Microwave-assisted one-pot three-component synthesis of thiazolidinones using KSF@Ni as an efficient heterogeneous catalyst

Article abstract of DOI:10.1080/17415993.2017.1343334

Convenient, one-pot three-component reaction for the synthesis of thiazolidinones from aldehydes, thiosemicarbazide, and maleic anhydride in the presence of KSF@Ni as heterogeneous catalyst under microwave irradiation was developed. Products were obtained

Full text of DOI:10.1080/17415993.2017.1343334

Journal of Sulfur Chemistry
ISSN: 1741-5993 (Print) 1741-6000 (Online) Journal homepage: http://www.tandfonline.com/loi/gsrp20
Microwave-assisted one-pot three-component
synthesis of thiazolidinones using KSF@Ni as an
efficient heterogeneous catalyst
Nosrat O. Mahmoodi, Samane Mohammadgholipour & Fateme Ghanbari
Pirbasti
To cite this article: Nosrat O. Mahmoodi, Samane Mohammadgholipour & Fateme Ghanbari
Pirbasti (2017): Microwave-assisted one-pot three-component synthesis of thiazolidinones
using KSF@Ni as an efficient heterogeneous catalyst, Journal of Sulfur Chemistry, DOI:
10.1080/17415993.2017.1343334
To link to this article: http://dx.doi.org/10.1080/17415993.2017.1343334
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Date: 29 June 2017, At: 12:08

JOURNAL OF SULFUR CHEMISTRY, 2017
https://doi.org/10.1080/17415993.2017.1343334
Microwave-assisted one-pot three-component synthesis of
thiazolidinones using KSF@Ni as an efficient heterogeneous
catalyst
Nosrat O. Mahmoodi, Samane Mohammadgholipour and Fateme Ghanbari Pirbasti
Department of Chemistry, Faculty of Science, University of Guilan, Rasht, Iran
ABSTRACT
ARTICLE HISTORY
Received 1 December 2016
Accepted 12 June 2017
Convenient, one-pot three-component reaction for the synthesis
of thiazolidinones from aldehydes, thiosemicarbazide, and maleic
anhydride in the presence of KSF@Ni as heterogeneous catalyst
undermicrowaveirradiationwasdeveloped. Productswereobtained
in reasonable yield in short reaction time.
KEYWORDS
KSF@Ni; multi-component
reaction; microwave
irradiation; antibacterial;
thiazolidinone
1. Introduction
The existence of heterocyclic compounds in pharmaceutical and natural products has
attracted great interest of organic chemists. Thiazolidinone derivatives are a class of hetero-
cyclic compound with diverse biological and pharmaceutical activities such as cytotoxicity
[1], antiproliferative and tumor inhibitory [2], antihyperglycemic [3], antifungal [4], anti-
toxoplasma gondii [5], antibacterial [6], anti-urease [7], antiviral [8], antischistosomal [9],
antimalarial [10], herbicidal [11], antidiabetic [12], anti-candida, and antioxidant activ-
ities [13]. Besides, thiazolidinones moieties are present in some drugs such as ralitoline
(anticonvulsant), etozoline (diuretic), and thiazolidomycin (active against streptomyces
species).
CONTACT Nosrat O. Mahmoodi
mahmoodi@guilan.ac.ir
Department of Chemistry, Faculty of Science,
University of Guilan, P.O. Box 41335-1914, Rasht, Iran
This article makes reference to supplementary material available on the publisher’s website at http://dx.doi.org/
10.1080/17415993.2017.1343334.
© 2017 Informa UK Limited, trading as Taylor & Francis Group

2
N. O. MAHMOODI ET AL.
Multicomponent reactions have gained a great deal of attention as they provide easy
and rapid access to a large, complex and diverse library of compounds without isolation
of any intermediate and have other advantages such as productivity, simple procedures,
convergence, time and energy saving, and high product yields. A survey of the litera-
ture showed that a number of research efforts have been devoted to multi-component
synthesis of thiazolidinones, e.g. synthesis of 2-hydrazolyl-4-thiazolidinones [14], 2-imino-
4-thiazolidinone [15], and spiro[indole-thiazolidinones] [16].
Recently, microwave irradiation has been used as an efficient energy source in many
chemical reactions [17–20]. The advantages of microwave-assisted synthesis are rate accel-
erations, high selectivity, improved yields, less by products, shorter reaction times, and
easier work-up.
Heterogeneous catalysts are widely used over homogenous catalysts due to their advan-
tages such as non-toxicity, easy of handling, storage safety, long-life times, safe, and easy
disposal, easy recovery by filtration and tolerance of a wide range of temperatures and
pressures. Montmorillonite KSF is a heterogeneous solid acid catalyst which has been used
widely in synthesis of coumarin-3-carboxylic acids [21], in the conversion of amines to N-
tert-butylcarbamates [22], in aza-Diels–Alder reactions of methylenecyclopropanes with
arenecarbaldehydes and arylamines [23], in the synthesis of coumarins via Pechmann reac-
tion [24], in the synthesis of 1,4-dioxo-3,4-dihydrophthalazine-2(1H)-carboxamides and
carbothioamides [25], and in the synthesis of 1,5-diaryl pyrazoles [26].
2. Results and discussion
2.1. Chemistry
Recently, we report various multi-component reactions efficiently catalyzed by metals sup-
ported on KSF [27–35]. In continuation of our previous reports, we investigated in this
report one-pot three-component synthesis of thiazolidinones catalyzed by the presence of
premade KSF@Ni (Scheme 1).
The FT-IR spectra of KSF and KSF@Ni are depicted in Figure 1. Ni–OH vibration
appeared at 3629 cm−1 and other vibrations, e.g. O–H, H–OH, Si–O, Si–O–Si appeared
at 3433, 1637, 1044, 526 and 466 cm−1, respectively [36] (Figure 1). The XRD patterns
of KSF@Ni indicated the diffraction peaks at 2θ = 18°, 35°, 45° and 55° that confirmed
translocation of Ni on KSF surface [37,38] (Figure 2).
Scheme 1. Synthesis of products 4a–j.

JOURNAL OF SULFUR CHEMISTRY
3
a
b
Figure 1. FT-IR spectra of KSF (a) and KSF@Ni (b).
The energy-dispersive X-ray (EDX) spectroscopy of KSF@Ni catalyst confirmed the
presence of the expected elements in the structure of the catalyst (Figure 3). As expected,
Si (66.26%) and Al (12.59%) are major elements that are the part of KSF and Ni (4.71%)
and confirms incorporation or adsorption of Ni on KSF.
To find the appropriate reaction conditions for synthesis of products 4a–j in the presence
of KSF@Ni, the one-pot three-component reaction of benzaldehyde 1i, thiosemicarbazide
2 and maleic anhydride 3 was selected as the model reaction. According to Table 1 entries
1–3, the model reaction preceded slowly under reflux condition in polar solvents, e.g.
EtOH, DMF, and MeOH. However, the product was obtained in shorter reaction time in
DMF (entry 2). The reaction occurred under microwave irradiation (70°C, 50 psi) in DMF
and toluene separately and also in mixtures of these solvents (entries 4–8). For example, a
mixture of DMF: toluene (1:1) led to the product in short reaction time (5 min) and high

4
N. O. MAHMOODI ET AL.
Figure 2. XRD spectra of KSF@Ni.
Figure 3. The EDX spectroscopy of the catalyst.
yield (60%) (entry 6). In another effort, the effect of the amount of the catalyst was investi-
gated (entries 9–12) the results showed that 0.03 g of catalyst gave the product in reasonable
yield and short reaction time (entry 6). Ultimately, the optimized reaction condition was
obtained as shown in entry 6, Table 1.
In addition, the recyclability and reusability of KSF@Ni as catalyst for preparation of
compound 4i was investigated (Table 2). The catalytic activity of KSF@Ni was restored
within the limit of catalyst amount for four runs. Furthermore, the amount of Ni in fresh
and reused catalyst was obtained as 14.917 and 2.315 mg/L, respectively according to ICP-
OES analysis.
Consequently, to investigate the generality of KSF@Ni as catalyst, different aldehydes
1a–j in the synthesis of 4a–j under optimized reaction condition were used (Table 3). As it
can be seen from Table 2, all aldehydes bearing electron withdrawing and electron releas-
ing groups reacted efficiently in short reaction times (3–5 min) and in high to good yields
(60–97%).

JOURNAL OF SULFUR CHEMISTRY
5
Table 1. Optimization of the synthesis of 4i.
Entry
Amount of catalyst (g)
Solvent
Condition
Time (min)
Yield (%)
1
2
3
4
5
6
7
8
0.03
0.03
0.03
0.03
0.03
0.03
0.03
0.03
0.01
0.02
0.04
–
EtOH
DMF
MeOH
DMF
Reflux
Reflux
Reflux
MW
420
300
540
12
15
5
6
5
10
8
8
40
48
38
50
47
60
52
56
48
50
48
35
Toluene
MW
DMF: Toluene (1:1)
DMF: Toluene (1:2)
DMF: Toluene (2:1)
DMF: Toluene (1:1)
DMF: Toluene (1:1)
DMF: Toluene (1:1)
DMF: Toluene (1:1)
MW (70°C, 50 psi)
MW (70°C, 50 psi)
MW (70°C, 50 psi)
MW (70°C, 50 psi)
MW (70°C, 50 psi)
MW (70°C, 50 psi)
MW (70°C, 50 psi)
9
10
11
12
50
Table 2. Recyclability of KSF@Ni.
Entry
Number of cycles
Time (min)
Yield (%)
1
2
3
4
1
2
3
4
7
10
10
14
56
51
46
40
Table 3. Synthesis of thiazolidinones 4a–j under optimized reaction condition.
Product
R
Time (min)
Yield (%)
m.p. (°C)
m.p. (°C)
4a
4b
4c
4d
4e
4f
4g
4h
4i
2,4-diCl
2,6-diCl
4-Cl
3-NO2
2-NO2
4-NO2
2-OH
4-OH
H
3
4
3
3
3
4
5
4
5
3
74
80
74
95
69
97
90
86
60
70
304–306
259–260
273–275
279–281
247–248
268–271
289–290
258–259
241–244
261–263
This work
This work
273–274 [39]
This work
This work
270–271 [39]
This work
This work
242–243 [39]
262–263 [39]
4j
4-OCH3
This work is similar to reported studies [14,39] that used p-TSOH as the catalyst in
the amounts of 0.2 and 0.01 mmol; however, in this one-pot 3MCRs recyclable KSF@Ni
was used as the heterogeneous catalyst (0.03 g). In addition, in the previous studies the
reaction time was reported as 5–12 and 10 min for the two steps with 33–82% and 33–76%
yields, respectively. In the present study, the reaction times were reduced to 3–5 min with
(60–97%) yields. Thus, KSF@Ni is an efficient catalyst for this procedure.
The structures of 4c, 4f, and 4i–j were confirmed using FT-IR spectra and by com-
parison with literature melting points. The structures of the products 4a–b, 4d–e, and
1
1
4g–h were characterized using FT-IR, H NMR, and 13C NMR spectra. The H NMR
spectral data were consistent with the expected structures as confirmed on the basis of
their chemical shifts, multiplicities, and coupling constants. The N–H and CO2H protons
−
appeared together as a broad signal at 12.71–11.88 ppm. Proton of the imine group CH N
appeared as a sharp singlet at 8.67–8.28 ppm and also aromatic protons were observed in
the expected chemical shift range of 8.59–6.83 ppm. Aliphatic protons of the CH–CH2
moiety appeared with diastereomeric multiplicities as expected due to the chiral carbon,

6
N. O. MAHMOODI ET AL.
Figure 4. Diastereomeric coupling of CH–CH2 moiety in products 4a–j.
the proton of chiral carbon appeared as the doublet of doublet at 4.48–4.33 ppm and also
diastereomeric protons appeared as the doublet of doublet at 3.09–2.85 ppm (Figure 4).
The 13C NMR spectra of 4a–b, 4d–e, and 4g–h were in agreement with their struc-
tures. Carbons of amide and carboxylic acid appeared at the low field at 176.0–175.6 and
−
−
172.2 ppm, respectively. Carbon of CH N and C N groups appeared at 167.2–160.4 and
158.8–151.3 ppm, respectively. Also, aromatic carbons were observed at 162.9–116.1 ppm
and aliphatic carbons were observed at 44.5–43.9 and 37.2–369 ppm.
2.2. Biology
In vitro antibacterial activity of compounds 4a–j was screened against Gram-positive and
Gram-negative bacterial strains including Staphylococcus aureus (S. aureus), Micrococcus
luteus (M. luteus), Escherichia coli (E. coli), and Pseudomonas aeruginosa (Ps. aeruginosa)
using the well-diffusion method. Tetracyline and Chloramphenicol were used as positive
controls. DMSO was used as a negative control and showed no activity against mentioned
bacterial strains. Also, the antibacterial activity of 4a–j was screened at the concentration
of 1000 μg/mL in DMSO. According to the results, none of the compounds inhibited E.
coli and Ps. aeruginosa. However, M. luteus and S. aureus were sensitive to the compounds
4g–h and 4b, respectively.
3. Conclusion
In conclusion, an efficient, convenient, high-yield procedure with a simple set up and
work up was reported for the one-pot three-component synthesis of thiazolidinones in the
presence of KSF@Ni as catalyst under microwave irradiation. The prepared catalyst was
confirmed using the FT-IR, XRD, ICP-OES and EDX analysis. Recyclability and reusabil-
ity of the catalyst, simple procedure, the use of low volume of solvents and short reaction
time are the prominent merits of this methodology.

JOURNAL OF SULFUR CHEMISTRY
7
4. Experimental
4.1. Material and instruments
Starting materials were obtained from Fluka and Merck. FT-IR spectra were measured with
a Shimadzu IR-470 spectrophotometer. The 1H NMR and 13C NMR spectra were obtained
on a Bruker Avance 400 and 100 MHz spectrometer, respectively. DMSO-d6 was used as
solvent. Melting points are uncorrected and were determined using MettlerFp5 apparatus.
XRD was recorded on Brucker AXS-D8 Advance instrument. MW apparatus model 2016
latest microwave synthesis manufactured by Zhengzhou Keda Machinery and Instrument
Equipment was used. KSF@Ni was prepared according to the literature using NiCl2 instead
of ZnCl2 [40]. Metal content of catalyst was analyzed using the SPECTRO ARCOS ICP-
OES analyzer. The chemical composition of catalyst was evaluated using Environmental
Scanning electron microscope equipped with an EDX instrument (Philips XL30).
4.2. General procedure for synthesis of 4a–j
Aldehyde 1 (1 mmol), thiosemicarbazide 2 (1.1 mmol), maleic anhydride 3 (5 mmol), and
KSF@Ni (0.03 g) were added to a mixture of DMF: Toluene 1:1 and was heated under
microwave irradiation (70°C, 50 psi) for the appropriate time (Table 3). The progress of
the reaction was monitored by TLC (n-hexane: EtOAc 4:3). After completion of the reac-
tion water was added to the mixture and the precipitated solid was filtered off and dried at
room temperature. The crude product was recrystallized from EtOH and the catalyst was
separated at this stage.
Spectral data are given below.
4.2.1. {2-[(2,4-Dichlorobenzylidene)hydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl}
acetic acid (4a)
White solid, Yield: 74%, m.p.: 304–306°C, FT-IR (ν, cm−1): 3444 (stretch, OH), 3100, 1733,
1687, 1619, 1582, 1329, 1227, 1253, 1051, 878, 785. 1H NMR (DMSO-d6, 400 MHz) δ: 12.68
(br. s, 1H, Ha or Hf ), 12.18 (br. s, 1H, Hf or Ha), 8.59 (s, 1H, Hh), 7.99 (d, J = 8.8 Hz, 1H,
Hj), 7.77 (d, J = 2.0 Hz, 1H, Hm), 7.55 (dd, J = 10.2, 2.1 Hz, 1H, H ), 4.41 (dd, J = 8.8,
4.0 Hz, 1H, H ), 3.04 (dd, Jsyn = 17.6, 3.6 Hz, 1H, Hc), 2.91 (dd, Jantki = 17.6, 8.8 Hz, 1H,
d
Hc ) ppm. 13C NMR (DMSO-d6, 100 MHz) δ: 175.9 (Ce), 172.2 (Cb), 167.0 (Cg), 151.3
ꢀ
(Ch), 136.2 (Ci), 134.7 (Cn), 130.7, 130.2, 129.2, 128.5 (Ck, Cl, Cj, Cm), 44.1 (Cd), 37.0 (Cc)
ppm. HRMS ((+)-ESI): m/z = 344.9749 (calcd. 344.9742 for C12H9Cl2N3O3S).
4.2.2. {2-[(2,6-Dichlorobenzylidene)hydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl}
acetic acid (4b)
White solid, Yield: 80%, m.p.: 259–260°C, FT-IR (ν, cm−1): 3443 (stretch, OH), 3018, 1722,
1636, 1584, 1332, 1220, 1258, 1034, 939, 848. 1H NMR (DMSO-d6, 400 MHz) δ: 12.58 (br.
s, 1H, Ha or Hf ), 12.27 (br. s, 1H, Hf or Ha), 8.56 (s, 1H, Hh), 7.59 (d, J = 8.0 Hz, 2H, Hk),
7.47 (t, J = 8.8 Hz, 1H, Hl), 4.39 (dd, J = 8.6, 3.8 Hz, 1H, Hd), 3.02 (dd, Jsyn = 17.6, 4.0 Hz,
1H, Hc), 2.92 (dd, Janti = 17.8, 8.6 Hz, 1H, Hc ) ppm. 13C NMR (DMSO-d6, 100 MHz)
ꢀ
δ: 176.0 (Ce), 172.2 (Cb), 167.2 (Cg), 152.1 (Ch), 134.5 (Cj), 131.9 (Ci), 130.4 (Cl), 129.7
(Ck), 44.1 (Cd), 36.9 (Cc) ppm. HRMS ((+)-ESI): m/z = 344.9738 (calcd. 344.9742 for
C12H9Cl2N3O3S).

8
N. O. MAHMOODI ET AL.
4.2.3. {2-[(4-Chlorobenzylidene)hydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl}acetic
acid (4c) [39]
White solid, Yield: 74%, m.p.: 273–275°C (obs. 273–274°C), FT-IR (ν, cm−1): 3444, 3093,
1734, 1686, 1627, 1588, 1329, 1222, 1255, 1090, 824. HRMS ((+)-ESI): m/z = 311.0126
(calcd. 311.0131 for C12H10ClN3O3S).
4.2.4. {2-[(3-Nitrobenzylidene)hydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl}acetic
acid (4d)
White solid, Yield: 95%, m.p.: 279–281°C, FT-IR (ν, cm−1): 3435, 3033, 1721, 1638, 1592,
1529, 1346, 1226, 1261, 736, 674. 1H NMR (DMSO-d6, 400 MHz) δ: 12.71 (br. s, 1H, Ha
or Hf ), 12.22 (br. s, 1H, Hf or Ha), 8.59–8.58 (m, 2H, Hh, Hn), 8.31 (ddd, J = 8.2, 2.2 Hz,
1H, Hj), 7.21 (td, J = 6.8, 1.2 Hz, 1H, Hl), 7.77 (t, J = 7.8 Hz, 1H, H ), 4.41 (dd, J = 8.6,
3.8 Hz, 1H, H ), 3.05 (dd, Jsyn = 17.6, 4.0 Hz, 1H, Hc), 2.93 (dd, Jantik = 17.8, 8.6 Hz, 1H,
d
Hc ) ppm. 13C NMR (DMSO-d6, 100 MHz) δ: 175.9 (Ce), 172.2 (Cb), 166.5 (Cg), 154.8
ꢀ
(Ch), 148.6 (Cm), 136.4 (Cj), 133.9 (Ci), 130.9 (Ck), 125.3 (Cl), 122.4 (Cn), 44.0 (Cd), 36.9
(Cc) ppm. HRMS ((+)-ESI): m/z = 322.0379 (calcd. 322.0372 for C12H10N4O5S).
4.2.5. {2-[(2-Nitrobenzylidene)hydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl}acetic
acid (4e)
White solid, Yield: 69%, m.p.: 247–248°C, FT-IR (ν, cm−1): 3445, 3101, 1734, 1686, 1621,
1581, 1529, 1347, 1248, 784, 747. 1H NMR (DMSO-d6, 400 MHz) δ: 12.74 (br. s, 1H, Ha or
Hf ), 12.16 (br. s, 1H, Hf or Ha), 8.67 (s, 1H, Hh), 8.08 (dd, J = 8.0, 1.2 Hz, 1H, Hn), 8.03
(dd, J = 7.6, 1.2 Hz, 1H, Hk), 7.83 (t, J = 7.4 Hz, 1H, Hm), 7.72 (dt, J = 7.7, 1.4 Hz, 1H,
Hl), 4.41 (dd, J = 8.8, 4.0 Hz, 1H, Hd), 3.04 (dd, Jsyn = 17.6, 4.0 Hz, 1H, Hc), 2.93 (dd,
Janti = 17.6, 8.8 Hz, 1H, Hc ) ppm. 13C NMR (DMSO-d6, 100 MHz) δ: 175.9 (Ce), 172.2
ꢀ
(Cb), 167.0 (Cg), 152.7 (Ch), 148.7 (Cj), 134.0 (Cm), 131.6 (C ), 129.4 (Cn), 128.8 (Ci),
125.1 (C ), 44.1 (C ), 36.9 (Cc) ppm. HRMS ((+)-ESI): m/z = l322.0367 (calcd. 322.0372
k
b
for C12H10N4O5S).
4.2.6. {2-[(4-Nitrobenzylidene)hydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl}acetic
acid (4f) [39]
White solid, Yield: 97%, m.p.: 268–271°C (obs. 270–271°C), FT-IR (ν, cm−1): 3419, 3043,
1715, 1639, 1604, 1571, 1524, 1341, 1269, 847. HRMS ((+)-ESI): m/z = 322.0378 (calcd.
322.0372 for C12H10N4O5S).
4.2.7. {2-[(2-Hydroxybenzylidene)hydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl}acetic
acid (4g)
White solid, Yield: 90%, m.p.: 289–290°C, FT-IR (ν, cm−1): 3443, 3051, 1731, 1636, 1336,
1215, 1268, 744. 1H NMR (DMSO-d6, 400 MHz) δ: 12.35 (br. s, 2H, Ha, Hf ), 10.8 (s, 1H,
Hk), 8.65 (s, 1H, Hh), 7.60 (dd, J = 8.0, 1.6 Hz, 1H, Ho), 7.35 (dt, J = 7.8, 1.7 Hz, 1H, Hm),
6.97–6.93 (m, 2H, Hl,Hn), 4.47 (dd, J = 8.6, 3.8 Hz, 1H, Hd), 3.06 (dd, Jsyn = 17.6, 4.0 Hz,
1H, Hc), 2.95 (dd, Janti = 17.6, 8.8 Hz, 1H, Hc ) ppm. 13C NMR (DMSO-d6, 100 MHz) δ:
ꢀ
175.6 (Ce), 172.2 (Cb), 164.0 (Cg), 158.5 (Ch), 158.2 (Cj), 132.6 (Cm), 131.1 (Co), 120.0
(Cn), 118.9 (Ci), 116.8 (Cl), 44.5 (Cd), 36.9 (Cc) ppm. HRMS ((+)-ESI): m/z = 279.0673
(calcd. 279.0678 for C12H13N3O3S).

JOURNAL OF SULFUR CHEMISTRY
9
4.2.8. {2-[(4-Hydroxybenzylidene)hydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl}acetic
acid (4h)
White solid, Yield: 86%, m.p.: 258–259°C, FT-IR (ν, cm−1): 3211, 1691, 1636, 1513, 1336,
1166, 1242, 832. 1H NMR (DMSO-d6, 400 MHz) δ: 12.57 (br. s, 1H, Ha or Hf ), 11.88 (br.
s, 1H, H or Ha), 10.0 (s, 1H, Hm), 8.28 (s, 1H, Hh), 7.60 (d, J = 6.8 Hz, 1H, Hj), 6.84
(dd, J = f8.8 Hz, 1H, H ), 4.35 (dd, J = 9.0, 3.8 Hz, 1H, H ), 3.02 (dd, Jsyn = 17.6, 4.4 Hz,
k
d
1H, Hc), 2.88 (dd, Janti = 17.6, 9.2 Hz, 1H, Hc ) ppm. 13C NMR (DMSO-d6, 100 MHz)
δ: 175.8 (Ce), 172.2 (Cb), 162.9 (Cl), 160.4 (Cg), 156.5 (Ch), 130.0 (Cj), 125.7 (Ci), 116.1
(Ck), 43.9 (Cd), 37.2 (Cc) ppm. HRMS ((+)-ESI): m/z = 293.0463 (calcd. 293.0470 for
C12H11N3O4S).
ꢀ
4.2.9. [2-(Benzylidenehydrazinylidene)-4-oxo-1,3-thiazolidin-5-yl]acetic acid (4i) [39]
White solid, Yield: 60%, m.p.: 241–244°C (obs. 242–243°C), FT-IR (ν, cm−1): 3422, 3033,
1712, 1640, 1335, 1255, 1261, 758, 689. m/z: 277.0521 Chemical Formula: C12H11N3O3S.
4.2.10. {2-[(4-Methoxybenzylidene)hydrazinylidene]-4-oxo-1,3-thiazolidin-5-yl}
acetic acid (4j) [39]
White solid, Yield: 70%, m.p.: 261–263°C (obs. 262–263°C), FT-IR (ν, cm−1): 3420,
3103, 2954, 2840, 1730, 1686, 1620, 1512, 1332, 1269, 1253, 829. HRMS ((+)-ESI):
m/z = 293.0840 (calcd. 293.0834 for C13H15N3O3S).
4.3. Antibacterial assay
The antibacterial activity of products 4a–j was investigated using a well-diffusion method.
Nutrient agar and nutrient broth cultures were prepared according to manufactures
instructions and were incubated at 37°C. The bacterial strains were prepared according to
0.5 McFarland standard. Thirty microliters of each bacterium was poured on each nutri-
ent agar plate and then wells with 5 mm diameter were cuts into agar plates using sterilized
glass tube. Each well received 30 μL of each compound (1000 compounds μg/ml in DMSO).
Then, the plates were incubated at 37°C for 24 h and the zone of inhibition was measured
and expressed in mm. Tetracycline and Chloramphenicol were used as positive controls
and DMSO was used as negative control.
Acknowledgements
The authors are grateful to the Research Council of University of Guilan for financial support of this
work.
Disclosure statement
No potential conflict of interest was reported by the authors.
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