Nano-CdZr4(PO4)6 as a reusable and robust catalyst for the synthesis of bis-thiazolidinones by a multicomponent reaction of aldehydes, ethylenediamine and thioglycolic acid

Article abstract of DOI:10.1080/17415993.2016.1267176

Nano-CdZr₄(PO₄)₆ has been used as an efficient catalyst for the preparation of bis-thiazolidinones by pseudo-five-component reaction of aldehydes, ethylenediamine and thioglycolic acid under reflux conditions in toluene. T

Full text of DOI:10.1080/17415993.2016.1267176

Journal of Sulfur Chemistry
ISSN: 1741-5993 (Print) 1741-6000 (Online) Journal homepage: http://www.tandfonline.com/loi/gsrp20
Nano-CdZr4(PO4)6 as a reusable and robust
catalyst for the synthesis of bis-thiazolidinones
by a multicomponent reaction of aldehydes,
ethylenediamine and thioglycolic acid
Javad Safaei-Ghomi, Seyed Hadi Nazemzadeh & Hossein Shahbazi-Alavi
To cite this article: Javad Safaei-Ghomi, Seyed Hadi Nazemzadeh & Hossein Shahbazi-
Alavi (2016): Nano-CdZr4(PO4)6 as a reusable and robust catalyst for the synthesis of bis-
thiazolidinones by a multicomponent reaction of aldehydes, ethylenediamine and thioglycolic
acid, Journal of Sulfur Chemistry, DOI: 10.1080/17415993.2016.1267176
To link to this article: http://dx.doi.org/10.1080/17415993.2016.1267176
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Date: 01 January 2017, At: 07:41

JOURNAL OF SULFUR CHEMISTRY, 2016
http://dx.doi.org/10.1080/17415993.2016.1267176
Nano-CdZr4(PO4)6 as a reusable and robust catalyst for the
synthesis of bis-thiazolidinones by a multicomponent
reaction of aldehydes, ethylenediamine and thioglycolic acid
Javad Safaei-Ghomi a, Seyed Hadi Nazemzadeha and Hossein Shahbazi-Alavia,b
aDepartment of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, Iran; bYoung
Researchers and Elite Club, Kashan Branch, Islamic Azad University, Kashan, Iran
ABSTRACT
ARTICLE HISTORY
Received 22 September 2016
Accepted 27 November 2016
Nano-CdZr4(PO4)6 has been used as an efficient catalyst for the
preparation of bis-thiazolidinones by pseudo-five-component reac-
tionofaldehydes, ethylenediamineandthioglycolicacidunderreflux
conditions in toluene. The present synthetic protocol has several
advantages, such as simplicity, excellent yields, short reaction times,
reusability of the catalyst and low catalyst loading.
KEYWORDS
Bis-thiazolidinones;
nano-CdZr4(PO4)6;
ethylenediamine; catalytic
activity; one-pot reaction
1. Introduction
Thiazolidinones are one of the biologically significant scaffolds due to their wide range
of biological and pharmaceutical properties, such as anti-leukemia [1], anti-inflammatory
and analgesic agents [2], antimicrobial [3], antitubercular [4], antiviral [5] and anti-HIV
[6,7] activities. Therefore, the development of efficient methods for the synthesis of thi-
azolidinones is of great interest. A few methods have been reported for the synthesis of
bis-thiazolidinones in the presence of such catalysts as HClO4–SiO2 [8], zeolite [9], ChCl
(choline chloride)/urea-based ionic liquid [10] and ZnCl2 [11]. However, some of the
reported methods have disadvantages, including long reaction times, harsh reaction condi-
tions, and use of toxic and non-reusable catalyst. Therefore, to avoid these limitations, the
CONTACT Javad Safaei-Ghomi
safaei@kashanu.ac.ir
Department of Organic Chemistry, Faculty of Chemistry,
University of Kashan, 51167 Kashan, Iran
Supplemental data for this article can be accessed here. http://dx.doi.org/10.1080/17415993.2016.1267176
© 2016 Informa UK Limited, trading as Taylor & Francis Group

2
J. SAFAEI-GHOMI ET AL.
Scheme 1. Synthesis of bis-thiazolidinones using nano-CdZr4(PO4)6.
exploration of an efficient and reusable catalyst for the preparation of bis-thiazolidinones
is still favored. The feasibility of accomplishing one-pot multicomponent synthesis in the
presence of nanoheterogeneous catalyst could improve the reactions rates and shorten
the reactions times [12–14]. Further, the reusability of the catalyst has become a con-
siderable trend in chemistry owing to increasing environmental and economic concerns.
Nanocatalysts are recovered and separated through centrifugation or filtration, and are
acknowledged to possess a comprehensive range of special characterizations, such as high
stability, excellent activity, good recovery and efficient recyclability [15,16]. Nanocrys-
talline structures are utilized as the convenient and efficient catalysts in many organic
reactions due to their high surface-to-volume ratio and coordination parts, which provide
a large number of active sites per unit area. For this reasons, nanocatalysts are particu-
larly well suited for the synthesis of bioactive compounds. In continuation of our previous
investigations in the applications of heterogeneous catalysts for the synthesis of biological
heterocyclic compounds [17–19], we wish to report the synthesis of bis-thiazolidinones by
one-pot pseudo-five-component condensation of araldehydes, ethylenediamine and thio-
glycolic acid with nano-CdZr4(PO4)6 as a retrievable and robust heterogeneous catalyst
under reflux conditions in toluene (Scheme 1).
2. Results and discussion
We initially attempted a pseudo-five-component condensation of 4-chlorobenzaldehyde
(2 mmol), ethylenediamine (1 mmol) and thioglycolic acid (2 mmol) as a model reaction
in different conditions. Yields were determined in the presence of CaO NPs, CuO NPs,
SnO NPs, ZrO2 NPs and nano-CdZr4(PO4)6 and the results are given in Table S1 (Entries
2–12) of electronic supplementary information. Nano-CdZr4(PO4)6 gave the best yields
in the shortest time and a very good yield of 88% was obtained with 0.6 mol%, which was
not improved by increasing to 0.8 mol%. A reaction run in the absence of any catalyst gave
a yield of only 9% (Entry 1).
With the optimal conditions in hand, we turned to explore the efficacy of the
catalyst using different aromatic aldehydes and the results are given in Table 1.
We found that our method is compatible with diverse aromatic aldehydes, such as
4-chlorobenzaldehyde, 4-methyl-benzaldehyde, 4-nitro-benzaldehyde, picolinaldehyde

a
Table 1. Synthesis of bis-thiazolidinones using nano-CdZr4(PO4)6 .
Entry
1
Aldehyde
Product
Time (min)
80
Yield (%)
88
M.p. (°C)
M.p. (°C) found
150–152
285–288 [20]
2
90
81
–
158–160
3
85
84
152–155 [8]
155–157
(continued).

Table 1. Continued.
Entry
4
Aldehyde
Product
Time (min)
80
Yield (%)
89
M.p. (°C)
–
M.p. (°C) found
164–166
5
85
86
–
222–224
6
82
86
167–169 [21]
170–172
7
85
85
198–200 [21]
191–193

8
82
80
90
86
86
80
224–225 [21]
210–211 [20]
–
221–223
143–145
163–165
9
10
aIsolated yield.

6
J. SAFAEI-GHOMI ET AL.
and 4-isopropylbenzaldehyde. A variety of aromatic aldehydes, including ortho, meta and
para-substituted aryl aldehydes, were isolated in good to excellent yields under reflux con-
ditions in toluene. Aromatic aldehydes with electron-withdrawing groups reacted faster
than those with electron-donating groups. It has been observed that better yields are
achieved with substrates having electron-withdrawing groups.
Owing to the presence of 2 and 2ꢀ equivalent stereogenic centers, bis-thiazolidinones can
be obtained as rac. 2R,2ꢀR/2S,2ꢀS and 2R,2ꢀS-meso isomers. These bis-thiazolidinones have
been obtained, as previously reported, by the reaction of mercaptoacetic acid with N,Nꢀ-
dibenzylidenethylendiamines [20,22]. After workup, the crude mixture of isomers was
separated by silica gel column chromatography (diethyl ether/petroleum ether in variable
ratio mixtures). In general meso isomers eluted more slowly than corresponding race-
mates. The racemate isomer 4f was obtained in higher yields than meso isomer 4f (58%
for the rac. isomer 4f and 38% for the meso isomer 4f). According to the GC–MS anal-
ysis made to the compound 4f, there are two chromatographic peaks with almost equal
retention times, which are the sign of corresponding racemate (2R,2ꢀR/2S,2ꢀS) and meso-
form (2R,2ꢀS-meso), as has been already proved. But not only the bis-thiazolidinone 4f
showed diastereoisomeric presence, the GC analysis of 4a–4j exhibits broad chromato-
graphic peaks, typical for overlapped peaks with very similar retention times. We were
unable to separate these mixtures of isomers by conventional column chromatography. The
1H NMR spectra of the compounds 4a–4j displayed a doublet of doublets at δ 3.80–3.95
ppm due to the methylene proton HA at C–5 (–CO–CHAHB–S) because of its interac-
tion with the geminal proton HB at C–5 (–CO–CHAHB–S) and the proton at the chiral
C-2 (S–CHAr–N); doublet of doublets at δ 3.50–3.75 ppm due to the methylene proton
HB at C–5 (–CO–CHAHB–S) because of its interaction with the geminal proton HA
(–CO–CHAHB–S) and a diastereotopic proton Ha (–N–CHaHb–CHaCHb–N–) of the
ethylene fragment. This last proton Ha (–N–CHaHb–CHaCHb–N–) displayed a doublet
of doublets or a multiplet at δ 2.50–2.85 ppm because of its interaction with the germi-
nal proton Hb (–N–CHaHb–CHaCHb–N–) and the proton HB (–CO–CHAHB–S) at
the C–5. The Hb proton (–N–CHaHb–CHaCHb–N–) at the aliphatic chain suffered the
anisotropic effect from the near amide group or aryl substituents and it went to down field
at d 3.35–4.0 ppm appearing overlapped with HB or HA (–CO–CHAHB–S) as a multi-
plet. These germinal protons of each methylene group reside in magnetic non-equivalent
environments [20–22].
The reusability of CdZr4(PO4)6 nanoparticles was also examined. After completion of
the reaction, CHCl3 was added to dilute the reaction mixture after terminating the reaction.
The catalyst was insoluble in the solvent and was separated by centrifuging. The reusability
of the catalyst was investigated for seven runs, providing almost analogous yields of the
favorable product (Figure 1S of Electronic supplementary information)).
A probable mechanism for the synthesis of bis-thiazolidinone derivatives using nano-
CdZr4(PO4)6 is shown in Scheme 2. A proposed mechanism is outlined via primary imine
intermediate formation followed by an attack of the sulfur atoms of the thioglycolic acids
on the activated imine groups followed by intramolecular cyclization with the elimination
of H2O giving rise to the cyclized product bis-thiazolidinones. In this mechanism, the sur-
=
=
face atoms of CdZr4(PO4)6 nanoparticles activate the C O, C N, S–H groups for better
reaction with nucleophiles. These surface atoms act as the centers where chemical reactions
could be catalytically spurred (Scheme 2).

JOURNAL OF SULFUR CHEMISTRY
7
Scheme 2. Proposed reaction pathway for the synthesis of bis-thiazolidinones.
3. Conclusions
In conclusion, we have developed a simple and highly efficient protocol for the synthesis
of bis-thiazolidinones by one-pot pseudo-five-component condensation of araldehydes,
ethylenediamine and thioglycolic acid with nano-CdZr4(PO4)6 as a retrievable and robust
heterogeneous catalyst under reflux conditions in toluene. High yields, short reaction
times, atom economy, reusability of the catalyst and low catalyst loading are some of the
remarkable advantages of the present protocol.
4. Experimental design
4.1. Materials and apparatus
Reagent-grade chemicals and solvents were purchased from Sigma-Aldrich or Merck
and were used without further purification. NMR spectra were obtained on a Bruker

8
J. SAFAEI-GHOMI ET AL.
Avance-400 MHz spectrometer (1H NMR at 400 Hz, 13C NMR at 100 Hz) in DMSO-d6
or CDCl3 using tetramethylsilane as an internal standard. Chemical shifts (δ) are given in
ppm and coupling constants (J) are given in Hz. The infrared (IR) spectra were recorded
on FT-IR Magna 550 apparatus using with KBr plates. Melting points were determined
on Electro thermal 9200, and are not corrected. The elemental analyses (C, H, N) were
obtained from a Carlo ERBA Model EA 1108 analyzer. Powder X-ray diffraction was car-
ried out on a Philips diffractometer of X’pert Company with monochromatized Zr Kα
radiation (λ = 1.5406 Å). In order to study the particle size and morphology of the syn-
thesis nano-CdZr4(PO4)6, field emission scanning electron microscopy (FE-SEM) images
of the products were visualized by a HITACHI S4160 FE-SEM.
4.1.1. Preparation of nanocrystalline CdZr4(PO4)6 ceramics
Nanocrystalline nano-CdZr4(PO4)6 ceramics were prepared according to the technique
reported in the literature [23] (See Electronic supplementary information).
4.1.2. General procedure for the preparation of bis-thiazolidinones
A mixture of aldehydes (2 mmol), ethylenediamine(1 mmol), thioglycolic acid (2 mmol)
and 0.6 mol% of nano-CdZr4(PO4)6 in toluene (5 mL) was refluxed. The reaction was
monitored by thin-layer chromatography. After completion of the reaction, CHCl3 was
added to dilute the reaction mixture after terminating the reaction. The catalyst was
insoluble in the solvent and was separated by centrifuging. The CHCl3 was evapo-
rated and the crude mixture was separated by silica gel column chromatography (diethyl
ether/petroleum ether to get pure product).
4.1.3. Spectral data
4.1.3.1. 3,3ꢀ-(ethane-1,2-diyl)bis(2-(4-chlorophenyl)thiazolidin-4-one)(4a). White solid;
1
m.p.150–152°C, IR (KBr) cm−1: 2941, 1661; H NMR (400 MHz, DMSO-d6): δ (ppm):
2.51–2.57 (m, 2H), 3.39–3.44 (m, 2H), 3.51 (d, J = 15 Hz, 2H), 3.71 (dd, J = 1.7, 15 Hz,
2H), 5.83 (d, J = 1.4 Hz, 2H), 7.16 (d, J = 7 Hz, 4H), 7.36 (d, J = 7 Hz, 4H);13C NMR
(100 MHz, DMSO-d6): δ (ppm): 31.7, 40.2, 62.9, 128.2, 130.5, 131.4, 141.2, 170.8; Anal.
calcd for C20H18Cl2N2O2S2: C, 52.98; H, 4.00; N, 6.18; S, 14.14; Found: C, 52.79; H, 4.22;
N, 6.18; S, 14.07.
4.1.3.2. 3,3ꢀ-(ethane-1,2-diyl)bis(2-(p-tolyl)thiazolidin-4-one) (4b). White solid; m.p.
1
158–160°C, IR (KBr) cm−1: 2929, 1669; H NMR (400 MHz, CDCl3): δ (ppm): 2.28 (s,
6H), 2.68–2.75 (m, 2H), 3.53–3.61 (m, 4H), 3.67 (dd, J = 1.8, 16 Hz, 2H), 5.46 (d, J = 1.5
Hz, 2H), 7.11 (s, 8H);13C NMR (100 MHz, CDCl3): δ (ppm): 20.8, 32.1, 39.5, 63.2, 126.7,
129.3, 135.3, 138.9, 171.1; Anal. calcd for C22H24N2O2S2: C, 64.05; H, 5.86; N, 6.79; S,
15.54; Found: C, 63.95; H, 5.92; N, 6.84; S, 15.31.
4.1.3.3. 3,3ꢀ-(ethane-1,2-diyl)bis(2-phenylthiazolidin-4-one) (4c). White solid; m.p.
1
155–157°C, IR (KBr) cm−1: 2923, 1660; H NMR (400 MHz, DMSO-d6): δ (ppm):
2.52–2.58 (m, 2H), 3.41–3.47 (m, 2H), 3.52 (d, J = 16 Hz, 2H), 3.72 (dd, J = 1.8, 16 Hz,
2H), 5.59 (d, J = 1.6 Hz, 2H), 7.19–7.33 (m, 10H);13C NMR (100 MHz, DMSO-d6): δ
(ppm): 32.3, 41.2, 62.8, 127.1, 127.3, 128.6, 140.4, 171.4; Anal. calcd for C20H20N2O2S2: C,
62.47; H, 5.24; N, 7.29; S, 16.68; Found: C, 62.35; H, 5.17; N, 7.18; S, 16.57.

JOURNAL OF SULFUR CHEMISTRY
9
4.1.3.4. 3,3ꢀ-(ethane-1,2-diyl)bis(2-(4-nitrophenyl)thiazolidin-4-one) (4d). Yellow solid;
1
m.p.164–166°C, IR (KBr) cm−1: 2935, 1670, 1521; H NMR (400 MHz, DMSO-d6): δ
(ppm): 2.64–2.73 (m, 2H), 3.53–3.62 (m, 2H), 3.67–3.73 (m, 2H), 3.92 (dd, J = 1.9, 16
Hz, 2H), 6.03 (d, J = 1.9 Hz, 2H), 7.46 (d, J = 8 Hz, 4H), 8.07 (d, J = 8 Hz, 4H);13C NMR
(100 MHz, DMSO-d6): δ (ppm): 32.7, 41.6, 63.4, 123.9, 130.1, 147.2, 150.2, 171.6; Anal.
calcd for C20H18N4O6S2: C, 50.62; H, 3.82; N, 11.81; S, 13.51; Found: C, 50.53; H, 3.79; N,
11.65; S, 13.42.
4.1.3.5. 3,3ꢀ-(ethane-1,2-diyl)bis(2-(3-nitrophenyl)thiazolidin-4-one) (4e). Cream solid;
1
m.p. 222–224°C, IR (KBr) cm−1: 2932, 1663, 1516; H NMR (400 MHz, DMSO-d6): δ
(ppm): 2.63–2.69 (m, 2H), 3.53–3.59 (m, 2H), 3.62–3.68 (m, 2H), 3.88 (dd, J = 1.7, 15 Hz,
2H), 5.95 (d, J = 1.9 Hz, 2H), 7.53–7.72 (m, 4H), 8.01–8.09 (m, 4H); 13C NMR (100 MHz,
DMSO-d6): δ (ppm): 32.4, 41.4, 63.1, 126.2, 129.4, 130.8, 134.1, 143.9, 148.4, 171.5; Anal.
calcd for C20H18N4O6S2: C, 50.62; H, 3.82; N, 11.81; S, 13.51; Found: C, 50.54; H, 3.69; N,
11.75; S, 13.46.
4.1.3.6. 3,3ꢀ-(ethane-1,2-diyl)bis(2-(pyridin-2-yl)thiazolidin-4-one) (4f). Cream solid;
m.p. 170–172°C, IR (KBr) cm−1: 2937, 1674; 1H NMR (400 MHz, CDCl3): δ (ppm): 2.66
(dd, J = 8, 18 Hz, 2H), 3.53–3.59 (m, 2H), 3.73–3.80 (m, 2H), 3.91 (dd, J = 8, 18 Hz, 2H),
5.81 (d, J = 1.2 Hz, 2H), 7.17 (dd, J = 5, 8 Hz, 2H), 7.20 (d, J = 10 Hz, 2H), 7.62 (ddd,
J = 2, 8, 10 Hz, 2H), 8.49 (d, J = 5 Hz, 2H);13C NMR (100 MHz, CDCl3): δ (ppm): 32.9,
40.1, 63.3, 121.1, 123.5, 138.1, 150.5, 158.4, 171.5; Anal. calcd for C18H18N4O2S2: C, 55.94;
H, 4.69; N, 14.50; S, 16.59; Found: C, 55.85; H, 4.70; N, 14.43; S, 16.75.
4.1.3.7. 3,3ꢀ-(ethane-1,2-diyl)bis(2-(pyridin-3-yl)thiazolidin-4-one) (4g). White solid;
m.p. 191–193°C, IR (KBr) cm−1: 2931, 1668; 1H NMR (400 MHz, DMSO-d6): δ (ppm):
2.68 (dd, J = 6 Hz, 15, 2H), 3.49 (dd, J = 6, 15 Hz, 2H), 3.62 (d, J = 16 Hz, 2H), 3.9
(dd, J = 1.9, 16 Hz, 2H), 5.78 (d, J = 1.7 Hz, 2H), 7.35–7.41 (m, 2H), 7.75–7.81 (m, 2H),
8.51–8.58 (m, 4H); 13C NMR (100 MHz, DMSO-d6): δ (ppm): 32.1, 39.6, 61.4, 130.2, 134.8,
135.1, 148.5, 150.2, 171.1; Anal. calcd for C18H18N4O2S2: C, 55.94; H, 4.69; N, 14.50; S,
16.59; Found: C, 55.83; H, 4.77; N, 14.43; S, 16.67.
4.1.3.8. 3,3ꢀ-(ethane-1,2-diyl)bis(2-(pyridin-4-yl)thiazolidin-4-one) (4h). White solid;
m.p. 221–223°C, IR (KBr) cm−1: 2934, 1667; 1H NMR (400 MHz, DMSO-d6): δ (ppm):
2.66 (dd, J = 6, 15 Hz, 2H), 3.56–3.63 (m, 4H), 3.82 (dd, J = 1.6, 16 Hz, 2H), 5.72
(d, J = 1.4 Hz, 2H), 7.31 (d, J = 5 Hz, 4H), 8.51 (d, J = 5 Hz, 4H);13C NMR (100
MHz, DMSO-d6): δ (ppm): 32.2, 40.3, 61.7, 121.1, 148.7, 149.8, 171.4; Anal. calcd for
C18H18N4O2S2: C, 55.94; H, 4.69; N, 14.50; S, 16.59; Found: C, 55.95; H, 4.71; N, 14.54; S,
16.55.
4.1.3.9. 3,3ꢀ-(ethane-1,2-diyl)bis(2-(2-chlorophenyl)thiazolidin-4-one)(4i). White solid;
1
m.p.143–145°C, IR (KBr) cm−1: 2938, 1663; H NMR (400 MHz, CDCl3): δ (ppm):
2.48–2.53 (m, 2H), 3.34–3.4 (m, 2H), 3.43–3.49 (m,2H), 3.67 (dd, J = 1.6, 16 Hz, 2H), 5.77
(d, J = 1.4 Hz, 2H), 7.13–7.21 (m, 6H), 7.63 (dd, J = 2, 5 Hz, 2H);13C NMR (100 MHz,
CDCl3): δ (ppm): 31.7, 39.5, 62.2, 124.4, 125.3, 126.4, 128.1, 128.9, 135.1, 170.8; Anal. calcd

10
J. SAFAEI-GHOMI ET AL.
for C20H18Cl2N2O2S2: C, 52.98; H, 4.00; N, 6.18; S, 14.14; Found: C, 53.65; H, 4.12; N, 6.07;
S, 14.03.
4.1.3.10. 3,3ꢀ-(ethane-1,2-diyl)bis(2-(4-isopropylphenyl)thiazolidin-4-one) (4j). White
solid; m.p. 163–165°C, IR (KBr) cm−1: 2955, 1661; 1H NMR (400 MHz, CDCl3): δ (ppm):
1.17 (d, J = 7 Hz, 12H), 2.69–2.78 (m, 2H), 2.80–2.89 (m, 2H), 3.55–3.64 (m, 4H), 3.68
(dd, J = 1.8, 16 Hz, 2H), 5.48 (d, J = 1.4 Hz, 2H), 7.13 (d, J = 8 Hz, 4H), 7.16 (d, J = 8
Hz, 4H);13C NMR (100 MHz, CDCl3): δ (ppm): 23.4, 32.2, 33.4, 39.6, 63.1, 126.6, 126.7,
135.6, 149.8, 171.1; Anal. calcd for C26H32N2O2S2: C, 66.63; H, 6.88; N, 5.98; S, 13.68;
Found: C, 66.43; H, 6.78; N, 6.07; S, 13.55.
Acknowledgements
Authors are grateful to Dr Shayesteh Asadollahi for his help.
Disclosure statement
No potential conflict of interest was reported by the authors.
Funding
The authors are grateful to University of Kashan for supporting this work by Grant NO:
159196/XXII.
ORCID
Javad Safaei-Ghomi http://orcid.org/0000-0002-9837-4478
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DOI:10.1007/s11164-016-2608-6