An efficient and convenient protocol for the synthesis of thiazolidin-4-ones

Article abstract of DOI:10.1080/10426507.2011.608099

Without a catalyst and under solvent-free conditions, 2,3-disubstituted-1, 3- thiazolidin-4-one 5a-j derivatives were synthesized efficiently via the three-component reaction of aryl hydrazide, aromatic aldehyde, and mercaptoacetic acid. All the newly synthesized compounds were confirmed by IR, ¹H NMR, and ¹³C NMR spectroscopy and elemental analysis. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/10426507.2011.608099

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Phosphorus, Sulfur, and Silicon and the
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An Efficient and Convenient Protocol for
the Synthesis of Thiazolidin-4-Ones
S. Ebrahimi a , A. Mobinikhaldei b & H. Eibagi b
a Department of Chemistry, Malayer Branch , Islamic Azad
University , Malayer, Iran
b Department of Chemistry , Arak University , Arak, Iran
Published online: 31 Oct 2011.
To cite this article: S. Ebrahimi , A. Mobinikhaldei & H. Eibagi (2011) An Efficient and Convenient
Protocol for the Synthesis of Thiazolidin-4-Ones, Phosphorus, Sulfur, and Silicon and the Related
Elements, 186:12, 2279-2285, DOI: 10.1080/10426507.2011.608099
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Phosphorus, Sulfur, and Silicon, 186:2279–2285, 2011
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2011.608099
AN EFFICIENT AND CONVENIENT PROTOCOL
FOR THE SYNTHESIS OF THIAZOLIDIN-4-ONES
S. Ebrahimi,1 A. Mobinikhaldei,2 and H. Eibagi2
1Department of Chemistry, Malayer Branch, Islamic Azad University,
Malayer, Iran
2Department of Chemistry, Arak University, Arak, Iran
GRAPHICAL ABSTRACT
O
Ar
N NH2
Ar
H
Route A
O
AcOH
O
1a-b
HN
N
CHO
HS
OH
R
4
3a-j
2a-j
R
R
O
OH
CHO
S
O
Ar
N NH2
Route B
H
N
H
N
O
R
O
5a-j
HS
4
Ar
1a-b
Ar= 3-pyridyl, 4-pyridyl
R= H, 4-Me, 3-Br, 2-Cl, 4-Cl, 2-NO2, 3-NO2, 4-NO2
2a-j
Abstract Without
a catalyst and under solvent-free conditions, 2,3-disubstituted-1,3-
thiazolidin-4-one 5a–j derivatives were synthesized efficiently via the three-component
reaction of aryl hydrazide, aromatic aldehyde, and mercaptoacetic acid. All the newly
synthesized compounds were confirmed by IR, 1H NMR, and 13C NMR spectroscopy and
elemental analysis.
Keywords Thiazolidin-4-one; multicomponent; isonicotinohydrazide; nicotinohydrazide;
mercaptoacetic acid
INTRODUCTION
Synthetic modifications in which highly functionalized organic molecules can be
produced from easily available substrates via atom-efficient reactions have special impor-
tance for the organic chemists, for example, in expeditious domino and multicomponent
Received 9 June 2011; accepted 21 July 2010.
We are thankful to Malayer Branch, Islamic Azad University, for their financial support.
Address correspondence to S. Ebrahimi, Department of Chemistry, Malayer Branch, Islamic Azad Univer-
sity, Malayer, Iran. E-mail: seyonesi@iau-malayer.ac.ir
2279

2280
S. EBRAHIMI ET AL.
reactions (MCRs).1 In these reactions, three, four, or five easily accessible components
react to form a single product, which incorporates essentially all the carbon atoms of the
starting materials.2
The Thiazolidin-4-one ring system is a core structure in various synthetic phar-
maceutical compounds, displaying a broad spectrum of biological activities.3–8 Several
synthetic methods have been developed for the synthesis of thiazolidin-4-ones. The main
synthetic routes to thiazolidin-4-ones involve cyclocondensation of azomethines (Schiff’s
base) with mercaptoacetic acid.9 There are also reports of using chemical agents such as
N,N-dicyclohexyl carbodiimide (DCC)10 as desiccant to assist the formation of thiazolidi-
none derivatives. The use of ionic liquid,11 Hunig’s base,12 and KSF Montmorillonite,13 has
also been reported to expedite the cyclocondensation of the azomethines and thioglycolic
acid. However these methodologies suffer from one or more disadvantages such as costly
dehydrating agents and require prolonged heating and tedious work-up. Therefore it was
thought worthwhile to develop a new method for the cyclocondensation. In continuation
of our effort to develop the synthesis of new heterocyclic using the reaction of azome-
thines with nucleophile,14 we report, herein, multicomponent procedure for the synthesis
of thiazolidinone compounds without the use of a catalyst.
RESULTS AND DISCUSSION
In the present study, we report our results on a new type of the MCR where three
organic components react to form novel compounds. Two strategies were attempted for
the synthesis of thiazolidin-4-ones 5a–j. First, the synthesis of thiazolidin-4-ones was
investigated through a two-step pathway (see Scheme 1, Route A). Initially, the N-
benzylideneisonicotinohydrazide intermediates 3a–j were obtained by refluxing the aryl
hydrazide 1a,b and aromatic aldehyde 2a–j in acetic acid with excellent yields (85%–90%).
O
Ar
N NH2
Ar
H
Route A
O
AcOH
O
1a-b
HN
N
CHO
HS
OH
R
4
3a-j
2a-j
R
R
O
OH
CHO
S
O
Ar
N NH2
Route B
H
N
H
N
O
R
O
5a-j
HS
4
Ar
1a-b
2a-j
Ar= 3-pyridyl, 4-pyridyl
R= H, 4-Me, 3-Br, 2-Cl, 4-Cl, 2-NO2, 3-NO2, 4-NO2
Scheme 1

SYNTHESIS OF THIAZOLIDIN-4-ONES
2281
Table 1 Thiazolidin-4-one 5a–j
Products
R
Ar
Route A yield (%)
Route B yield (%)
5a
5b
5c
5d
5e
5f
5g
5h
5i
H
4-CH3
3-Br
2-Cl
4-Cl
2-NO2
3-NO2
4-NO2
3- NO2
4-NO2
4-pyridyl
4-pyridyl
4-pyridyl
4-pyridyl
4-pyridyl
4-pyridyl
4-pyridyl
4-pyridyl
3-pyridyl
3-pyridyl
80
70
64
90
85
65
90
85
80
85
70
65
60
90
70
65
85
85
69
72
5j
Subsequently, the thiazolidin-4-ones 5a–j were synthesized from cyclocondensation
reactions of the acyl hydrazones intermediates 3a–j by using excess of mercaptoacetic acid
4, without any solvent at 60◦C (see Scheme 1, Route A). The results are summarized in
Table 1.
We also carried out the synthesis of 2,3-disubstituted-1,3-thiazolidin-4-one 5a–j that
involves the one-pot, three-component condensation reactions of aryl hydrazide, different
aromatic aldehydes, and large excess of thioglycolic acid under solvent-free condition (see
Scheme 1, Route B). The initial reaction using isonicotinohydrazide 1a and aldehyde 2a
at a ratio of 1:1.2, and excess of thioglycolic acid 4, was stirred under 60◦C. When the
reaction was terminated [monitored by thin layer chromatography (TLC)], the expected
product 5a was afforded in a yield of 45%. The yield of 5a increased remarkably with
increasing temperature until 80◦C.
Encouraged by the result obtained above, we extended this process to various alde-
hydes to gain more insight into this reaction (see Scheme 1, Route B). The typical results
are summarized in Table 1. Aromatic aldehydes with substitutes carrying either electron-
donating or electron-withdrawing groups reacted successfully and gave the products in
good yields.
1
The H NMR spectra of all the synthesized compounds reveal a singlet at δ =
5.90–6.30 ppm attributed to the resonance of the methine proton (N CH S). The ap-
pearance of the IR absorptions and 13C-NMR signals, due to the carbonyl group of the
synthesized compounds 5a–j, clearly confirmed the formation of thiazolidin-4-ones.
CONCLUSION
In summary, we reported a novel and efficient method for the synthesis of thiazolidin-
4-ones. The notable advantages of our work are as follows: (1) the reaction is performed
under mild condition and more important is under solvent-free condition, (2) no catalyst is
required for this reaction, (3) good yields of cyclization products without any byproduct,
and (4) simple purification method.
EXPERIMENTAL
Purity of the compounds was checked by TLC using ethyl acetate/n-hexane (1:1 v/v)
1
as an eluent. All products were characterized using IR, H NMR, and 13C NMR spectra.

2282
S. EBRAHIMI ET AL.
All yields refer to isolated products. IR spectra were prepared on a Galaxy series FTIR
5000 spectrophotometer (Perkin Elmer) using KBr discs. NMR spectra were recorded on
Bruker spectrophotometer (300 MHz) in dimethyl sulfoxide-d6 (DMSO-d6) using TMS as
an internal standard. C, H, N, and S analyses were performed on a Vario EL III elemental
analyzer.
General Procedure for the Synthesis of Thiazolidine-4-one 5a–j
Route A. A mixture of acylhydrazone 3a–j (0.1 mol), mercaptoacetic acid
(0.5 mL), was heated at 60◦C under solvent-free conditions for 3 h. The progress of the
reaction was monitored by TLC using n-hexane–ethyl acetate (1:1). After the completion
of the reaction, the mixture was extracted with ethyl acetate and the organic layer was
washed with 5% sodium bicarbonate solution and water. The organic layer was separated
and dried over anhydrous sodium sulfate. From the organic extract, the solvent was
removed under reduced pressure. The residue obtained was triturated with n-hexane (2
mL) and filtered to isolate the solid product, which was then washed with n-hexane (2
mL), and dried to give thiazolidin-4-one 5a–j.
Route B. A mixture of acylhydrazides 1a,b (1 mmol), and appropriate aromatic
aldehyde (1.2 mmol), mercaptoacetic acid (0.5 mL), was stirred at 80 ◦C in an oil bath for
7 h. Then, the reaction mixture was extracted with ethyl acetate and the organic layer was
washed with 5% NaHCO3 solution/water and dried over anhydrous Na2SO4. The crude
solid obtained on evaporation of the solvent under reduced pressure was recrystallized from
ethylacetat/n-xexane to furnish a crystalline solid 5a–j.
N-(4-Oxo-2-phenylthiazolidin-3-yl)isonicotinamide (5a, Table 1)
IR (KBr): υ = 3108 (NH), 3035 (aromatic CH stretch.), 2995 (aliphatic CH stretch.),
1716 (C O), 1682 (C O), 1616 (C N), 1524 (C C) cm−1, 1H NMR (DMSO-d6) δ (ppm):
3.80 (d, 1H, CH2, J = 16.1 Hz), 3.91(d, 1H, CH2, J = 16.2 Hz), 5.91 (s, 1H, S CH N),
7.36–7.47 (m, 5H, Harom.), 7.60 (d, 2H, Harom., J = 5.3 Hz), 8.69 (d, 2H, Harom., J = 5.5
Hz), 11.10 (s, 1H, D2O exchange, NH), 13C NMR (DMSO-d6) δ (ppm): 29.8 (CH2), 62.0
(CH), 121.7, 128.2, 129.1, 129.6, 138.4, 138.9, 150.9, 164.3 (C O), 169.6 (C O), Anal.
Calcd. for: C15H13N3O2S: C, 60.18; H, 4.38; N, 14.04; S, 10.71. Found: C, 60.02; H, 4.31;
N, 13.96; S, 10.64.
N-(4-Oxo-2-p-tolylthiazolidin-3-yl)isonicotinamide (5b, Table 1)
IR (KBr): υ = 3103 (NH), 3020 (aromatic CH stretch.), 2881 (aliphatic CH stretch.),
1721 (C O), 1680 (C O), 1602 (C N), 1514 (C C) cm−1, 1H NMR (DMSO-d6) δ (ppm):
2.29 (s, 3H, CH3), 3.83 (d, 1H, CH2, J = 15.9 Hz), 3.95 (d, 1H, CH2, J = 16.1 Hz), 5.90
(s, 1H, S-CH-N), 7.19 (d, 2H, Harom., J = 7.6 Hz), 7.38 (d, 2H, Harom., J = 7.6 Hz), 7.63 (d,
2H, Harom., J = 4.5 Hz), 8.72 (d, 2H, Harom., J = 4.6 Hz), 11.03 (s, 1H, D2O exchange, NH),
13C NMR (DMSO-d6) δ (ppm): 21.3 (CH3), 29.9 (CH2), 62.0 (CH), 121.77, 128.3, 129.6,
135.3, 138.9, 139.1, 150.9, 164.3 (C O), 169.6 (C O), Anal. Calcd. for: C16H15N3O2S:
C, 61.32; H, 4.82; N, 13.41; S, 10.23. Found: C, 61.22; H, 4.76; N, 13.29; S, 10.09.
N-(2-(3-Bromophenyl)-4-oxothiazolidin-3-yl)isonicotinamide
(5c, Table 1)
IR (KBr): υ = 3110 (NH), 3020 (aromatic CH stretch.), 2924 (aliphatic CH stretch.),
1
1718 (C O), 1685 (C O), 1523 (C C) cm−1, H NMR (DMSO-d6) δ (ppm): 3.83 (d,
1H, CH2, J = 15.8 Hz), 3.98 (d, 1H, CH2, J = 15.6 Hz), 5.94 (s, 1H, S-CH-N), 7.35–7.64

SYNTHESIS OF THIAZOLIDIN-4-ONES
2283
(m, 5H, Harom.), 7.73 (s, 1H, Harom.), 8.74 (d, 2H, Harom., J = 5.5 Hz), 11.10 (s, 1H, D2O
exchange, NH), 13C NMR (DMSO-d6) δ (ppm): 29.6 (CH2), 61.2 (CH), 121.7, 122.3, 127.4,
130.7, 131.2, 132.4, 138.9, 141.6, 151.0, 164.4 (C O), 169.5 (C O), Anal. Calcd. for:
C15H12ClN3O2S: C, 47.63; H, 3.20; N, 11.11; S, 8.48. Found: C, 47.50; H, 3.16; N, 10.98;
S, 8.30.
N-(2-(2-Chlorophenyl)-4-oxothiazolidin-3-yl)isonicotinamide
(5d, Table 1)
IR (KBr): υ = IR (KBr): υ (cm−1): 3107 (NH), 3040 (aromatic CH stretch.), 2879
1
(aliphatic CH stretch.), 1722 (C O), 1682 (C O), 1602 (C N), 1529 (C C) cm−1, H
NMR (DMSO-d6) δ (ppm): 3.84 (d, 1H, CH2, J = 15.9 Hz), 3.99 (d, 1H, CH2, J = 15.8
Hz), 6.28 (s, 1H, S-CH-N), 7.40–7.47 (m, 3H, Harom.), 7.59–7.72 (m, 3H, Harom.), 8.73 (d,
2H, Harom., J = 5.6 Hz), 11.16 (s, 1H, D2O exchange, NH), 13C NMR (DMSO-d6) δ (ppm):
29.3 (CH2), 58.7 (CH), 121.8, 128.4, 129.0, 130.1, 131.0, 132.7, 136.2, 138.9, 151.0, 164.6
(C O), 169.8 (C O). Anal. Calcd. for: C15H12ClN3O2S: C, 53.97; H, 3.62; N, 12.59; S,
9.61. Found: C, 53.69; H, 3.52; N, 12.41; S, 9.50.
N-(2-(4-Chlorophenyl)-4-oxothiazolidin-3-yl)isonicotinamide
(5e, Table 1)
IR (KBr): υ = 3120 (NH), 3010 (aromatic CH stretch.), 2992 (aliphatic CH stretch.),
1720 (C O), 1680 (C O), 1610 (C N) cm−1, 1H NMR (DMSO-d6) δ (ppm): 3.85 (d, 1H,
CH2, J = 16.2 Hz), 3.98 (d, 1H, CH2, J = 16.0 Hz), 5.94 (s, 1H, S-CH-N), 7.45–7.52 (m,
4H, Harom.), 7.63 (d, 2H, Harom., J = 5.6 Hz), 8.72 (d, 2H, Harom., J = 5.5 Hz), 10.96 (s, 1H,
D2O exchange, NH), 13C NMR (DMSO-d6) δ (ppm): 29.7 (CH2), 61.3 (CH), 121.8, 129.1,
130.2, 134.1, 137.7, 138.9, 151.0, 164.3 (C O), C15H12ClN3O2S: C, 53.97; H, 3.62; N,
12.59; S, 9.61. Found: C, 53.72; H, 3.54; N, 12.40; S, 9.54.
N-(2-(4-Nitrophenyl)-4-oxothiazolidin-3-yl)isonicotinamide (5f, Table 1)
IR (KBr): υ = 3120 (NH), 3054 (aromatic CH stretch.), 2941 (aliphatic CH stretch.),
1
1720 (C O), 1688 (C O), 1520 (C C) cm−1, H NMR (DMSO-d6) δ (ppm): 3.78 (d,
1H, CH2, J = 15.5 Hz), 3.96 (d, 1H, CH2, J = 15.4 Hz), 6.30 (s, 1H, S-CH-N), 7.42–7.66
(m, 3H, Harom.), 7.88 (br, 2H, Harom.), 8.07 (s, 1H, Harom.), 8.72 (d, 2H, Harom., J = 5.4 Hz),
11.20 (s, 1H, D2O exchange, NH), 13C NMR (DMSO-d6) δ (ppm): 29.6 (CH2), 57.7 (CH),
121.9, 125.6, 127.9, 128.2, 130.2, 131.6, 135.3, 147.6, 150.8, 164.5 (C O), 170.0 (C O),
Anal. Calcd. for: C15H12N4O4S: C, 52.32; H, 3.51; N, 16.27; S, 9.31. Found: C, 52.21; H,
3.45; N, 16.07; S, 9.14.
N-(2-(3-Nitrophenyl)-4-oxothiazolidin-3-yl)isonicotinamide (5g, Table 1)
IR (KBr): υ = 3115 (NH), 3034 (aromatic CH stretch.), 2931 (aliphatic CH stretch.),
1715 (C O), 1685 (C O), 1521 (C C) cm−1, 1H NMR (DMSO-d6) δ (ppm): 3.83 (d, 1H,
CH2, J = 15.5 Hz), 3.99 (d, 1H, CH2, J = 15.7 Hz), 6.14 (s, 1H, S-CH-N), 7.68 (d, 2H,
Harom., J = 7.5 Hz), 7.92–8.00 (m, 1H, Harom.), 8.22 (br, 1H, Harom.), 8.32 (s, 1H, Harom.),
8.41 (s, 1H, Harom.), 8.70 (d, 2H, Harom., J = 5.6 Hz), 11.18 (br, 1H, D2O exchange, NH),
13C NMR (DMSO-d6) δ (ppm): 30.4 (CH2), 61.1 (CH), 121.7, 123.1, 124.4 130.7, 135.0,
138.8, 141.3, 148.3, 150.9, 164.4 (C O), 169.5 (C O), Anal. Calcd. for: C15H12N4O4S:
C, 52.32; H, 3.51; N, 16.27; S, 9.31. Found: C, 52.18; H, 3.47; N, 16.08; S, 9.21.

2284
S. EBRAHIMI ET AL.
N-(2-(4-Nitrophenyl)-4-oxothiazolidin-3-yl)isonicotinamide (5h, Table 1)
IR (KBr): υ = 3115 (NH), 3078 (aromatic CH stretch.), 2982 (aliphatic CH stretch.),
1722 (C O), 1676 (C O), 1601 (C N), 1521, 1346 (NO2) cm−1, 1H NMR (DMSO-d6)
δ (ppm): 3.87 (d, 1H, CH2, J = 16.0 Hz), 4.05 (d, 1H, CH2, J = 16.1 Hz), 6.09 (s, 1H,
S-CH-N), 7.64 (d, 2H, Harom., J = 5.6 Hz), 7.81 (d, 2H, Harom., J = 8.6 Hz), 8.25 (d, 2H,
Harom., J = 8.5 Hz), 8.73 (d, 2H, Harom., J = 5.6 Hz), 11.16 (s, 1H, D2O exchange, NH),
13C NMR (DMSO-d6) δ (ppm): 29.6 (CH2), 60.9 (CH), 121.8, 124.3, 129.5, 138.7, 146.6,
148.2, 151.0, 164.4 (C O), 169.5 (C O), Anal. Calcd. for: C15H12N4O4S: C, 52.32; H,
3.51; N, 16.27; S, 9.31. Found: C, 52.08; H, 3.36; N, 16.03; S, 9.07.
N-(2-(3-Nitrophenyl)-4-oxothiazolidin-3-yl)nicotinamide (5i, Table 1)
IR (KBr): υ = 3115 (NH), 3064 (aromatic CH stretch.), 2944 (aliphatic CH stretch.),
1
1718 (C O), 1680 (C O), 1551 (C C) cm−1, H NMR (DMSO-d6) δ (ppm): 3.85 (d,
1H, CH2, J = 16.1 Hz), 4.10 (d, 1H, CH2, J = 16.00 Hz), 6.13 (s, 1H, S-CH-N), 7.48 (d,
d 1H, Harom., J = 7.4, 4.9 Hz), 7.66–7.72 (m 1H, Harom., J = 7.8, 4.5 Hz), 8.00 (d, 1H,
Harom., J = 7.5 Hz), 8.10 (d, 1H, Harom., J = 7.8 Hz), 8.22 (d, 1H, Harom., J = 7.6 Hz),
8.40 (br, 1H, Harom.), 8.71 (d, 1H, Harom., J = 4.0 Hz), 8.88 (s, 1H, Harom), 11.12 (s, 1H,
D2O exchange, NH), 13C NMR (DMSO-d6) δ (ppm): 29.7 (CH2), 61.2 (CH), 122.9, 124.1,
124.4, 127.6, 130.7, 135.0, 135.8, 141.5, 148.3, 148.9, 153.4, 164.5 (C O), 169.6 (C O).
Anal. Calcd. for: C15H12N4O4S: C, 52.32; H, 3.51; N, 16.27; S, 9.31. Found: C, 52.24; H,
3.48; N, 16.11; S, 9.20.
N-(2-(4-Nitrophenyl)-4-oxothiazolidin-3-yl)nicotinamide (5j, Table 1)
IR (KBr): υ = 3110 (NH), 3034 (aromatic CH stretch.), 2928 (aliphatic CH stretch.),
1
1718 (C O), 1686 (C O), 1532 (C C) cm−1, H NMR (DMSO-d6) δ (ppm): 3.83 (d,
1H, CH2, J = 15.9 Hz), 3.99 (d, 1H, CH2, J = 16.00 Hz), 6.10 (s, 1H, S-CH-N), 7.50 (d, d
1H, Harom., J = 7.7, 4.9 Hz), 7.82 (d, 2H, Harom., J = 8.4 Hz), 8.10 (d, 1H, Harom., J = 7.7
Hz), 8.24 (d, 2H, Harom., J = 8.3 Hz), 8.71 (d, 2H, Harom., J = 4.4 Hz), 8.90 (s, 1H, Harom),
11.10 (br, 1H, D2O exchange, NH), 13C NMR (DMSO-d6) δ (ppm): 29.7 (CH2), 61.1 (CH),
124.2, 127.5, 129.2, 129.5, 135.9, 146.6, 148.2, 148.9, 153.4, 164.5 (C O), 169.6 (C O),
Anal. Calcd. for: C15H12N4O4S: C, 52.32; H, 3.51; N, 16.27; S, 9.31. Found: C, 52.04; H,
3.45; N, 16.16; S, 9.14.
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