Natural eutectic salts catalyzed one-pot synthesis of 5-arylidene-2-imino- 4-thiazolidinones

Article abstract of DOI:10.1007/s11164-012-0707-6

The rapid, very simple and green one-pot synthesis of 5-arylidene-2-imino- 4-thiazolidinones by condensation of the thioureas with chloroacetyl chloride and an aldehyde in natural deep eutectic solvent with good to excellent yields is described.

Full text of DOI:10.1007/s11164-012-0707-6

Res Chem Intermed (2013) 39:1491–1498
DOI 10.1007/s11164-012-0707-6
Natural eutectic salts catalyzed one-pot synthesis
of 5-arylidene-2-imino-4-thiazolidinones
•
Akbar Mobinikhaledi Alireza Khajeh Amiri
Received: 2 April 2012 / Accepted: 26 June 2012 / Published online: 19 July 2012
Ó Springer Science+Business Media B.V. 2012
Abstract The rapid, very simple and green one-pot synthesis of 5-arylidene-2-
imino-4-thiazolidinones by condensation of the thioureas with chloroacetyl chloride
and an aldehyde in natural deep eutectic solvent with good to excellent yields is
described.
Keywords Thiazolidinones ꢀ One-pot synthesis ꢀ Deep eutectic solvent ꢀ
Green chemistry
Introduction
Due to the growing concern for the influence of the organic harmful solvents on the
environment, organic reactions in green media have attracted considerable attention
for organic chemists in recent years. Green chemistry is an innovative way for
designing simple chemical processes and methods in order to eliminate or reduce
the use of hazardous and toxic chemicals at any stage of production in the industry
or laboratory [1].
Ionic liquids are considered as green alternative media for volatile organic
solvents because of their low vapor pressures. They also have several other
attractive properties, including chemical and thermal stability, nonflammability,
high ionic conductivity, and a wide electrochemical potential window. Unfortu-
nately, the high cost and toxicity of some aquatic species are the main disadvantages
of these green solvents, which has limited their applications in laboratory and
industry [2, 3]. Deep eutectic solvents (DESs), eutectic mixtures of an ammonium
salt and a hydrogen-bond donor compound such as urea, acid, amine, and salts,
developed by Abbott and co-workers [4, 5], are alternatives to ionic liquids.
A. Mobinikhaledi (&) ꢀ A. K. Amiri
Department of Chemistry, Faculty of Science, Arak University, 38156-8-8349 Arak, Iran
e-mail: akbar_mobini@yahoo.com
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A. Mobinikhaledi, A. K. Amiri
These eutectic mixtures are attractive alternatives to room temperature ionic liquids,
as DESs can be less expensive, more synthetically available, nontoxic, and
biodegradable [4–7].
Thiazolidin-4-ones derivatives constitute an important class of heterocyclic
compounds due to their applications in organic synthesis, dyes, and in diverse
biological and pharmaceutical activities [8–16]. Several synthetic routes have been
developed for the preparation of substituted 2-imino-thiazolidin-4-ones [11, 17–25].
The most common synthetic pathway is the cyclization of substituted thioureas with
a halo acetic acid derivative to form the corresponding 2-imino-thiazolidin-4-one
derivatives [26–28]. However, most methods use a two- or three-step procedure and
only one example used one-pot multicomponent reactions for the synthesis of
5-arylidene-2-imino-4-thiazolidinones under microwave irradiation [29]. During the
course of our study on the environmentally benign organic synthesis, we have been
particularly interested in one-pot synthesis of some novel 5-arylidene-2-imino-4-
thiazolidinones derivatives under green reaction media in order to develop
environmentally benign reactions [30–32].
Results and discussion
The general synthetic strategy employed for preparation is based on one-pot
reaction of thiourea, chloroacetyl chloride, and aromatic aldehydes in natural deep
eutectic solvent.
First, we embarked upon a series of experiments to establish the optimum
conditions on the model reaction. Our first finding showed that three component
reaction of N,N0-diphenylthiourea [33] 1 (1 mmol) with chloroacetyl chloride 2
(1.2 mmol) and benzaldehyde 3 (1 mmol) in urea/choline chloride (2:1)-based
solvent (0.2 mL) under thermal heating at 80 °C for 30 min was an excellent
reaction condition, and 5-benzylidene-3-phenyl-2(phenylimino)thiazolidin-4-one 4
was obtained in 94 % yield (Scheme 1).
After determining the optimized reaction conditions, we investigated the
generality and scope of the one-pot three-component reaction with a variety of
thiourea 5 and various aldehydes 6 to give 5-arylidene-2-imino-4-thiazolidinones 7
(Scheme 2).
As shown in Table 1, the yield of the products is not affected by the nature of the
thiourea. In the case of thiourea with electron-donating and electron-withdrawing
O
H
H
N
S
ChCl / 2 Urea( 0.2 mL)
30 min, 80oC
N
N
Cl
H
Cl
+
+
N
S
O
O
2
1
3
4
Scheme 1 The model reaction for optimization of reaction conditions
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Natural eutectic salts catalyzed one-pot synthesis
1493
Ar
N
Ar'
O
H
H
S
N
N
ChCl / 2 Urea( 0.2 mL)
30-60 min, 80oC
Cl
Ar'
+
H
Ar
Ar
Cl
+
N
S
O
Ar
6
O
5
7
Scheme 2 Synthetic pathway of thiazolidinone derivatives
Table 1 Diverse derivatives of 5-arylidene-2-imino-4-thiazolidinones 7
Entry
Ar
Ar’
Mp (°C)
Yield (%)
1
Ph
Ph
214–216 (216) [26]
227–229
203–205
254–256
319–321
168–170
196–198
198–200
145–147
236–238
225–227
252–254
189–191
224–226
302–304
197–199
202–203
94
85
70
80
72
83
80
87
80
67
80
75
70
80
73
75
73
2
Ph
4-Cl-Ph
3
Ph
4-OCH3-Ph
2-OH-Ph
4-OH-Ph
4-Cl-Ph
4
Ph
5
Ph
6
4-Cl-Ph
7
4-Cl-Ph
2,6-di-Cl-Ph
4-Cl-Ph
8
4-Et-Ph
9
4-But-Ph
4-But-Ph
2,3-di-CH3-Ph
2,3-di-CH3-Ph
2,3-di-CH3-Ph
2,4,6-tri-CH3-Ph
2,4,6-tri-CH3-Ph
2,4,6-tri-CH3-Ph
2,4,6-tri-CH3-Ph
3-NO2-Ph
Indole-3-yl
4-Cl-Ph
10
11
12
13
14
15
16
17
2-OH-Ph
2,4-di-OH-Ph
Ph
2-OH-Ph
4-CH3-Ph
4-OCH3-Ph
Isolated yield (%)
groups, as well as hindered groups, gave the desired product in good yields. The
scope of the simple reaction was extended to aldehyde substrates, and the results
indicated that commercially available aromatic aldehydes were good substrates and
gave the products in good yields. The structure of all compounds was established by
1
analysis of their H and 13C NMR spectroscopy as well as microanalysis data. The
1
Z configuration of the exocyclic C=C bond was assigned on the basis of H NMR
spectroscopy, according to literature data for analogous 4-thiazolidinones [10, 29,
32].
Experimental
All chemicals including (2-hydroxyethyl)trimethylammonium chloride (known as
choline chloride) were purchased from Merck or Fluka. Melting points were
determined using an electro-thermal digital apparatus and are uncorrected. Purity of
the compound was checked by Thin Layer Chromatography (TLC) using ethyl
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acetate/petroleum ether (1:10 v/v) as an eluent. IR spectra were prepared on a
1
galaxy series FT–IR 5000 spectrophotometer using KBr discs. H NMR spectra
were recorded on Bruker spectrophotometer (300 MHz) in DMSO d6 or CDCl3
using TMS as an internal standard. Microanalyses were performed by the Elemental
Analyzer (Elemental, Vario EL III) at the Arak University. The microanalyses
results agreed favorably with the calculated values.
General procedure for synthesis of 5-arylidene-2-imino-4-thiazolidinones (4)
A mixture of aldehyde (1 mmol), thiourea (1 mmol), and chloroacetyl chloride
(1.2 mmol) in urea–choline chloride (2:1), (0.2 mL) was added to a test tube with a
magnetic stirring bar. The test tube was heated in an oil bath at 80 °C for 30–60 min
(progress of the reaction was followed by TLC) and then was slowly cooled to room
temperature. The resulting precipitate was filtered, and washed with hot water and
ethanol to give pure thiazolidinones. For most of the reactions, appropriate
recrystalization from CHCl3 was used for further purification.
Preparation of deep eutectic solvent
The general route for the synthesis of the ionic liquid was as follow: choline
chloride (100 mmol) was mixed with urea (200 mmol) and heated to ca. 100 °C in
air with stirring until a clear colorless liquid was obtained.
Entry 1: (2Z,5Z)-5-benzylidene-3-phenyl-2-(phenylimino)thiazolidin-4-one 1H N-
MR (300 MHz, CDCl3): d = 7.00–7.94 (m, 15H), 8.13 (s, 1H); 13C NMR (75 MHz,
CDCl3): d = 121.1, 121.2, 124.9, 128.1, 129.0, 129.1, 129.3, 129.4, 129.9, 130.0,
131.6, 133.6, 134.6 (CH=C), 148.1, 151.2 (C=N), 166.4 (C=O); IR (KBr, cm-1):
1,639 (C=N), 1,712 (C=O), Anal. Calcd for C22H16N2OS : C, 74.13; H, 4.52; N,
7.86; S, 9.00. Found: C, 74.41; H, 4.61; N, 7.98; S, 9.21.
Entry 2: (2Z,5Z)-5-(4-chlorobenzylidene)-3-phenyl-2-(phenylimino)thiazolidin-4-
one 1H NMR (300 MHz, CDCl3): d = 6.98–7.60 (m, 14H), 7.79 (s, 1H); 13C
NMR (75 MHz, CDCl3): d = 121.0, 121.9, 125.0, 128.0, 129.0, 129.3, 129.4,
130.1, 131.1, 131.3, 132.1,134.5 (CH=C), 135.9, 147.9, 150.7 (C=N), 166.2 (C=O);
IR (KBr, cm-1): 1,650 (C=N), 1,716 (C=O), Anal. Calcd for C22H15N2OSCl : C,
67.70; H, 3.87; N, 7.17; S, 8.20. Found: C, 67.86; H, 3.97; N, 7.01; S, 8.41.
Entry 3: (2Z,5Z)-5-(4-methoxybenzylidene)-3-phenyl-2-(phenylimino)thiazolidin-4-
one 1H NMR (300 MHz, CDCl3): d = 3.85 (s, 3H), 6.96–7.56 (m, 14H), 7.85 (s,
1H); 13C NMR (75 MHz, CDCl3): d = 55.4, 114.6, 118.3, 121.2, 124.8, 126.4,
128.1, 128.3, 128.9, 129.3, 131.4, 132.0, 134.9, 148.4, 151.3, 161.0, 166.6; IR (KBr,
cm-1): 1,640 (C=N), 1,710 (C=O), Anal. Calcd for C23H18N2O2S : C, 71.48; H,
4.69; N, 7.25; S, 8.30. Found: C, 71.27; H, 4.60; N, 7.30; S, 8.37.
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Natural eutectic salts catalyzed one-pot synthesis
1495
Entry 4: (2Z,5Z)-5-(2-hydroxybenzylidene)-3-phenyl-2-(phenylimino)thiazolidin-4-
one 1H NMR (300 MHz, DMSO-d6): d = 6.72–7.41 (m, 14H), 8.11 (s, 1H), 9.45
(1H, brs, OH); IR (KBr, cm-1): 1,691 (C=N), 1,714 (C=O), 3,260 (OH), Anal.
Calcd for C22H16N2O2S : C, 70.95; H, 4.33; N, 7.52; S, 8.61. Found: C, 70.72; H,
4.55; N, 7.61; S, 8.49.
Entry 5: (2Z,5Z)-5-(4-hydroxybenzylidene)-3-phenyl-2-(phenylimino)thiazolidin-4-
one 1H NMR (300 MHz, DMSO-d6): d = 6.88–7.58 (m, 14H), 7.72 (s, 1H), 10.26
(s, 1H, OH); 13C NMR (75 MHz, DMSO-d6): d = 117.1, 121.2, 124.7, 125.1,
129.0, 129.5, 129.9, 131.4, 132.6, 135.5, 148.5, 151.1, 160.0, 166.3 (C=O), Anal.
Calcd for C22H16N2O2S : C, 70.95; H, 4.33; N, 7.52; S, 8.61. Found: C, 80.10; H,
4.21; N, 7.47; S, 8.75.
Entry 6: (2Z,5Z)-5-(4-chlorobenzylidene)-3-(4-chlorophenyl)-2-(4-chlorophenylimi-
no)thiazolidin-4-one 1H NMR (300 MHz, CDCl3): d = 6.91–7.55 (m, 12H), 7.80
(s, 1H); 13C NMR (75 MHz, CDCl3): d = 121.1, 122.4, 129.3, 129.4, 129.5, 129.6,
130.5, 130.8, 131.2, 131.8, 132.7, 135.0 (CH=C), 136.2, 146.3, 151.0 (C=N), 165.9
(C=O); IR (KBr, cm-1): 1,652 (C=N), 1,715 (C=O), Anal. Calcd for
C22H13N2OSCl3 : C, 57.47; H, 2.85; N, 6.09; S, 6.97. Found: C, 57.19; H, 2.99;
N, 6.15; S, 6.84.
Entry 7: (2Z,5Z)-5-(2,6-di-chlorobenzylidene)-3-(4-chlorophenyl)-2-(4-chlorophe-
nylimino) thiazolidin-4-one 1H NMR (300 MHz, CDCl3): d = 6.85–7.56 (m,
11H), 7.82 (s, 1H); IR (KBr, cm-1): 1,633 (C=N), 1,712 (C=O), Anal. Calcd for
C22H12N2OSCl4 : C, 53.47; H, 2.45; N, 5.67; S, 6.49. Found: C, 53.69; H, 2.30; N,
5.51; S, 6.51.
Entry 8: (2Z,5Z)-5-(4-chlorobenzylidene)-3-(4-ethylphenyl)-2-(4-ethylphenylimino)
thiazolidin-4-one 1H NMR (300 MHz, CDCl3): d = 1.29 (t, 6H, J = 7.2 Hz),
2.73 (q, 4H, J = 9.5 Hz), 6.92–7.48 (m, 12H), 7.92 (s, 1H); 13C NMR (75 MHz,
CDCl3): d = 15.3, 28.3, 120.9, 121.7, 122.2, 127.0, 127.7, 128.6, 128.8, 129.0,
129.3,129.6, 129.7, 131.1, 131.4, 131.7, 132.2, 132.8, 135.7, 136.7, 140.9, 145.0,
145.6, 150.3 (C=N), 166.4 (C=O); IR (KBr, cm-1): 1,645 (C=N), 1,705 (C=O),
Anal. Calcd for C26H23N2OSCl : C, 69.86; H, 5.19; N, 6.27; S, 7.17. Found: C, 69.6;
H, 5.34; N, 6.46; S, 6.91.
Entry 9: (2Z,5Z)-5-(3-nitrobenzylidene)-3-(4-butylphenyl)-2-(4-butylphenylimino)
thiazolidin-4-one 1H NMR (300 MHz, CDCl3): d = 0.97 (t, 6H, J = 6.9 Hz),
1.35–1.45 (m, 4H), 1.58–1.68 (m, 4H), 2.61–2.71 (m, 4H), 6.89–8.23 (m, 12H), 8.33
(s, 1H); 13C NMR (75 MHz, CDCl3): d = 14.0, 22.4, 22.5, 33.3, 33.6, 35.1, 35.4,
120.7, 123.8, 124.6, 125.2, 127.6, 127.9, 129.3, 129.4, 130.1, 131.9, 134.7, 135.5,
139.9, 143.9, 145.4, 148.6, 149.3, 166.0 (C=O); IR (KBr, cm-1): 1,643 (C=N),
1,718 (C=O), Anal. Calcd for C30H31N3O3S: C, 70.15; H, 6.08; N, 8.18; S, 6.24.
Found: C, 69.90; H, 6.25; N, 8.01; S, 6.11.
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Entry 10: (2Z,5Z)-5-(1H-indole-3-yl)methylene)-3-(4-butylphenyl)-2-(4-butylphe-
nylimino) thiazolidin-4-one 1H NMR (300 MHz, CDCl3): d = 0.93 (t, 6H,
J = 7.7 Hz), 1.28–1.45 (m, 4H), 1.57–1.68 (m, 4H), 2.61–2.66 (m, 4H),
6.94–7.85 (m, 13H), 8.18 (s, 1H), 8.91 (1H, brs, NH); 13C NMR (75 MHz, CDCl3):
d = 13.9, 14.0, 22.3, 22.4, 33.2, 33.6, 35.1, 35.4, 111.6, 112.4, 115.8, 118.7, 121.0,
121.4, 123.2, 123.6, 126.5, 127.0, 127.7, 129.1, 129.2, 132.5, 135.7, 139.3, 143.6,
146.2, 151.3, 166.8; IR (KBr, cm-1): 1,637 (C=N), 1,689 (C=O), 3,263 (NH), Anal.
Calcd for C32H33N3OS: C, 75.70; H, 6.55; N, 8.28; S, 6.32. Found: C, 75.94; H,
6.39; N, 8.34; S, 6.49.
Entry 11: (2Z,5Z)-5-(4-chlorobenzylidene)-3-(2,3-dimethylphenyl)-2-(2,3-dimethyl-
phenylimino)thiazolidin-4-one 1H NMR (300 MHz, CDCl3): d = 2.06 (s, 3H),
2.23 (s, 3H), 2.31 (s, 3H), 2.40 (s, 3H), 6.74–7.41 (m, 10H), 7.80 (s, 1H); 13C NMR
(75 MHz, CDCl3): d = 13.9, 14.4, 20.3, 20.5, 117.9, 122.1, 125.9, 126.0, 126.7,
126.8, 128.3, 129.3, 130.0, 131.3, 131.4, 132.1, 133.8, 134.7 (CH=C), 135.8, 137.9,
138.6, 146.5, 150.2 (C=N), 166.2 (C=O); IR (KBr, cm-1): 1,649 (C=N), 1,720
(C=O), Anal. Calcd for C26H23N2OSCl: C, 69.86; H, 5.19; N, 6.27; S, 7.17. Found:
C, 70.05; H, 5.01; N, 6.22; S, 7.34.
Entry 12: (2Z,5Z)-5-(2-hydroxybenzylidene)-3-(2,3-dimethylphenyl)-2-(2,3-dimeth-
ylphenylimino)thiazolidin-4-one 1H NMR (300 MHz, DMSO-d6): d = 1.96 (s,
3H), 2.11 (s, 3H), 2.22 (s, 3H), 2.33 (s, 3H), 6.67–7.28 (m, 10H), 8.03 (s, 1H), 10.49
(1H, brs, OH); 13C NMR (75 MHz, DMSO-d6): d = 13.9, 14.4, 20.3, 20.5, 116.4,
117.9, 120.1, 120.3, 120.7, 126.3, 126.4, 126.6, 126.7, 127.0, 127.8, 128.8, 131.0,
132.3, 134.8 (CH=C),135.0, 137.9, 138.3, 147.0, 150.2 (C=N), 157.3, 166.1 (C=O);
IR (KBr, cm-1): 1,646 (C=N), 1,715 (C=O), 3,221 (brs, OH), Anal. Calcd for
C26H24N2O2S: C, 72.87; H, 5.64; N, 6.54; S, 7.48. Found: C, 72.70; H, 5.50; N,
6.69; S, 7.42.
Entry 13: (2Z,5Z)-5-(2,4-dihydroxybenzylidene)-3-(2,3-dimethylphenyl)-2-(2,3-dim-
ethylphenylimino)thiazolidin-4-one 1H NMR (300 MHz, DMSO): d = 1.91 (s,
3H), 2.08 (s, 3H), 2.20 (s, 3H), 2.23 (s, 3H), 6.41–7.29 (m, 9H), 7.98 (s, 1H), 10.20
(brs, OH), 10.43(brs, OH); 13C NMR (75 MHz, CDCl3): d = 13.8, 14.3, 19.0, 20.3,
117.8, 126.1, 126.2, 126.6, 126.9, 127.5, 130.7,135.0, 135.1, 137.7, 138.2, 147.1,
155.1, 171.9 (C=O); IR (KBr, cm-1): 1,691 (C=N), 1,712 (C=O), 3,381 (OH), Anal.
Calcd for C26H24N2O3S: C, 70.25; H, 5.44; N, 6.30; S, 7.21. Found: C; 70.48; H,
5.59; N, 6.39; S, 7.02.
Entry 14: (2Z,5Z)-5-benzylidene-3-(2,4,6-trimethylphenyl)-2-(2,4,6-trimethylphe-
nylimino) thiazolidin-4-one 1H NMR (300 MHz, CDCl3): d = 1.97 (s, 6H), 2.12
(s, 6H), 2.30 (s, 3H), 2.45 (s, 3H), 6.82–7.63 (m, 9H), 7.90 (s, 1H); 13C NMR
(75 MHz, CDCl3): d = 17.7, 18.3, 20.9, 21.3, 121.3, 128.1, 128.4, 129.0, 129.1,
129.7, 129.9, 130.1, 131.5, 133.6, 133.9, 135.8 (CH=C), 139.6, 143.3, 151.0 (C=N),
166.1 (C=O); IR (KBr, cm-1): 1,645 (C=N), 1,720 (C=O), Anal. Calcd for
123

Natural eutectic salts catalyzed one-pot synthesis
1497
C28H28N2OS: C, 76.33; H, 6.41; N, 6.36; S, 7.28. Found: C, 76.05; H, 6.52; N, 6.27;
S, 7.35.
Entry 15: (2Z,5Z)-5-(2-hydroxybenzylidene)-3-(2,4,6-trimethylphenyl)-2-(2,4,6-tri-
methylphenylimino)thiazolidin-4-one 1H NMR (300 MHz, DMSO-d6): d = 2.00
(s, 6H), 2.17 (s, 6H), 2.31 (s, 3H), 2.50 (s, 3H), 6.83–7.29 (m, 8H), 10.51 (s, 1H,
OH); 13C NMR (75 MHz, DMSO-d6): d = 17.6, 18.1, 20.8, 21.0, 116.5, 119.7,
120.1, 133.5, 136.0, 139.1, 143.5, 150.2, 157.4 (C=N), 165.7 (C=O); IR (KBr,
cm-1): 1,639 (C=N), 1,718 (C=O), 3,186 (brs, OH); MS(m/z, %) : 456(M?),
278,160, Anal. Calcd for C28H28N2O2S: C, 73.65; H, 6.18; N, 6.14; S, 7.02. Found:
C, 73.39; H, 6.28; N, 6.38; S, 6.88.
Entry 16: (2Z,5Z)-5-(4-methylbenzylidene)-3-(2,4,6-trimethylphenyl)-2-(2,4,6-trim-
ethylphenylimino)thiazolidin-4-one 1H NMR (300 MHz, CDCl3): d = 2.05 (s,
6H), 2.23 (s, 12H), 2.38 (s, 3H), 6.76–7.40 (m, 8H), 7.84 (s, 1H); 13C NMR
(75 MHz, CDCl3); d = 17.7, 18.3, 20.9, 21.3, 21.5, 119.9, 128.3, 129.0, 129.7,
129.8, 130.2, 130.7, 131.8, 134.0, 135.8, 139.6, 140.6, 143.0, 166.1 (C=O); IR (KBr,
cm-1) 1,641 (C=N), 1,712 (C=O), Anal. Calcd for C29H30N2OS: C, 76.61; H, 6.65;
N, 6.16; S, 7.05. Found: C, 76.87; H, 6.74; N, 6.01; S, 7.18.
Entry 17: (2Z,5Z)-5-(4-methoxybenzylidene)-3-(2,4,6-trimethylphenyl)-2-(2,4,6-
trimethylphenylimino) thiazolidin-4-one 1H NMR (300 MHz, CDCl3): d = 2.16
(s, 6H), 2.30 (s, 9H), 2.35 (s, 3H), 3.85 (s, 3H, OCH3), 6.88–7.45 (m, 8H), 7.82 (s,
1H); 13C NMR (75 MHz, CDCl3): d = 17.8, 18.3, 21.0, 55.4, 114.6, 118.5, 126.3,
128.1, 129.0, 129.7, 130.6, 131.2, 132.1, 133.7, 135.9 (CH=C), 139.5, 143.8, 150.8,
160.9, 166.3 (C=O); IR (KBr, cm-1) 1,639 (C=N), 1,705 (C=O), MS (m/z, %): 470
(M?), 278 (100), 202, Anal. Calcd for C29H30N2O2S: C, 74.01; H, 6.43; N, 5.95; S,
6.81. Found: C, 73.75; H, 6.51; N, 5.70; S, 6.98.
Conclusion
In summary, we have developed a mild and rapid procedure for green synthesis of
various 4-thiazolidinones in good to excellent yields in natural deep eutectic solvent
as a catalyst and reaction media. The reaction was carried out via a one-pot reaction
of reactants in a green solvent followed by simple purification.
Acknowledgment Financial support of this study provided by Arak University is gratefully
appreciated.
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2. N.V. Plechkova, K.R. Seddon, Chem. Soc. Rev. 37, 123 (2008)
3. N.V. Plechkova, K.R. Seddon, P. Tundo, A. Perosa, F. Zecchini, Methods Reag. Green Chem. 105,
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