Cu(i)-catalyzed microwave-assisted synthesis of 1,2,3-triazole linked with 4-thiazolidinones: A one-pot sequential approach

Article abstract of DOI:10.1039/c4ra12592d

A novel copper(i) catalyzed, microwave-assisted one-pot, four-component sequential reaction between a propargyloxybenzaldehyde, a substituted phenyl azide, a substituted aniline and thioglycolic acid has been developed for the synthesis of 3-phenyl-2-[4-{

Full text of DOI:10.1039/c4ra12592d

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Cu(I)-Catalyzed Microwave-Assisted Synthesis of 1,2,3-triazole linked with 4-
thiazolidinones : A one-pot sequential approach
a, b
a
a
a, b
Yogesh Kumar, Akanksha Matta, Prashant Kumar, Virinder S. Parmar, Erik V. Van der
b
, a
Eycken and Brajendra K. Singh*
[
[
a] Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India
Eꢀmail: singhbk@chemistry.du.ac.in
b] Laboratory for Organic & MicrowaveꢀAssisted Chemistry (LOMAC), Department of
Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Bꢀ3001 Leuven,
Belgium
Abstract:
N
N
N
OH
HS
S
O
N3
N
N
O
CuSO 5H O
D-Glucose
4.
2
O
N
6
N
R1
O
O
R1
+
THF/H O
NH2
2
OHC
R1
5 (a-c)
2 : 1
CHO
3
8
(a-d')
R2
Intermediate
R2
7
(a-i)
A novel copper (I) catalyzed, microwaveꢀassisted oneꢀpot, fourꢀcomponent sequential reaction
between a propargyloxybenzaldehyde, a substituted phenyl azide, a substituted aniline and
thioglycolic acid has been developed for the synthesis of 3ꢀphenylꢀ2ꢀ[4ꢀ{(1ꢀphenylꢀ1Hꢀ1,2,3ꢀ
triazolꢀ4ꢀyl)methoxy}phenyl]thiazolidinꢀ4ꢀones.
Keywords: Thiazolidinones / Triazoles / Microwaveꢀassisted synthesis / Cu(I) catalysis / Oneꢀ
pot sequential synthesis

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Introduction
Thiazolidinones and 1,2,3ꢀtriazoles represent important classes of drugs in medicinal chemistry.
They are among the most extensively investigated compounds by biochemists and medicinal
1
2
3
4
chemists. Thiazolidinones in particular show interesting anticancer, antiꢀHIV, antimalarial,
5
6
7
8
9
tuberculostatic, antihistaminic, anticonvulsant, antibacterial and antiarrythmic activities.
1
0
11
12
Similarly, various triazole derivatives possess antifungal, anticancer, antituberculosis and
1
3
antimicrobial activities.
So called hybrid molecules have been shown to be highly active and effective in medicinal
chemistry. Synergistic effects are obtained via hybridization of two different bioactive moieties
1
4
with complementary pharmacophoric functions, or with different modes of action. The
confirmation of this hypothesis has been well established in previous studies of 4ꢀthiazolidinones
1
5
coupled with other heterocyclic fragments, i. e. resulting in high antitumor activity. As a result,
we have planned the synthesis of linked thiazolidinoneꢀtriazole hybrid molecules. 4ꢀ
Thiazolidinones have been conveniently synthesized by a threeꢀcomponent condensation of a
1
5
primary amine, an aldehyde, and either a mercaptoacetic or mercaptopropanoic acid. This
1
6
cyclocondensation could be accelerated with N,N'ꢀ dicyclohexylcarbodiimide (DCC), 2ꢀ(1Hꢀ
1
7
18
benzotriazoleꢀ1ꢀyl)ꢀ1,1,3,3ꢀtetramethyluronium hexafluorophosphate (HBTU),
γꢀferrite,
1
9
20
21
22
ZnCl2, sodium sulfate, [bmim][PF6], and activated fly ash. The use of microwave
2
3
24
irradiation and polymer supported systems has also been reported. However, the main
bottleneck of these protocols is mostly harsh reaction conditions, prolonged heating, and the
need for simultaneous removal of water to accelerate the cyclocondensation. On the other hand,
2
5
the synthesis of 1,2,3ꢀtriazoles has been reported by various methods, like copperꢀcatalyzed
2
6
azideꢀalkyne cycloaddition (CuAAC) reaction and microwaveꢀassisted oneꢀpot reaction of an
2
7
alkyl halide, sodium azide and an alkyne. We have recently reported the formation of 1,2,3ꢀ

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2
8
triazoles using Dꢀglucose as a reducing agent for the copper catalyst. Very recently, metal free
2
9
synthesis of 1,2,3ꢀtriazoles has been also developed.
Microwave irradiation is an alternative heating technique based on the transformation of
3
0
electromagnetic energy into heat. Often this method increases the rate of chemical reactions
and results in higher yields.
2
8b, 31
In recent years, multicomponent reactions (MCRs)
have received increasing attention due to
their simplicity, efficiency, atom economy, shortened reaction times, and the possibility for
diversityꢀoriented synthesis. The combination of MCRs with transition metalꢀcatalysis gives
access to complex molecules in few steps as compared to traditional multistep processes. We
have investigated the application of microwave irradiation for the synthesis of our hybrid
molecules.
Results and Discussion
In view of the useful applications of 4ꢀthiazolidinones and 1,2,3ꢀtriazoles, we have developed a
new microwaveꢀassisted Cu(I)ꢀcatalyzed oneꢀpot, two step sequential synthesis via reaction of an
propargyloxybenzaldehyde, an aryl azide, an aniline and thioglycolic acid under microwave
irradiation. This synthesis could be achieved by three different pathways A, B and C (Scheme 1).
The simple one could be a twoꢀstep synthesis where either triazole ring formation takes place,
followed by the thiazolidinone ring (Path A) or vice versa, i.e. formation of the thiazolidinone
ring followed by the triazole ring (Path B). However, alternatively, oneꢀpot, twoꢀstep synthesis
could be employed, where initially 4ꢀ(propꢀ2ꢀynꢀ1ꢀyloxy)benzaldehyde and an aryl azide are
reacted followed by addition of the aniline and thioglycolic acid, to form the desired hybrid
molecule (Path C). Interesting to mention here that the second step where aniline and

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thioglycolic acid react with triazolyated intermediate didn’t proceed under conventional heating.
Moreover, attempt to succeed this reaction in a single step, oneꢀpot manner was not feasible even
under microwave irradiation in contrast to the sequential addition of the reactants as shown in
Path C (Scheme 1).
N3
CHO
NH2
O
CuSO 5H O
4
.
2
D-Glucose
OH
+
+
+
O
HS
Path A
N
N
THF:H O,
2
N
O
MW
CHO
Yield = 93 %
Yield = 30 %
Toluene,
MW
overall yield = 28 %
OH
HS
N
N
O
S
N
N
O
N3
N
N
O
CuSO 5H O
4
.
2
H N
2
N
D-Glucose
O
O
Path C
+
THF : H O
Temp. 70 oC,
2
Yield = 75 %
OHC
CHO
MW
Intermediate
Pmax 100W
Time 40-50 min
CuSO 5H O
Yield = 75 %
4
.
2
D-Glucose
overall yield = 25 %
THF:H O,
2
MW
O
NH2
S
Toluene,
MW
N3
OH
O
Path B
+
HS
+
N
+
O
O
CHO
Yield = 33 %
Scheme 1. Synthesis of thiazolidinone linked triazole
Our initial investigation was focused on the screening of various solvents to achieve the best
yield under microwave irradiation (Table 1). The reaction was unsuccessful when carried out
in polar aprotic solvents like tetrahydrofuran (THF), acetonitrile (MeCN), 1,4ꢀdioxane and
non polar aprotic solvent like toluene, while the reaction went to completion when carried out
in polar protic solvents, like ethanol (EtOH) and methanol (MeOH) resulting in the formation
of the desired product in 33% and 29% yield, respectively (Table 1, entries 5 and 6). To our
delight, when the reaction was carried out in an aqueous mixture of toluene or THF, decent

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amounts of compound 8a were obtained (Table 1, entries 7 and 8). The reaction did not run
to completion when it was carried out in chloroform or dioxane mixed with water (Table 1,
entries 9 and 10). Among the screened aqueous solvent, THF/H O (2:1) appeared to be the
2
most effective (Table 1, entry 8).
a
Table 1: Optimization of the solvent system.
O
OH
Br
2
K2CO3
DMF, RT
CHO
3
CHO
N
N
N
1
. CuSO 5H O,
4. 2
D-Glucose
Solvent
1
S
O
N
O
2
. Thioglycolic acid, (6)
Aniline (7a)
MW, 100W
NH2
N3
8a
1
) NaNO + HCl
2
o
0
-5 C, 1h
2
) NaN , RT, 2h
3
5a
4a
o
b
Entry
Solvent
Temp. ( C)
Time (min)
Ist step + 2nd step
20 + 35
Yield (%)
1
2
3
4
Toluene
THF
110
70
c
c
c
c
20 + 25
MeCN
100
100
20 + 30
1,4ꢀdioxane
5 + 10

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5
6
7
8
9
1
EtOH
85
80
90
70
50
100
75
15 + 55
5 + 40
33
29
50
75
c
MeOH
Toluene/H O, (2:1)
5 + 35
2
THF/H O, (2:1)
15 + 40
10 + 30
10 + 30
15 + 70
2
CHCl /H O, (2:1)
3
2
0
1
Dioxane/H O, (2:1)
c
2
1
MeCN/H O, (2:1)
17
2
a
The first step involves the reaction of 4ꢀ(propꢀ2ꢀynꢀ1ꢀyloxy)benzaldehyde (3) (1.8 mmol), phenyl azide (5a)
2.2 mmol), CuSO .5H O (0.35 mmol) and Dꢀglucose (0.75 mmol) in different solvents under microwave
(
4
2
irradiation for the indicated time and temperature at 100 W maximum power, followed by the addition of aniline
b
(
7a) (2.2 mmol) and thioglycolic acid (6) (2.2 mmol) in the second step; isolated yields, c = no reaction
To investigate the scope and limitations, various phenyl azides 5a-c and anilines 7a-i were
evaluated employing the optimized conditions. All the screened azides and anilines reacted
smoothly with propargyloxybenzaldehyde (3) and thioglycolic acid (6) and afforded the
expected desired products 8 (a-d') (Table 2) in good yields. Anilines bearing either an
electron donating group or electron withdrawing group were well tolerated.
Table 2: Scope and limitations of the protocol employing different phenyl azides 5a-c
a
and anilines 7a-i.

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1
2
Entry
Compd.
R
R
Time (min)
Yield
c
b
nd
(%)
(
I step) + II step
st
1
2
3
4
5
6
7
8
9
8a
8b
8c
8d
8e
8f
H
H
40
50
45
40
40
40
40
45
40
45
50
40
75
82
76
75
84
82
76
62
71
85
69
74
H
H
H
H
H
H
H
H
4ꢀCOCH3
3ꢀCOCH3
4ꢀCH3
3ꢀCH3
4ꢀOCH3
2ꢀOCH3
4ꢀBr
8g
8h
8i
3ꢀF
10
11
12
8j
CH3
CH3
CH3
H
8k
8l
4ꢀCOCH3
3ꢀCOCH3

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13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
8m
8n
8o
8p
8q
8r
CH3
4ꢀCH3
3ꢀCH3
4ꢀOCH3
2ꢀOCH3
4ꢀBr
40
45
40
40
40
40
45
40
40
45
50
40
40
40
40
40
50
50
87
80
9
CH3
CH3
CH3
70
68
76
76
76
83
79
73
87
80
74
75
78
85
77
CH3
CH3
3ꢀF
8s
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
OCH3
H
8t
4ꢀCOCH3
3ꢀCOCH3
4ꢀCH3
3ꢀCH3
4ꢀOCH3
2ꢀOCH3
4ꢀBr
8u
8v
8w
8x
8y
8z
8a'
8b'
8c'
8d'
3ꢀF
4ꢀF
4ꢀCl
2ꢀCl

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a
The first step involves the reaction of 4ꢀ(propꢀ2ꢀynꢀ1ꢀyloxy)benzaldehyde (3) (1.8 mmol), phenyl azide (5a-c)
2.2 mmol), CuSO .5H O (0.35 mmol) and Dꢀglucose (0.75 mmol) in THF/H O solvent under microwave
(
4
2
2
irradiation for the appropriate time and temperature at 100 W maximum power, followed by the addition of
b
c
aniline (7a-i) (2.2 mmol) and thioglycollic acid (6) (2.2 mmol), 15 min; isolated yields.
Conclusions
In summary, we have developed a convenient route for the synthesis of thaizolidinones
linked triazoles through a Cu(I)ꢀcatalyzed oneꢀpot sequential approach. The products could
be isolated in good yields. Work is ongoing to investigate the biological properties of these
novel heterocyclic compounds.
Experimental Section
General Information: All microwave assisted experiments were run in a closed vial
applying a dedicated CEMꢀDiscover monomode microwave apparatus operating at a
frequency of 2.45 GHz with continuous irradiation power from 0 to 300 W (CEM
Corporation, P.O. Box 200, Matthews, NC 28106). Analytical TLCs were performed on
Merck silica gel 60F254 plates. All liquid column chromatographic separations were
performed on column chromatography. IR spectra were recorded on a PerkinꢀElmer 2000 FTꢀ
1
13
IR spectrometer at Department of Chemistry, University of Delhi. The H and C NMR
spectra (in CDCl ) were recorded on a JEOL ECXꢀ400P NMR/Bruker Avance at 400
3
MHz/300 MHz and 100 MHz/75 MHz, respectively at USIC, University of Delhi/Katholiek
University Leuven, TMS was used as internal standard. The NMR spectra were processed by
TM
JEOL Delta NMR data processing software, the chemical shift values are on a δ scale and
coupling constants (J) are in ppm and Hz respectively. Abbreviations used are: s (singlet), d
(doublet), t (triplet), dd (double doublet) and m (multiplet). The highꢀresolution mass spectral

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data was obtained using a JEOL JMSꢀSXꢀ102A spectrometer at Institute for Chemistry and
Biochemistry, Free University Berlin, Germany. Melting points were recorded on a Buchi Mꢀ
560 melting point apparatus and are uncorrected. All the chemicals and reagents like phenol,
aniline, thioglycolic acid and propargyl bromide were purchased from commercial sources
and used as received unless otherwise indicated.
32
General procedure for the synthesis of 4-(prop-2-yn-1-yloxy) benzaldehyde or
propargyloxybenzaldehyde (3):
A mixture of 4ꢀhydroxy benzaldehyde (1 mmol) and propargyl bromide (1.2 mmol) in DMF
(
2 mL) as solvent was stirred with K CO at r. t. for 24 h. The progress of the reaction was
2 3
monitored on TLC [ethyl acetate/petroleum ether (1:4)]. After completion of the reaction, the
mixture was extracted with ethyl acetate (3 x 50 mL). The combined ethyl acetate layers were
dried over Na SO , filtered and concentrated under reduced pressure. The crude product was
2
4
directly used in the next step without any further purification.
33
General procedure for the synthesis of azidobenzene and its derivatives (5a-c)
o
A mixture of appropriate aniline 4 (a-c) (1 mmol) in HCl (17 %, 5 mL) was stirred at 0 C.
Sodium nitrite (1.5 equiv., dissolved in 5 mL of water) was added dropwise and stirring
o
continued at 0 C. After 15 min, sodium azide (1.5 equiv., dissolved in 5 mL of water) was
o
added dropwise at 0 C and the mixture was stirred for 3ꢀ4 h. The progress of the reaction
was monitored by TLC [ethyl acetate/petroleum ether (1:5)]. After completion of the
reaction, the reaction mixture was extracted with ethyl acetate (3 x 50 mL). The combined
ethyl acetate layers were dried over Na SO , filtered and concentrated under reduced
2
4
pressure. The crude product was directly used in the next step without any further
purification.

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Synthesis of 3-phenyl-2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)thiazolidin-
-one and its derivatives (8a-d')
A mixture of the alkyne (1 mmol), the appropriate azide (1.2 mmol), CuSO 5H O (0.2 equiv)
4
.
4
2
and DꢀGlucose were taken in THF/H O (2:1) in microwave transparent glass vial equipped
2
with a small magnetic stirring bar, and the vial was tightly sealed with a Teflon crimp cap.
o
The mixture was then irradiated for 15 min at 70 C and 100 W maximum power. The
reaction mixture was cooled to r. t. and aniline (1.2 mmol) and thioglycolic acid (1.2 mmol)
were added. The reaction mixture was irradiated again for appropriate time (40ꢀ50 min) at 70
o
C and 100 W maximum power. The progress of the reaction was monitored by TLC [ethyl
acetate/petroleum ether (1:2)]. After completion of the reaction, the mixture was extracted
with ethyl acetate (3 x 50 mL). The combined ethyl acetate layers were dried over Na SO ,
2
4
filtered and concentrated under reduced pressure. The crude product was purified by column
chromatography over silica gel to yield the desired products 8a-d'.
3-phenyl-2-[4-{(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy}phenyl]thiazolidin-4-one (8a)
o
ꢀ1
It was obtained as white solid having m. p. 169ꢀ171 C in 75% yield. IR (KBr) ν (cm ) =
max
1
2
931 (CꢀH, Ar), 1689 (C=O), 1226 (CꢀO), 765 (CꢀSꢀC); H NMR (300 MHz, CDCl ) δ 8.00
3
(s, 1H, Hꢀ5), 7.72 (dd, J = 1.5, 6.5 Hz, 2H, Ar), 7.53ꢀ7.45 ( m, 3H, Ar), 7.29ꢀ7.23 (m, 4H,
Ar), 7.176ꢀ7.12 (m, 3H, Ar), 6.92(dd, J = 2.1, 6.5 Hz, 2H, Ar), 6.07 (s, 1H, Hꢀ7"), 5.24 (s,

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1
3
2
H, ꢀOCH ), 3.98 (dd, J = 1.5, 16.1 Hz, 1H, Hꢀ9"), 3.87 (d, J = 16.0 Hz, 1H, Hꢀ9"); C
2
NMR (75 MHz, CDCl ) δ 170.918 (C=O), 158.51 (Cꢀ1"), 144.56, 137.45, 136.90, 131.89,
3
129.80, 129.09, 128.95, 128.64, 127.12, 125.89, 120.95, 120.61, 115.01, 65.31 (Cꢀ7"), 61.99
+
(
–OCH ), 33.58 (Cꢀ9"); HRMS calcd. for C H N O SH: 429.5141; found [M+H] :
2
24 20
4
2
429.5215.
3-(4-acetylphenyl)-2-[4-{(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy}phenyl] thiazolidin-4-
one (8b)
o
ꢀ
It was obtained as a white solid with a m. p. of 123ꢀ125 C in 82% yield. IR (KBr) ν (cm
max
1
1
)
= 2923 (ꢀCꢀH, Ar), 1679 (C=O), 1599 (C=O), 1267 (CꢀO), 758 (CꢀSꢀC); H NMR (300
MHz, CDCl ) δ 8.02 (s, 1H, Hꢀ5), 7.86 (d, J = 7.5 Hz, 2H, Ar), 7.72 ( d, J = 7.32 Hz, 2H,
3
Ar), 7.54ꢀ7.42 (m, 3H, Ar), 7.34ꢀ7.22 (m, 4H, Ar), 7.31 (d, J = 8.05 Hz, 2H, Ar), 7.25ꢀ7.21
(
m, 2H, Ar), 6.93 (d, J = 8.02 Hz, 2H, Ar), 6.19 (s, 1H, Hꢀ7"), 5.27 (s, 2H, ꢀOCH ), 3.96 (d, J
2
13
=
16.2 Hz, 1H, Hꢀ9"), 3.86 (d, J = 16.2 Hz, 1H, Hꢀ9"), 2.52 (s, 3H, ꢀCOCH ); C NMR (100
3
MHz, CDCl ) δ 197.00 (ꢀCOCH ), 171.03 (Cꢀ10"), 158.59 (Cꢀ1"), 144.39, 141.70, 136.81,
3
3
134.80, 131.18, 129.78, 129.11, 128.98, 128.34, 124.63, 121.02, 120.56, 115.15, 64.67 (Cꢀ

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7"), 61.90 (ꢀOCH ), 33.59 (Cꢀ9"), 26.49 (ꢀCOCH ); HRMS calcd. for C H N O SH:
2 3 26 22 4 3
+
4
71.5508; found [M+H] : 471.5514.
3-(3-acetylphenyl)-2--[4-{(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy}phenyl] thiazolidin-4-
one (8c)
ꢀ1
It was obtained as a brown semi solid in 76% yield. IR (KBr) νmax (cm ) = 2925 (CꢀH, Ar),
1
1
1
2
685 (C=O), 1598 (C=O), 1240 (CꢀO), 758 (CꢀSꢀC); H NMR (300 MHz, CDCl ) δ 8.02 (s,
3
H, Hꢀ5), 7.74ꢀ7.70 (m, 4H, Ar), 7.55ꢀ7.44 (m, 5H, Ar) 7.38ꢀ7.36 (m, 2H, Ar), 6.92 (dd, J =
.2, 6.5 Hz, 2H, Ar), 6.14 (s, 1H, Hꢀ7"), 5.22 (s, 2H, ꢀOCH ), 3.98 (dd, J = 1.7, 14.6 Hz, 1H,
2
1
3
Hꢀ9"), 3.88 (d, J = 15.6 Hz, 1H, Hꢀ9"), 2.50 (s, 3H, ꢀCOCH ); C NMR (100 MHz, CDCl )
3
3
δ 197.08 (ꢀCOCH ), 171.12 (Cꢀ10"), 158.59 (Cꢀ1"), 144.38, 137.84, 137.76, 136.89, 131.16,
3
1
7
4
30.47, 129.77, 129.32, 128.98, 128.73, 126.89, 125.23, 121.02, 120.56, 115.06, 65.06 (Cꢀ
"), 61.83 (ꢀOCH ), 33.54 (Cꢀ9"), 26.56 (ꢀCOCH ); HRMS calcd. for C H N O SH:
2
3
26 22
4
3
+
71.5508; found [M+H] : 471.5521.
-[4-{(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy}phenyl]-3-(p-tolyl)thiazolidin-4-one (8d)
2

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H C
3
13''
14''
1
11''
N
2''
O
''
1
5''
1
6''
5
10''
''
9''
4
''
6
''
S
8
3
'
7''
2
1
'
5
4
1
'
O
3''
4'
1''
N
2''
N
3
N
2
5
'
6'
8d
o
It was obtained as a yellowish solid with a m. p. of 166.0ꢀ168.0 C in 75% yield. IR (KBr)
ꢀ1
1
νmax (cm ) = 2924 (CꢀH, Ar), 1681 (C=O), 1239 (CꢀO), 757 (CꢀSꢀC); H NMR (400 MHz,
CDCl ) δ 8.01 (s, 1H, Hꢀ5), 7.70 (d, J = 8.05 Hz, 2H, Ar), 7.49 (d, J = 7.32 Hz, 2H, Ar) 7.45ꢀ
3
7
2
1
.41 (m, 1H, Ar), 7.24ꢀ7.21 (m, 2H, Ar), 7.04 (d, J = 7.32 Hz, 2H, Ar), 6.97 (d, J = 8.05 Hz,
H, Ar), 6.90 (d, J = 8.05 Hz, 2H, Ar), 6.00 (s, 1H, Hꢀ7"), 5.22 (s, 2H, ꢀOCH ), 3.95 (d, J =
2
13
6.1 Hz, 1H, Hꢀ9"), 3.85 (d, J = 16.1 Hz, 1H, Hꢀ9"), 2.22 (s, 3H, ꢀCH ); C NMR (100
3
MHz, CDCl ) δ 170.12 (Cꢀ10"), 158.42 (Cꢀ1"), 144.45, 137.07, 136.78, 134.62, 131.92,
3
1
29.70, 128.89, 128.64, 125.84, 120.99, 120.52, 114.89, 65.35 (Cꢀ7"), 61.88 (ꢀOCH ), 33.46
2
+
(
Cꢀ9"), 20.93 (ꢀCH ); HRMS calcd. for C H N O SH: 443.5407; found [M+H] : 443.5414.
3
25 22
4
2
2-[4-{(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy}phenyl]-3-(m-tolyl)thiazolidin-4-one (8e)
o
It was obtained as a yellowish solid with a m. p. of 181ꢀ183 C in 84% yield. IR (KBr) ν
max
ꢀ1
1
(
cm ) = 2924 (CꢀH, Ar), 1681 (C=O), 1238 (CꢀO), 759 (CꢀSꢀC); H NMR (400 MHz,

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CDCl ) δ 8.01 (s, 1H, Hꢀ5), 7.70 (d, J = 7.32 Hz, 2H, Ar), 7.52ꢀ7.49 (m, 2H, Ar), 7.45ꢀ7.41
3
(m, 1H, Ar), 7.24ꢀ7.21 (m, 2H, Ar), 7.13ꢀ7.09 (m, 1H, Ar), 6.95ꢀ6.85 (m, 5H, Ar), 6.02 (s,
1
H, Hꢀ7"), 5.23 (s, 2H, ꢀOCH ), 3.95 (d, J = 1.46, 16.11 Hz, 1H, Hꢀ9"), 3.84 (d, J = 16.11
2
1
3
Hz, 1H, Hꢀ9"), 2.23 (s, 3H, ꢀCH ); C NMR (100 MHz, CDCl ) δ 170.96 (Cꢀ10"), 158.43
3
3
(Cꢀ1"), 144.50, 139.00, 137.24, 136.82, 131.96, 129.75, 128.93, 128.81, 128.60, 128.05,
1
26.66, 122.93, 120.96, 120.56, 114.91, 65.36 (Cꢀ7"), 61.90 (ꢀOCH ), 33.52 (Cꢀ9"), 21.29 (ꢀ
2
+
CH ); HRMS calcd. for C H N O SH: 443.5407; found [M+H] : 443.5419.
3
25 22
4
2
3
-(4-methoxyphenyl)-2-[4-{(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy}phenyl] thiazolidin-
-one (8f)
4
ꢀ1
It was obtained as a brown semi solid in 82% yield. IR (KBr) νmax (cm ) = 2926 (CꢀH, Ar),
1
1
7
676 (C=O), 1215 (CꢀO), 758 (CꢀSꢀC); H NMR (300 MHz, CDCl ) δ 8.02 (s, 1H, Hꢀ5),
3
.72 (dd, J = 2.0, 7.6 Hz, 2H, Ar), 7.55ꢀ7.44 (m, 3H, Ar), 7.26ꢀ7.22 (m, 2H, Ar), 7.00ꢀ6.91
(
m, 4H, Ar), 6.79ꢀ6.76 (m, 2H, Ar), 5.96 (s, 1H, Hꢀ7"), 5.24 (s, 2H, ꢀOCH ), 3.97 (dd, J =
2
13
1
.7, 16.11 Hz, 1H, Hꢀ9"), 3.86 (d, J = 16.0 Hz, 1H, Hꢀ9") 3.71 (s, 3H, ꢀOCH ); C NMR
3
(
100 MHz, CDCl ) δ 171.14 (Cꢀ10"), 158.52 (Cꢀ1"), 144.51, 136.84, 131.91, 129.90, 129.77,
3
1
28.95, 128.83, 127.62, 120.97, 120.58, 114.91, 114.42, 65.67 (Cꢀ7"), 61.89 (ꢀOCH ), 55.28
2

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+
(
ꢀOCH ), 33.40 (Cꢀ9"); HRMS calcd. for C H N O SH: 459.5401; found [M+H] :
3
25 22
4
3
459.5417.
3
-(2-methoxyphenyl)-2-[4-{(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy}phenyl] thiazolidin-
-one (8g)
4
o
It was obtained as a white solid with a m. p. of 168.0ꢀ170.0 C in 76% yield. IR (KBr) ν
max
ꢀ1
1
(
cm ) = 2926 (CꢀH, Ar), 1686 (C=O), 1236 (CꢀO), 761 (CꢀSꢀC); H NMR (300 MHz,
CDCl ) δ 8.00 (s, 1H, Hꢀ5), 7.69 (d, J = 8.79 Hz, 2H, Ar), 7.52ꢀ7.41 (m, 3H, Ar), 7.26ꢀ7.24
3
(m, 2H, Ar), 6.87ꢀ6.82 (m, 4H, Ar), 6.77ꢀ6.74 (m, 1H, Ar), 6.05 (s, 1H, Hꢀ7"), 5.20 (s, 2H, ꢀ
1
3
OCH ), 3.90ꢀ3.80 (m, 2H, Hꢀ9"), 3.79 (s, 3H, ꢀOCH ); C NMR (100 MHz, CDCl ) δ
2
3
3
1
1
5
4
71.52 (Cꢀ10"), 158.45 (Cꢀ1"), 154.74, 144.50, 136.78, 131.32, 130.29, 129.74, 129.49,
29.39, 128.94, 125.24, 120.94, 120.71, 120.54, 114.53, 111.81, 64.35(Cꢀ7"), 61.79 (ꢀOCH2),
+
5.59 (ꢀOCH ), 33.24 (Cꢀ9"); HRMS calcd. for C H N O SH: 459.5401; found [M+H] :
3
25 22
4
3
59.5409.
-(4-bromophenyl)-2-[4-{(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy}phenyl] thiazolidin-4-
3
one (8h)

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o
It was obtained as a yellow solid with a m. p. of. 87.0ꢀ89.0 C in 62% yield. IR (KBr) ν
max
ꢀ1
1
(
cm ) = 2925 (CꢀH, Ar), 1685 (C=O), 1216 (CꢀO), 758 (CꢀSꢀC); H NMR (400 MHz,
CDCl ) δ 8.03 (s, 1H, Hꢀ5), 7.72 (d, J = 8.05 Hz, 2H, Ar), 7.53ꢀ7.43 (m, 3H, Ar), 7.38 (d, J =
3
8
8
3
1
1
5
.79 Hz, 2H, Ar), 7.22 (d, J = 8.05 Hz, 2H, Ar), 7.02 (d, J = 8.05 Hz, 2H, Ar), 6.93 (d, J =
.05 Hz, 2H, Ar), 6.04 (s, 1H, Hꢀ7"), 5.25 (s, 2H, ꢀOCH ), 3.95 (d, J = 16.11 Hz, 1H, Hꢀ9"),
2
1
3
.85 (d, J = 15.38 Hz, 1H, Hꢀ9"); C NMR (100 MHz, CDCl ) δ 170.90 (Cꢀ10"), 158.62 (Cꢀ
3
"), 144.49, 136.85, 136.45, 132.18, 131.32, 129.79, 128.99, 128.60, 127.23, 121.00, 120.59,
15.11, 65.05 (Cꢀ7"), 61.94 (ꢀOCH ), 33.48 (Cꢀ9"); HRMS calcd. for C H BrN O SH:
2
24 19
4
2
+
08.4102; found [M+H] : 508.4110.
-(3-fluorophenyl)-2-[4-{(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy}phenyl] thiazolidin-4-
3
one (8i)

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o
It was obtained as a white solid with a m. p. of 156.0ꢀ158.0 C in 71% yield. IR (KBr) ν
max
ꢀ1
1
(
cm ) = 2926 (CꢀH, Ar), 1675 (C=O), 1243 (CꢀO), 760 (CꢀSꢀC); H NMR (400 MHz,
CDCl ) δ 8.01 (s, 1H, Hꢀ5), 7.72 (dd, J = 1.09, 8.01 Hz, 2H, Ar), 7.54ꢀ7.51 (m, 2H, Ar),
3
7.47ꢀ7.43 (m, 1H, Ar), 7.25ꢀ7.19 (m, 3H, Ar), 6.98ꢀ6.82 (m, 5H, Ar), 6.07 (s, 1H, Hꢀ7"), 5.24
1
3
(
s, 2H, ꢀOCH ), 3.95 (dd, J = 1.6, 16.1 Hz, 1H, Hꢀ9"), 3.85 (d, J = 16.1 Hz, 1H, Hꢀ9"); C
2
NMR (100 MHz, CDCl ) δ 170.94 (Cꢀ10"), 158.60 (Cꢀ1"), 144.47, 131.44, 129.79, 128.96,
3
128.43, 120.93, 120.60, 115.12, 114.01, 113.84, 113.08, 112.85, 64.99 (Cꢀ7"), 61.97 (ꢀ
+
OCH ), 33.48 (Cꢀ9"); HRMS calcd. for C H FN O SH: 447.1291; found [M+H] :
2
24 19
4
2
447.1296.
3-phenyl-2-[4-{(1-(p-tolyl)-1H-1,2,3-triazol-4-yl}methoxy]phenyl)thiazolidin-4-one (8j)
o
It was obtained as a dark brown solid with a m. p. of 152.0ꢀ154.0 C in 85% yield. IR (KBr)
ꢀ1
1
νmax (cm ) = 2925 (CꢀH, Ar), 1701 (C=O), 1228 (CꢀO), 826 (CꢀSꢀC); H NMR (400 MHz,
CDCl ) δ 8.05 (s, 1H, Hꢀ5), 7.72 (d, J = 8.05 Hz, 2H, Ar), 7.54ꢀ7.43 (m, 4H, Ar), 7.26ꢀ7.23
3
(m, 1H, Ar), 7.06 (d, J = 7.32 Hz, 2H, Ar), 6.99 (d, J = 8.05 Hz, 2H, Ar), 6.92 (d, J = 8.05
Hz, 2H, Ar), 6.02 (s, 1H, Hꢀ7"), 5.24 (s, 2H, ꢀOCH ), 3.97 (d, J = 15.38 Hz, 1H, Hꢀ9"), 3.87
2
1
3
(
d, J = 16.11 Hz, 1H, Hꢀ9"), 2.24 (s, 2H, ꢀCH ); C NMR (100 MHz, CDCl ) δ 171.48 (Cꢀ
3
3
10"), 158.93 (Cꢀ1"), 144.97, 137.59, 137.29, 135.14, 132.44, 130.22, 129.41, 129.16, 126.35,

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1
21.50, 121.03, 115.40, 65.87 (Cꢀ7"), 62.40 (ꢀOCH ), 33.97 (Cꢀ9"), 21.45 (ꢀCH ); HRMS
2
3
+
calcd. for C H N O SH: 443.5407; found [M+H] : 443.5401.
2
5
22
4
2
3
4
-(4-acetylphenyl)-2-[4-{(1-(p-tolyl)-1H-1,2,3-triazol-4-yl)methoxy}phenyl] thiazolidin-
-one (8k)
o
It was obtained as a white solid with a m. p. of 137.0ꢀ139.0 C in 69 % yield. IR (KBr) ν
max
ꢀ1
1
(
cm ) = 2917 (CꢀH, Ar), 1683 (C=O), 1227 (CꢀO), 750 (CꢀSꢀC); H NMR (400 MHz,
CDCl ) δ 7.97 (s, 1H, Hꢀ5), 7.86 (d, J = 8.6 Hz, 2H, Ar), 7.58 (d, J = 8.6 Hz, 2H, Ar), 7.33ꢀ
3
7.29 (m, 4H, Ar), 7.23 (d, J = 8.6 Hz Hz, 1H, Ar), 7.21 (m, 1H, Ar), 6.93 (d, J = 8.00 Hz, 2H,
Ar), 6.18 (s, 1H, Hꢀ7), 5.22 (s, 2H, ꢀOCH ), 3.95 (d, J = 16.8 Hz, 1H, Hꢀ9"), 3.87 (d, J = 16.8
2
1
3
Hz, 1H, Hꢀ9"), 2.51 (s, 3H, ꢀCOCH ), 2.41 (s, 3H, ꢀCH ); C NMR (100 MHz, CDCl ) δ
3
3
3
1
1
97.05 (ꢀCOCH ), 170.97 (Cꢀ10"), 158.49 (Cꢀ1"), 144.31, 141.67, 139.21, 134.85, 134.57,
3
31.14, 130.26, 129.13, 128.32, 124.62, 120.98, 120.47, 115.17, 64.91 (Cꢀ7"), 61.69 (ꢀ
OCH ), 33.60 (Cꢀ9"), 26.53 (ꢀCOCH ), 21.08 (ꢀCH ); HRMS calcd. for C H N O SH:
2
3
3
27 24
4
3
+
4
85.5774; found [M+H] : 485.5770.
3
4
-(3-acetylphenyl)-2-[4-{(1-(p-tolyl)-1H-1,2,3-triazol-4-yl)methoxy}phenyl] thiazolidin-
-one (8l)

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ꢀ1
It was obtained as a dark brown semi solid in 74% yield. IR (KBr) νmax (cm ) = 2923 (CꢀH,
1
Ar), 1682 (C=O), 1240 (CꢀO), 757 (CꢀSꢀC); H NMR (400 MHz, CDCl ) δ 7.98 (s, 1H, Hꢀ
3
5
4
1
), 7.73ꢀ7.70 (m, 2H, Ar), 7.57 (d, J = 8.72 Hz, 2H, Ar), 7.36ꢀ7.35 (m, 2H, Ar), 7.30ꢀ7.26 (m,
H, Ar), 6.91 (d, J = 8.70 Hz, 2H, Ar), 6.13 (s, 1H, Hꢀ7"), 5.20 (s, 2H, ꢀOCH ), 3.97 (d, J =
2
6.03 Hz, 1H, Hꢀ9"), 3.88 (d, J = 16.03 Hz, 1H, Hꢀ9"), 2.49 (s, 3H, ꢀCOCH ), 2.40 (s, 3H, ꢀ
3
1
3
CH ); C NMR (100 MHz, CDCl ) δ 197.01 (ꢀCOCH ), 171.06 (Cꢀ10"), 158.55 (Cꢀ1"),
3
3
3
1
1
44.19, 138.89, 137.76, 134.48, 131.03, 130.44, 130.21, 129.28, 128.69, 126.84, 125.21,
20.98, 120.43, 115.03, 65.02 (Cꢀ7"), 61.84 (ꢀOCH ), 33.52 (Cꢀ9"), 26.53 (ꢀCOCH ), 21.04
2
3
+
(
ꢀCH ); HRMS calcd. for C H N O SH: 485.5774; found [M+H] : 485.5779.
3 27 24 4 3
3-(p-tolyl)-2-[4-{(1-(p-tolyl)-1H-1,2,3-triazol-4-yl)methoxy}phenyl]thiazolidin-4-one
(8m)
H C
3
13''
14''
1
11''
N
2''
O
''
1
5''
1
6''
5
10''
''
9''
4
''
6
''
S
8
3
'
7''
2
1'
'
5
4'
1
4
H C
3
O
3''
1''
N
2''
N
3
N
2
5
'
6'
8m

Page 21 of 38
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o
It was obtained as a white solid with a m. p. of 159.0ꢀ161.0 C in 87% yield. IR (KBr) ν
max
ꢀ1
1
(
cm ) = 2925 (CꢀH, Ar), 1690 (C=O), 1232 (CꢀO), 819 (CꢀSꢀC); H NMR (400 MHz,
CDCl ) δ 7.97 (s, 1H, Hꢀ5), 7.59 (d, J = 2.48, 6.4 Hz, 2H, Ar), 7.31 (d, J = 8.4 Hz, 2H, Ar),
3
7
6
9
.25ꢀ7.23 (m, 2H, Ar),7.06 (d, J = 8.4 Hz, 2H, Ar), 7.04ꢀ6.97 (m, 2H, Ar), 6.93 (dd, J = 2.4,
.8 Hz, 2H, Ar), 6.01 (s, 1H, Hꢀ7"), 5.22 (s, 2H, ꢀOCH ), 3.97 (dd, J = 1.6, 15.6 Hz, 1H, Hꢀ
2
13
"), 3.86 (d, J = 15.6 Hz, 1H, Hꢀ9"), 2.42 (s, 3H, ꢀCH ), 2.24 (s, 3H, ꢀCH ); C NMR (100
3
3
MHz, CDCl ) δ 171.02 (Cꢀ10"), 158.47 (Cꢀ1"), 144.30, 139.08, 137.12, 134.63, 134.53,
3
131.90, 130.22, 129.73, 128.66, 125.87, 120.94, 120.45, 114.90, 65.39 (Cꢀ7"), 61.87 (ꢀ
OCH ), 33.48 (Cꢀ9"), 21.05 (ꢀCH ), 20.96 (ꢀCH ); HRMS calcd. for C H N O SH:
2
3
3
26 24
4
2
+
4
57.5673; found [M+H] : 457.5679.
3-(m-tolyl)-2-[4-{(1-(p-tolyl)-1H-1,2,3-triazol-4-yl)methoxy}phenyl]thiazolidin-4-one (8n)
o
It was obtained as a white solid with a m. p. of 227.0ꢀ229.0 C in 80% yield. IR (KBr) ν
max
ꢀ1
(
cm ) = 2926 (CꢀH, Ar), 1676 (C=O), 1237 (CꢀO), 824 (CꢀSꢀC); NMR (300 MHz, CDCl ) δ
3
7
1
2
.97 (s, 1H, Hꢀ5), 7.58 (dd, J = 2.4, 8.4 Hz, 2H, Ar), 7.32ꢀ7.21 (m, 4H, Ar), 7.16ꢀ7.1028 (m,
H, Ar), 7.97ꢀ6.86 (m, 5H, Ar), 6.04 (s, 1H, Hꢀ7"), 5.22 (s, 2H, ꢀOCH ), 3.97 (dd, J = 2.4,
2
1.2 Hz, 2H, Hꢀ9"), 3.85 (d, J = 15.3 Hz, 1H, Hꢀ9"), 2.41 (s, 3H, ꢀCH ), 2.21 (s, 3H, ꢀCH );
3
3
1
3
C NMR (100 MHz, CDCl ) δ 171.50 (Cꢀ10"), 158.95 (Cꢀ1"), 144.78, 139.57, 137.60,
3
135.12, 135.01, 132.38, 130.70, 130.22, 129.15, 126.35, 121.42, 120.94, 115.38, 65.88 (Cꢀ

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7
"), 62.36 (ꢀOCH ), 33.96 (Cꢀ9"), 21.53 (ꢀCH ), 21.44 (ꢀCH ); HRMS calcd. for
2 3 3
+
C H N O SH: 457.5673; found [M+H] : 457.5670.
26
24
4
2
3-(4-methoxyphenyl)-2-[4-{(1-(p-tolyl)-1H-1,2,3-triazol-4-yl)methoxy}phenyl]
thiazolidin-5-one (8o)
o
It was obtained as a yellowish solid with a m. p. of 123.0ꢀ125.0 C in 69% yield. IR (KBr)
ꢀ1
1
νmax (cm ) = 2923 (CꢀH, Ar), 1678 (C=O), 1246 (CꢀO), 757 (CꢀSꢀC); H NMR (400 MHz,
CDCl ) δ 7.98 (s, 1H, Hꢀ5), 7.60 (d, J = 8.4 Hz, 2H, Ar), 7.32 (d, J = 8.0 Hz, 2H, Ar), 7.26ꢀ
3
7.23 (m, 2H, Ar), 7.00 (dd, J = 2.0, 6.8 Hz, 2H, Ar), 6.94 (d, J = 8.4 Hz, 2H, Ar), 6.79 (dd, J
=
2.7, 7.3 Hz, 2H, Ar), 5.96 (s, 1H, Hꢀ7"), 5.24 (s, 2H, ꢀOCH ), 3.98 (dd, J = 1.6, 15.6 Hz,
2
1
3
1
H, Hꢀ9"), 3.87 (d, J = 16.0 Hz, 1H, Hꢀ9"), 3.73 (s, 3H, ꢀOCH ), 2.43 (s, 3H, ꢀCH ); C
3 3
NMR (100 MHz, CDCl ) δ 171.04 (Cꢀ10"), 158.53 (Cꢀ1"), 144.30, 139.12, 134.50, 131.90,
3
130.26, 129.93, 128.82, 127.62, 120.98, 120.48, 114.90, 114.41, 65.62 (Cꢀ7"), 61.90 (ꢀ
OCH ), 55.28 (ꢀOCH ), 33.40 (Cꢀ9"), 21.07 (ꢀCH ); HRMS calcd. for C H N O SH:
2
3
3
26 24
4
3
+
4
73.5667; found [M+H] : 473.5660.
3-(2-methoxyphenyl)-2-[4-{(1-(p-tolyl)-1H-1,2,3-triazol-4-
yl)methoxy}phenyl]thiazolidin-4-one (8p)

Page 23 of 38
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o
It was obtained as a white solid with a m. p. of 237.0ꢀ239.0 C in 70% yield. IR (KBr) ν
max
ꢀ1
1
(
cm ) = 2922 (CꢀH, Ar), 1672 (C=O), 1271 (CꢀO), 757 (CꢀSꢀC); H NMR (300 MHz,
CDCl ) δ 7.95 (s, 1H, Hꢀ5), 7.59 (d, J = 8.8 Hz, 2H, Ar), 7.32ꢀ7.14 (m, 5H, Ar), 6.90ꢀ6.75ꢀ
3
7
.20 (m, 5H, Ar), 6.06 (s, 1H, Hꢀ7"), 5.21 (s, 2H, ꢀOCH ), 3.90 (s, 2H, Hꢀ9"), 3.82 (s, 3H, ꢀ
2
13
OCH ), 2.42 (s, 3H, ꢀCH ); C NMR (100 MHz, CDCl ) δ 171.10 (Cꢀ10"), 159.99 (Cꢀ12"),
3
3
3
1
1
58.45 (Cꢀ1"), 141.18, 137.18, 134.58, 131.92, 129.76, 128.69, 125.90, 122.25, 121.22,
20.03, 114.91, 114.78, 65.44 (Cꢀ7"), 61.82 (ꢀOCH ), 55.61 (ꢀOCH ), 33.50 (Cꢀ9"), 20.99 (ꢀ
2
3
+
CH ); HRMS calcd. for C H N O SH: 473.5667; found [M+H] : 473.5662.
3
26 24
4
3
3-(4-bromophenyl)-2-[4-{(1-(p-tolyl)-1H-1,2,3-triazol-4-yl)methoxy}phenyl] thiazolidin-
4-one (8q)

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DOI: 10.1039/C4RA12592D
o
It was obtained as a white solid with a m. p. of 180.0ꢀ182.0 C in 68% yield. IR (KBr) ν
max
ꢀ1
1
(
cm ) = 2926 (CꢀH, Ar), 1684 (C=O), 1231 (CꢀO), 823 (CꢀSꢀC); H NMR (400 MHz,
CDCl ) δ 7.98 (s, 1H, Hꢀ5), 7.59 (d, J = 8.4 Hz, 2H, Ar), 7.40ꢀ7.36 (m, 2H, Ar), 7.31 (d, J =
3
8.4 Hz, 2H, Ar), 7.24ꢀ7.20 (m, 2H, Ar), 7.03 (d, J = 8.8 Hz, 2H, Ar), 6.94 (d, J = 8.8 Hz, 2H,
Ar), 6.04 (s, 1H, Hꢀ7"), 5.23 (s, 2H, ꢀOCH ), 3.95 (dd, J = 1.2, 15.6 Hz, 1H, Hꢀ9"), 3.85 (d, J
2
1
3
=
15.6 Hz, 1H, Hꢀ9"), 2.42 (s, 3H, ꢀCH ); C NMR (100 MHz, CDCl ) δ 170.87 (Cꢀ10"),
3 3
1
1
58.64 (Cꢀ1"), 144.26, 139.10, 136.44, 134.55, 132.17, 131.26, 130.26, 128.57, 127.22,
20.97, 120.58, 120.46, 115.09, 64.98 (Cꢀ7"), 61.95 (ꢀOCH ), 33.47 (Cꢀ9"), 21.07 (ꢀCH );
2
3
+
HRMS calcd. for C H BrN O SH: 522.4368; found [M+H] : 522.4360.
2
5
21
4
2
3-(3-fluorophenyl)-2-[4-{(1-(p-tolyl)-1H-1,2,3-triazol-4-yl)methoxy}phenyl] thiazolidin-
4-one(8r)
o
ꢀ
It was obtained as a white solid with a m. p. of 276ꢀ278 C in 76% yield. IR (KBr) ν (cm
max
1
1
)
= 2928 (CꢀH, Ar), 1638 (C=O), 1255 (CꢀO), 825 (CꢀSꢀC); H NMR (400 MHz, CDCl ) δ
3
8
1
2
1
.05 (s, 1H, Hꢀ5), 7.41 (d, J = 8.05 Hz, 2H, Ar), 7.54 (t, J = 7.32 Hz, 2H, Ar), 7.49ꢀ7.45 (m,
H, Ar), 7.26 (d, J = 8.05 Hz, 2H, Ar), 7.08 (d, J = 7.32 Hz, 2H, Ar), 7.01 (d, J = 8.05 Hz,
H, Ar), 6.94 (d, J = 8.05 Hz, 1H, Ar), 6.04 (s, 1H, Hꢀ7"), 5.26 (s, 2H, ꢀOCH ), 3.98 (d, J =
2
13
6.11 Hz, 1H, Hꢀ9"), 3.88 (d, J = 16.11 Hz, 1H, Hꢀ9"), 2.26 (s, 3H, ꢀCH ); C NMR (100
3

Page 25 of 38
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DOI: 10.1039/C4RA12592D
MHz, CDCl ) δ 170.04 (Cꢀ10"), 157.66 (Cꢀ1"), 143.11, 138.07, 133.64, 130.45, 129.37,
3
127.69, 120.84, 120.19, 119.47, 114.14, 112.86, 112.66, 112.19, 111.95, 63.74 (Cꢀ7"), 60.75
(
ꢀOCH ), 32.56 (Cꢀ9"), 20.17 (ꢀCH ); HRMS calcd. for C H FN O SH: 461.5312; found
2
3
25 21
4
2
+
[
M+H] : 461.5318.
2
-[4-{(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methoxy}phenyl]-3-phenylthiazolidin-
-one (8s)
4
o
It was obtained as a yellowish solid with a m. p. of 170.0ꢀ172.0 C in 76 % yield. IR (KBr)
ꢀ1
1
νmax (cm ) = 2924 (CꢀH, Ar), 1683 (C=O), 1248 (CꢀO), 757 (CꢀSꢀC); H NMR (400 MHz,
CDCl ) δ 7.92 (s, 1H, Hꢀ5), 7.64ꢀ7.60 (m, 2H, Ar), 7.29ꢀ7.23 (m, 4H, Ar), 7.18ꢀ7.12 (m, 2H,
3
Ar),7.04ꢀ7.01 (m, 2H, Ar), 6.92 (d, J = 8.05 Hz, 2H, Ar), 6.07 (s, 1H, Hꢀ7"), 5.22 (s, 2H, ꢀ
1
3
OCH ), 4.00ꢀ3.85 (m, 5H, Hꢀ9" & ꢀOCH ); C NMR (100 MHz, CDCl ) δ 170.93 (Cꢀ10"),
2
3
3
1
1
59.88 (Cꢀ4'), 158.49 (Cꢀ1"), 144.23, 137.36, 131.75, 130.26, 129.04, 128.59, 127.09,
25.85, 122.20, 121.11, 114.93, 114.73, 65.28 (Cꢀ7"), 61.91 (ꢀOCH ), 55.58 (ꢀOCH ), 33.52
2
3
+
(
Cꢀ9"); HRMS calcd. for C H N O SH: 459.5401; found [M+H] : 459.5407.
25 22 4 3
3-(4-acetylphenyl)-2-[4-{(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methoxy}phenyl]
thiazolidin-4-one (8t)

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Page 26 of 38
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DOI: 10.1039/C4RA12592D
o
It was obtained as a yellow solid with a m. p. of 131.0ꢀ133.0 C in 76% yield. IR (KBr) ν
max
ꢀ1
1
(
cm ) = 2925 (CꢀH, Ar), 1685 (C=O), 1230 (CꢀO), 837 (CꢀSꢀC); H NMR (300 MHz,
CDCl ) δ 7.93 (s, 1H, Hꢀ5), 7.86 (dd, J = 2.8, 8.8 Hz, 2H, Ar), 7.60 (dd, J = 2.8, 8.8 Hz, 2H,
3
Ar), 7.32 (dd, J = 2.8, 8.8 Hz, 2H, Ar), 7.26ꢀ7.22 (m, 2H, Ar), 7.03ꢀ6.99 (m, 2H, Ar), 6.94ꢀ
6
.91 (m, 2H, Ar), 6.18 (s, 1H, Hꢀ7"), 5.21 (s, 2H, ꢀOCH ), 3.99ꢀ3,83 (m, 5H, Hꢀ9" & ꢀ
2
13
OCH ), 2.52 (s, 3H, ꢀCOCH ); C NMR (100 MHz, CDCl ) δ 197.37 (ꢀCOCH ), 176.27 (Cꢀ
3
3
3
3
1
0"), 171.16, 159.61 (Cꢀ4'), 158.57 (Cꢀ1"), 141.78, 134.72, 131.13, 129.14, 128.35, 124.68,
22.24, 115.15, 114.80, 64.70 (Cꢀ7"), 61.80 (ꢀOCH ), 55.61 (ꢀOCH ), 33.60 (Cꢀ9"), 26.50 (ꢀ
1
2
3
+
COCH ); HRMS calcd. for C H N O SH: 501.5768; found [M+H] : 501.5760.
3
27 24
4
4
3-(3-acetylphenyl)-2-[4-{(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methoxy}phenyl]
thiazolidin-4-one (8u)

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DOI: 10.1039/C4RA12592D
ꢀ1
It was obtained as a brown semi solid in 83% yield. IR (KBr) νmax (cm ) = 2922 (CꢀH, Ar),
1
1
7
7
3
683 (C=O), 1247 (CꢀO), 759 (CꢀSꢀC); H NMR (300 MHz, CDCl ) δ 7.93 (s, 1H, Hꢀ5),
3
.74ꢀ7.71 (m, 2H, Ar), 7.62ꢀ7.58 (m, 2H, Ar), 7.38ꢀ7.36 (m, 1H, Ar), 7.27ꢀ7.24 (m, 2H, Ar),
.02ꢀ6.99 (m, 2H, Ar), 6.93ꢀ6.90 (m, 2H, Ar), 6.11 (s, 1H, Hꢀ7"), 5.20 (s, 2H, ꢀOCH ), 4.01ꢀ
2
13
.86 (m, 5H, Hꢀ9" & ꢀOCH ), 2.50 (s, 3H, ꢀCOCH ); C NMR (100 MHz, CDCl ) δ 197.12
3
3
3
(
ꢀCOCH ), 171.17 (Cꢀ10"), 159.94 (Cꢀ4'), 159.60 (Cꢀ1"), 144.09, 131.08, 130.48, 130.15,
3
129.31, 128.72, 126.91, 125.25, 122.21, 121.22, 115.04, 114.75, 65.08 (Cꢀ7"), 61,79 (ꢀ
OCH ), 55.59 (ꢀOCH ), 33.54 (Cꢀ9"), 26.55 (ꢀCOCH ); HRMS calcd. for C H N O SH:
2
3
3
27 24
4
4
+
5
01.5768; found [M+H] : 501.5762.
2-[4-{(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methoxy}phenyl]-3-(p-tolyl)
thiazolidin-4-one (8v)
H C
3
13''
14''
1
11''
N
2''
O
''
1
5''
1
6''
5
10''
''
9''
4
''
6
''
S
8
3
'
'
7''
2
1'
'
5
4
'
1
4
H CO
3
O
3''
1
''
N
2
''
N
3
N
2
5
6'
8
v

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Page 28 of 38
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DOI: 10.1039/C4RA12592D
o
ꢀ
It was obtained as a white solid with a m. p. of 100ꢀ102 C in 79% yield. IR (KBr) ν (cm
max
1
1
)
= 2923 (CꢀH, Ar), 1683 (C=O), 1238 (CꢀO), 758 (CꢀSꢀC); H NMR (300 MHz, CDCl ) δ
3
7
.93 (s, 1H, Hꢀ5), 7.61 (dd, J = 2.8, 8.8 Hz, 2H, Ar), 7.26ꢀ7.22 (m, 2H, Ar), 7.07ꢀ6.97 (m,
H, Ar), 6.92 (dd, J = 2.8, 8.8 Hz, 2H, Ar), 6.02 (s, 1H, Hꢀ7"), 5.21 (s, 2H,
6
13
ꢀ
OCH ), 3.99ꢀ3.83 (m, 5H, Hꢀ9" & ꢀOCH ), 2.24 (s, 3H, ꢀCH ); C NMR (100 MHz,
2 3 3
CDCl ) δ 171.10 (Cꢀ10"), 159.98 (Cꢀ4') , 158.45 (Cꢀ1"), 144.18, 137.18, 134.45, 131.92,
3
1
29.76, 128.69, 125.90, 122.25, 121.22, 114.91, 114.78, 65.44 (Cꢀ7"), 61.82 (ꢀOCH ), 55.61
2
(
ꢀOCH ), 33.50 (Cꢀ9"), 20.99 (ꢀCH ); HRMS calcd. for C H N O SH: 473.5667; found
3
3
26 24
4
3
+
[
M+H] : 473.5662.
2-[4-{(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methoxy}phenyl]-3-(m-tolyl)
thiazolidin-4-one (8w)
o
It was obtained as a white solid with a m. p. of 158.0ꢀ160.0 C in 73 % yield. IR (KBr) ν
max
ꢀ1
1
(
cm ) = 2925 (CꢀH, Ar), 1677 (C=O), 1241 (CꢀO), 833 (CꢀSꢀC); H NMR (300 MHz,
CDCl ) δ 7.93 (s, 1H, Hꢀ5), 7.60 (dd, J = 3.2, 8.8 Hz, 2H, Ar), 7.26ꢀ7.22 (m, 2H, Ar), 7.16ꢀ
3
7
.10 (m, 1H, Ar), 7.02ꢀ6.86 (m, 7H, Ar), 6.04 (s, 1H, Hꢀ7"), 5.21 (s, 2H, ꢀOCH ), 3.99ꢀ3.82
2
1
3
(
m, 5H, Hꢀ9" & ꢀOCH ), 2.25 (s, 3H, ꢀCH ); C NMR (100 MHz, CDCl ) δ 173.56 (Cꢀ
3 3 3
1
1
0"), 171.09, 159.92 (Cꢀ4'), 158.40 (Cꢀ1"), 144.15, 138.98, 137.13, 131.83, 130.13, 128.78,
28.59, 128.07, 126.65, 122.93, 122.18, 121.20, 114.88, 114.72, 65.39 (Cꢀ7"), 61.79 (ꢀ

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OCH ), 55.56 (ꢀOCH ), 33.49 (Cꢀ9"), 21.25 (ꢀCH ); HRMS calcd. for C H N O SH:
2
3
3
26 24
4
3
+
4
73.5667; found [M+H] : 473.5665.
3-(4-methoxyphenyl)-2-[4-{(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methoxy}phenyl]
thiazolidin-4-one (8x)
o
It was obtained as a white solid with a m. p. of 164.0ꢀ166.0 C in 87% yield. IR (KBr) ν
max
ꢀ1
1
(
cm ) = 2923 (CꢀH, Ar), 1681 (C=O), 1248 (CꢀO), 759 (CꢀSꢀC); H NMR (300 MHz,
CDCl ) δ 7.93 (s, 1H, Hꢀ5), 7.61 (d, J = 8.8 Hz, 2H, Ar), 7.24 (d, J = 8.8 Hz, 2H, Ar), 7.02ꢀ
3
6
7
.96 (m, 4H, Ar), 6.92 (d, J = 8.4 Hz, 2H, Ar), 6.77 (d, J = 8.8 Hz, 2H, Ar), 5.95 (s, 1H, Hꢀ
1
3
"), 5.22 (s, 2H, ꢀOCH ), 3.98ꢀ3.84 (m, 5H, Hꢀ9" & ꢀOCH ), 3.71 (s, 3H, ꢀOCH ), ; C
2
3
3
NMR (100 MHz, CDCl ) δ 171.00 (Cꢀ10"), 159.98, 158.41 (Cꢀ1"), 144.17, 131.95, 130.17,
3
129.94, 128.81, 127.60, 122.25, 121.28, 114.91, 114.78, 114.40, 65.58 (Cꢀ7"), 61.89 (ꢀ
OCH ), 55.60 (ꢀOCH ), 55.28 (ꢀOCH ), 33.39 (Cꢀ9"); HRMS calcd. for C H N O SH:
2
3
3
26 24
4
4
+
4
89.5661; found [M+H] : 489.5658.
3-(2-methoxyphenyl)-2-[4-{(1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methoxy}phenyl]
thiazolidin-4-one (8y)