when 0.5 mmol of catalyst was used (Table 1, Entry 10). A
further increase in the amount of catalyst did not have any significant effect on the product
yield. Under the standard conditions, no reaction was observed in the absence of a catalyst.
This shows that the catalyst is essential for the product formation (Table 1, Entry 13).
Under the same reaction conditions a variety of Brønsted acid catalysts were employed
to be compared with the results obtained by tetramethylbutane-1,4-diammonium acetate.

JOURNAL OF SULFUR CHEMISTRY
3
Table 1. Optimization of the reaction conditions in the synthesis of 2-(2-oxo-2H-chromen-4-yl)-3-p-
tolylthiazolidin- 4-one.
Entry
Catalyst (mmol)
T (°C)
Solvent (5 mL)
Time (h)
Yield (%)a
1
2
3
4
5
6
7
8
A (0.25)
A (0.25)
A (0.25)
A (0.25)
A (0.25)
A (0.25)
A (0.25)
A (0.25)
A (1)
A (0.5)
A (0.1)
A (0.05)
–
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
80
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
n-Hexane
CH2Cl2
Et2O
EtOAc
EtOH
Toluene
CH3CN
–
Toluene
Toluene
Toluene
Toluene
Toluene
Toluene
Toluene
Toluene
Toluene
Toluene
10
10
10
10
10
10
10
5
–
–
–
31
45
80
64
25
82
88
63
39
–
48
55
49
32
69
9
6
8
10
11
12
13
14
15
16
17
18
15
15
10
10
10
10
10
10
SiO2-H2SO4 (0.25 mmol H+)
SiO2-HClO4 (0.25 mmol H+)
H2SO4 (0.25 mmol)
HCl (0.25)
CH3COOH (0.25)
aIsolated Yields; A: tetramethylbutane-1,4-diammonium acetate; based on 2-oxo-2H-chromene-4-carbaldehyde (1 mmol),
4-methyl aniline (1 mmol) and thioglycolic acid (1 mmol).
The obtained results indicated that tetramethylbutane-1,4-diammonium acetate is more
effective in comparison with other acid catalysts (Table 1, Entries 14–18).
Having established the optimum reaction conditions, the scope and limitations of this
study were investigated for the synthesis of 2-(2-oxo-2H-chromen-4-yl)-3-arylthiazolidin-
4-one derivatives (Scheme 1, Table 2). As expected, this reaction proceeded smoothly and
the desired products were obtained in good yields. In general, 2-oxo-2H-chromene-4-
carbaldehydes and aromatic amines were well tolerated in this reaction system (Table 2,
product 2a–2l). However, this method is not applicable to aromatic amines containing
electron-withdrawing groups (Table 2, Entry 13).
Encouraged by the above results, we next investigated the reaction of various aromatic
aldehydes under the optimized reaction conditions established for 2-oxo-2H-chromene-
4-carbaldehyde (Scheme 2), and the results are listed in Table 3. In general, the reaction
Table 2. Synthesis of 2-(2-oxo-2H-chromen-4-yl)-3-arylthiazolidin-4-one derivatives using
tetramethylbutane-1,4-diammonium acetate as a catalyst (Scheme 1).
Entry
Aldehyde
Amine
Aniline
4-Methylaniline
4-Methoxyaniline
4-Chloroaniline
Aniline
4-Methylaniline
4-Methoxyaniline
4-Chloroaniline
Aniline
4-Methylaniline
4-Methoxyaniline
4-Chloroaniline
4-Nitroaniline
Product
Time (h)
Yield (%)a
1
2
3
4
5
6
7
8
2-oxo-2H-chromene-4-carbaldehyde
2-oxo-2H-chromene-4-carbaldehyde
2-oxo-2H-chromene-4-carbaldehyde
2-oxo-2H-chromene-4-carbaldehyde
6-chloro-2-oxo-2H-chromene-4-carbaldehyde
6-chloro-2-oxo-2H-chromene-4-carbaldehyde
6-chloro-2-oxo-2H-chromene-4-carbaldehyde
6-chloro-2-oxo-2H-chromene-4-carbaldehyde
5-hydroxy-2-oxo-2H-chromene-4-carbaldehyde
5-hydroxy-2-oxo-2H-chromene-4-carbaldehyde
5-hydroxy-2-oxo-2H-chromene-4-carbaldehyde
5-hydroxy-2-oxo-2H-chromene-4-carbaldehyde
5-hydroxy-2-oxo-2H-chromene-4-carbaldehyde
2a
2b
2c
2d
2e
2f
2g
2h
2i
8
8
8
10
12
12
12
15
8
8
8
10
10
85
88
90
78
86
92
95
80
85
93
91
77
–
9
10
11
12
13
2j
2k
2l
2m
aIsolated yields. All products were characterized by NMR spectra and CHN analysis.

4
M. GHASHANG ET AL.
Scheme 2. Preparation of 2,3-diarylthiazolidin-4-one derivatives.
Table 3. Synthesis of 2,3-diarylthiazolidin-4-one derivatives using tetramethylbutane-1,4-
diammonium acetate as catalyst.
Entry
Aldehyde
Benzaldehyde
4-Methylbenzaldehyde
4-Methoxybenzaldehyde
4-Chlorobenzaldehyde
Benzaldehyde
4-Methylbenzaldehyde
4-Methoxybenzaldehyde
4-Chlorobenzaldehyde
2-Methylbenzaldehyde
2-Chlorobenzaldehyde
3-Nitrobenzaldehyde
Butyraldehyde
Amine
Aniline
Aniline
Aniline
Product
Time (h)
Yield (%)a
1
2
3
4
5
6
7
8
3a
3b
3c
3d
3e
3f
3g
3h
3i
4
3
3
4
3
3
3
3.5
4
85
89
86
80
79
85
88
81
70
73
65
–
Aniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
9
10
11
12
3j
3k
3l
4
5
5
aIsolated yields. All products were purified using plate chromatography (hexane/ethyl acetate 9/1) and characterized by
1H-NMR spectra.
proceeded well with aromatic aldehydes having electron-withdrawing, electron-donating
and halogen substituents (Table 3, Entries 1–11). It was observed that the scope of the
reaction is limited to aromatic aldehydes and the reaction did not proceed when aliphatic
aldehyde were used (Table 3, Entry 12). In the case of aryl aldehydes having electron-
donating groups such as CH3, OCH3 (Table 3, Entries 2,3,6,7), the yield of the corre-
sponding products is higher than that of electron-withdrawing groups (Table 3, Entry 11).
Furthermore, electron-donating substituents on the aromatic ring both in aldehydes and
amines increased the rate of the reaction (Table 3).
The work-up procedure is very clear-cut; that is, the products were isolated and purified
by simple filtration and recrystallization from ethanol. All the synthesized compounds were
confirmed by their 1H and 13C-NMR spectral data and elemental analysis.
In summary, an efficient protocol was described for the preparation of 2-(2-oxo-2H-
chromen-4-yl)-3-arylthiazolidin-4-one derivatives. In the presence of tetramethylbutane-
1,4-diammonium acetate the reactions were carried out in short reaction times with good
yields of the corresponding products. This procedure was also successfully applied to the
synthesis of 2,3-diarylthiazolidin-4-one derivatives in good yields. The present methodol-
ogy has several advantages, including good yields, simple procedure, short reaction times
and mild reaction conditions.

JOURNAL OF SULFUR CHEMISTRY
5
3. Experimental
3.1. Reagents and instrumentation
All reagents were purchased from Merck and Aldrich and used without further purifi-
cation. All yields refer to isolated products after purification. The NMR spectra were
recorded on a Bruker Avance DPX 400 MHz instrument. The spectra were measured
in CDCl3 relative to TMS (0.00 ppm). Elemental analysis was performed on a Her-
aeus CHN-O-Rapid analyzer. TLC was performed on silica gel polygram SIL G/UV
254 plates. Tetramethylbutane-1,4-diammonium acetate can be easily prepared follow-
ing the procedure reported by Alvarez et al.[28] The synthetic strategy prefparation of
2-oxo-2H-chromene-4-carbaldehyde derivatives is depicted in [29].
3.2. General procedure
To a mixture of aldehyde (1 mmol), aromatic amine (1 mmol) and thioglycolic acid
(1 mmol) in toluene (10 mL) was added tetramethylbutane-1,4-diammonium acetate
(0.5 mmol) and the mixture was stirred at reflux condition for the appropriate time
(Tables 2 and 3). The progress of the reaction was monitored by TLC. Upon completion,
the solvent was concentrated and the reaction mixture was recrystallized from ethanol to
afford the pure product.
3.3. Selected data
2-(2-oxo-2H-chromen-4-yl)-3-phenylthiazolidin-4-one (Table 2, Product 2a): 1H-NMR
(400 MHz, CDCl3): 3.72 (d, J = 12.4 Hz, 1H), 3.89 (d, J = 12.4 Hz, 1H), 5.90–5.93 (m,
2H), 7.18–7.42 (m, 8H), 7.73 (t, J = 8.1 Hz, 1H) ppm; 13C NMR (100 MHz, CDCl3):
δ = 34.6, 66.8, 115.9, 118.1, 118.9, 122.8, 123.2, 125.2, 126.6, 129.4, 129.7, 131.6, 145.6,
153.9, 160.5, 172.1 ppm; Found: C, 66.99; H, 4.23; N, 4.51 C18H13NO3S; requires: C, 66.86;
H, 4.05; N, 4.33%].
1
2-(2-oxo-2H-chromen-4-yl)-3-p-tolylthiazolidin-4-one (Table 2, Product 2b): H-NMR
(400 MHz, CDCl3): 2.23 (s, 3H, CH3), 3.71 (d, J = 12.4 Hz, 1H), 3.88 (d, J = 12.4 Hz,
1H), 5.92 (s, 1H), 5.97 (s, 1H, CH), 7.10 (d, J = 7.9 Hz, 1H), 7.39–7.43 (m, 5H), 7.74
(t, J = 8.0 Hz, 1H) ppm; 13C NMR (100 MHz, CDCl3): δ = 21.4, 34.7, 66.9, 114.6, 115.8,
118.0, 119.3, 122.7, 126.5, 129.3, 130.1, 131.7, 132.8, 144.7, 153.9, 160.2, 172.3 ppm; Found:
C, 67.77; H, 4.57; N, 4.27 C19H15NO3S; requires: C, 67.64; H, 4.48; N, 4.15%].
3-(4-methoxyphenyl)-2-(2-oxo-2H-chromen-4-yl)thiazolidin-4-one (Table 2, Product
1
2c): H-NMR (400 MHz, CDCl3): 3.74–3.76 (m, 4H), 3.89 (d, J = 12.4 Hz, 1H), 5.93
(s, 1H), 6.07 (s, 1H, CH), 6.65 (d, J = 7.8 Hz, 1H), 7.21 (d, J = 7.8 Hz, 1H), 7.39–7.43
(m, 3H), 7.73 (t, J = 8.1 Hz, 1H) ppm; 13C NMR (100 MHz, CDCl3): δ = 34.6, 55.7,
66.5, 116.1, 116.8, 118.2, 119.6, 122.7, 123.9, 126.6, 129.4, 132.1, 144.7, 154.0, 157.4, 160.2,
172.1 ppm; Found: C, 64.81; H, 4.49; N, 4.15 C19H15NO4S; requires: C, 64.58; H, 4.28; N,
3.96%].
3-(4-chlorophenyl)-2-(2-oxo-2H-chromen-4-yl)thiazolidin-4-one (Table 2, Product 2d):
1H-NMR (400 MHz, CDCl3): 3.75 (d, J = 12.4 Hz, 1H), 3.89 (d, J = 12.4 Hz, 1H), 5.93
(s, 1H), 6.17 (s, 1H, CH), 7.39–7.45 (m, 5H), 7.73 (t, J = 8.1 Hz, 1H) 7.85 (d, J = 7.9 Hz,
2H) ppm; 13C NMR (100 MHz, CDCl3): δ = 34.7, 66.8, 116.2, 117.0, 118.3, 123.0, 125.9,

6
M. GHASHANG ET AL.
127.3, 129.4 (2C), 129.5, 131.7, 145.0, 153.9, 160.4, 172.5 ppm; Found: C, 60.56; H, 3.52; N,
4.12 C18H12ClNO3S; requires: C, 60.42; H, 3.38; N, 3.91%].
2-(6-chloro-2-oxo-2H-chromen-4-yl)-3-phenylthiazolidin-4-one (Table 2, Product 2e):
1H-NMR (400 MHz, CDCl3): 3.75 (d, J = 12.4 Hz, 1H), 3.89 (d, J = 12.4 Hz, 1H), 5.93
(s, 1H), 6.17 (s, 1H, CH), 7.39–7.45 (m, 5H), 7.73 (t, J = 8.1 Hz, 1H), 7.85 (d, J = 7.9 Hz,
2H) ppm; 13C NMR (100 MHz, CDCl3): δ = 34.7, 66.8, 116.2, 117.0, 118.3, 123.0, 125.9,
127.3, 129.4 (2C), 129.5, 131.7, 145.0, 153.9, 160.4, 172.5 ppm; Found: C, 60.59; H, 3.56; N,
4.11 C18H12ClNO3S; requires: C, 60.42; H, 3.38; N, 3.91%].
2-(6-chloro-2-oxo-2H-chromen-4-yl)-3-p-tolylthiazolidin-4-one (Table 2, Product 2f ):
1H-NMR (400 MHz, CDCl3): 2.23 (s, 3H, CH3), 3.74 (d, J = 12.4 Hz, 1H), 3.88 (d,
J = 12.4 Hz, 1H), 5.93 (s, 1H), 6.15 (s, 1H, CH), 7.10 (d, J = 7.9 Hz, 2H), 7.35 (d,
J = 8.0 Hz, 1H), 7.40–7.44 (m, 3H), 7.95(s, 1H) ppm; 13C NMR (100 MHz, CDCl3):
δ = 21.5, 35.0, 66.9, 115.1, 116.3, 117.4, 118.1, 128.7, 129.3, 130.2, 130.6, 132.5, 132.7,
144.7, 153.8, 160.7, 172.1 ppm; Found: C, 61.49; H, 3.94; N, 3.95 C19H14ClNO3S; requires:
C, 61.37; H, 3.79; N, 3.77%].
2-(6-chloro-2-oxo-2H-chromen-4-yl)-3-(4-methoxyphenyl)thiazolidin-4-one (Table 2,
Product 2g): 1H-NMR (400 MHz, CDCl3): 3.75–3.77 (m, 4H, CH3), 3.90 (d, J = 12.4 Hz,
1H), 5.93 (s, 1H), 6.16 (s, 1H, CH), 6.67 (d, J = 7.9 Hz, 2H), 7.21 (d, J = 7.9 Hz, 2H),
7.35 (d, J = 8.1 Hz, 1H), 7.43 (d, J = 8.1 Hz, 1H), 7.94 (s, 1H) ppm; 13C NMR (100 MHz,
CDCl3): δ = 34.2, 56.3, 66.7, 116.3, 116.9, 118.2, 119.3, 124.3, 128.7, 129.8, 130.9, 133.3,
144.7, 154.1, 157.4, 160.3, 172.1 ppm; Found: C, 58.97; H, 3.86; N, 3.84 C19H14ClNO4S;
requires: C, 58.84; H, 3.64; N, 3.61%].
2-(6-chloro-2-oxo-2H-chromen-4-yl)-3-(4-chlorophenyl)thiazolidin-4-one (Table 2, Pro-
1
duct 2h): H-NMR (400 MHz, CDCl3): 3.75 (d, J = 12.4 Hz, 1H), 3.92 (d, J = 12.4 Hz,
1H), 5.93 (s, 1H), 6.21 (s, 1H, CH), 7.35 (d, J = 8.2 Hz, 1H), 7.42–7.44 (m, 3H), 7.84 (d,
J = 7.9 Hz, 2H), 7.95 (s, 1H) ppm; 13C NMR (100 MHz, CDCl3): δ = 34.6, 67.0, 116.7,
118.1, 119.9, 125.7, 128.9, 129.2, 129.3, 129.5, 131.0, 132.8, 144.7, 154.1, 160.3, 172.3 ppm;
Found: C, 55.27; H, 2.98; N, 3.76 C18H11Cl2NO3S; requires: C, 55.12; H, 2.83; N, 3.57%].
2-(5-hydroxy-2-oxo-2H-chromen-4-yl)-3-phenylthiazolidin-4-one (Table 2, Product 2i):
1H-NMR (400 MHz, CDCl3): 3.73 (d, J = 12.4 Hz, 1H), 3.89 (d, J = 12.4 Hz, 1H), 5.87
(s, 1H, CH), 5.89 (s, 1H), 6.53 (d, J = 8.0 Hz, 1H), 7.16–7.41 (m, 7H), 10.97 (s, 1H, OH)
ppm; 13C NMR (100 MHz, CDCl3): δ = 34.1, 67.0, 105.1, 114.9, 115.7, 122.3, 122.9, 125.2,
129.5, 130.1, 132.7, 145.2, 156.1, 159.6, 160.7, 171.5 ppm; Found: C, 63.90; H, 4.03; N, 4.37
C18H13NO4S; requires: C, 63.71; H, 3.86; N, 4.13%].
2-(5-hydroxy-2-oxo-2H-chromen-4-yl)-3-p-tolylthiazolidin-4-one (Table 2, Product 2j):
1H-NMR (400 MHz, CDCl3): 2.22 (s, 3H, CH3), 3.74 (d, J = 12.4 Hz, 1H), 3.91 (d,
J = 12.4 Hz, 1H), 5.87 (s, 1H, CH), 5.89 (s, 1H), 6.53 (d, J = 8.0 Hz, 1H), 7.11 (d,
J = 7.9 Hz, 2H), 7.26 (d, J = 8.0 Hz, 1H), 7.40–7.43 (m, 3H), 11.25 (s, 1H, OH) ppm;
13C NMR (100 MHz, CDCl3): δ = 21.4, 33.8, 66.7, 104.9, 114.7, 115.3, 116.7, 122.2, 129.2,
130.1, 132.6, 133.0, 145.2, 155.9, 159.4, 160.1, 171.2 ppm; Found: C, 64.76; H, 4.50; N, 4.11
C19H15NO4S; requires: C, 64.58; H, 4.28; N, 3.96%].
2-(5-hydroxy-2-oxo-2H-chromen-4-yl)-3-(4-methoxyphenyl)thiazolidin-4-one (Table 2,
Product 2k): 1H-NMR (400 MHz, CDCl3): 3.81 (s, 3H, OCH3), 3.75 (d, J = 12.4 Hz, 1H),
3.91 (d, J = 12.4 Hz, 1H), 5.92 (s, 1H, CH), 5.95 (s, 1H), 6.54 (d, J = 8.0 Hz, 1H), 6.69 (d,
J = 7.9 Hz, 2H), 7.18 (d, J = 7.9 Hz, 2H), 7.26 (d, J = 8.0 Hz, 1H), 7.42 (d, J = 8.0 Hz,

JOURNAL OF SULFUR CHEMISTRY
7
1H), 11.05 (s, 1H, OH) ppm; 13C NMR (100 MHz, CDCl3): δ = 34.6, 56.3, 66.7, 105.1,
114.7, 115.6, 115.8, 122.6, 123.9, 124.1, 129.2, 133.1, 144.7, 156.1, 157.3, 159.3, 160.1,
171.4 ppm; Found: C, 61.98; H, 4.36; N, 3.99 C19H15NO5S; requires: C, 61.78; H, 4.09;
N, 3.79%].
3-(4-chlorophenyl)-2-(5-hydroxy-2-oxo-2H-chromen-4-yl)thiazolidin-4-one (Table 2,
Product 2l): 1H-NMR (400 MHz, CDCl3): 3.76 (d, J = 12.4 Hz, 1H), 3.93 (d, J = 12.4 Hz,
1H), 5.93–5.95 (m, 2H), 6.54 (d, J = 8.1 Hz, 1H), 7.26 (d, J = 8.1 Hz, 1H), 7.39–7.43 (m,
3H), 7.84 (d, J = 7.8 Hz, 2H), 11.31 (s, 1H, OH) ppm; 13C NMR (100 MHz, CDCl3):
δ = 35.1, 66.3, 104.4, 114.5, 115.7, 122.5, 125.7, 129.2, 129.3, 129.4, 132.9, 144.7, 156.2,
159.3, 160.1, 171.9 ppm; Found: C, 57.94; H, 3.43; N, 3.91 C18H12ClNO4S; requires: C,
57.83; H, 3.24; N, 3.75%].
2,3-diphenylthiazolidin-4-one (Table 3, Product 3a): 1H-NMR (400 MHz, CDCl3): 3.82
(d, J = 14.1 Hz, 1H), 3.94 (d, J = 14.1 Hz, 1H), 6.02 (s, 1H), 7.16–7.37
(m, 10H).
3-phenyl-2-p-tolylthiazolidin-4-one (Table 3, Product 3b): 1H-NMR (400 MHz, CDCl3):
2.27 (s, 3H, CH3), 3.85 (d, J = 14.2 Hz, 1H), 3.96 (d, J = 14.2 Hz, 1H), 6.07 (s, 1H),
7.08–7.30 (m, 9H).
2-(4-methoxyphenyl)-3-phenylthiazolidin-4-one (Table 3, Product 3c): 1H-NMR
(400 MHz, CDCl3): 3.85 (d, J = 14.1 Hz, 1H), 3.76 (s, 3H, OCH3), 3.96 (d, J = 14.1 Hz,
1H), 6.03 (s, 1H), 6.93 (d, J = 7.6 Hz, 2H), 7.08–7.29 (m, 7H).
2-(4-chlorophenyl)-3-phenylthiazolidin-4-one (Table 3, Product 3d): 1H-NMR
(400 MHz, CDCl3): 3.86 (d, J = 14.2 Hz, 1H), 3.98 (d, J = 14.2 Hz, 1H), 6.06 (s, 1H),
7.11–7.44 (m, 9H).
2-phenyl-3-p-tolylthiazolidin-4-one (Table 3, Product 3e): 1H-NMR (400 MHz, CDCl3):
2.22 (s, 3H, CH3), 3.88 (d, J = 14.4 Hz, 1H), 3.99 (d, J = 14.4 Hz, 1H), 6.03 (s, 1H), 7.10
(d, J = 7.8 Hz, 2H), 7.15–7.36 (m, 7H).
2,3-dip-tolylthiazolidin-4-one (Table 3, Product 3f ): 1H-NMR (400 MHz, CDCl3): 2.21
(s, 3H, CH3), 2.27 (s, 3H, CH3), 3.86 (d, J = 14.3 Hz, 1H), 3.97 (d, J = 14.3 Hz, 1H), 6.02
(s, 1H), 7.03–7.30 (m, 8H).
2-(4-methoxyphenyl)-3-p-tolylthiazolidin-4-one (Table 3, Product 3g): 1H-NMR
(400 MHz, CDCl3): 2.22 (s, 3H, CH3), 3.86 (d, J = 14.1 Hz, 1H), 3.74 (s, 3H, OCH3), 3.98
(d, J = 14.1 Hz, 1H), 6.01 (s, 1H), 6.90 (d, J = 7.5 Hz, 2H),7.08–7.29 (m, 6H).
2-(4-chlorophenyl)-3-p-tolylthiazolidin-4-one (Table 3, Product 3h): 1H-NMR
(400 MHz, CDCl3): 2.22 (s, 3H, CH3), 3.85 (d, J = 14.2 Hz, 1H), 3.97 (d, J = 14.2 Hz, 1H),
6.11 (s, 1H), 7.08 (d, J = 7.5 Hz, 2H), 7.29–7.48 (m, 6H).
2-o-tolyl-3-p-tolylthiazolidin-4-one (Table 3, Product 3i): 1H-NMR (400 MHz, CDCl3):
2.22 (s, 3H, CH3), 2.26 (s, 3H, CH3), 3.85 (d, J = 14.1 Hz, 1H), 3.97 (d, J = 14.1 Hz, 1H),
6.02 (s, 1H), 7.08–7.30 (m, 8H).
2-(2-chlorophenyl)-3-p-tolylthiazolidin-4-one (Table 3, Product 3j): 1H-NMR (400 MHz,
CDCl3): 2.22 (s, 3H, CH3), 3.87 (d, J = 14.1 Hz, 1H), 3.98 (d, J = 14.1 Hz, 1H), 6.12 (s,
1H), 7.08 (d, J = 7.5 Hz, 2H), 7.25–7.44 (m, 6H).
2-(3-nitrophenyl)-3-p-tolylthiazolidin-4-one (Table 3, Product 3k): 1H-NMR (400 MHz,
CDCl3): 2.22 (s, 3H, CH3), 3.88 (d, J = 14.4 Hz, 1H), 4.02 (d, J = 14.4 Hz, 1H), 6.21
(s, 1H), 7.08 (d, J = 7.8 Hz, 2H), 7.39 (d, J = 7.8 Hz, 2H), 7.54 (t, J = 7.6 Hz, 1H), 7.93
(d, J =7.6 Hz, 1H), 8.09 (d, J = 7.6 Hz, 1H), 8.21 (s, 1H).

8
M. GHASHANG ET AL.
Acknowledgments
We are thankful to the Najafabad Branch, Islamic Azad University Research Council for partial
support of this research.
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