Synthesis of 1,4-disubstituted 1,2,3-triazoles from aromatic α-bromoketones, sodium azide and terminal acetylenes via Cu/Cu(OTf) 2-catalyzed click reaction under microwave irradiation

Article abstract of DOI:10.5560/ZNB.2013-3043

Reaction of aromatic α-bromoketones, sodium azide and aromatic or aliphatic terminal acetylenes in the presence of Cu/Cu(OTf)₂ following the classical method (aqueous acetonitrile at room temperature) and under microwave irradiation (H₂

Full text of DOI:10.5560/ZNB.2013-3043

Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Aromatic
α-Bromoketones, Sodium Azide and Terminal Acetylenes via
Cu/Cu(OTf)2-catalyzed Click Reaction under Microwave Irradiation
Azadeh Fazelia, Hossein A. Oskooiea, Yahya S. Beheshtihaa, Majid M. Heravia, Firouz
Matloubi Moghaddamb, and Behzad Koushki Foroushanib
a
Department of Chemistry, School of Science, Alzahra University, P. O. Box 1993893973,
Vanak, Tehran, I. R. Iran
Department of Chemistry, Sharif University of Technology, Tehran, I. R. Iran
b
Reprint requests to Prof. Dr. Majid M. Heravi. Fax: +98-2188047861.
E-mail: mmh1331@yahoo.com
Z. Naturforsch. 2013, 68b, 391 – 396 / DOI: 10.5560/ZNB.2013-3043
Received February 11, 2013
Reaction of aromatic α-bromoketones, sodium azide and aromatic or aliphatic terminal acetylenes
in the presence of Cu/Cu(OTf)2 following the classical method (aqueous acetonitrile at room temper-
ature) and under microwave irradiation (H2O at 85 ◦C) leads to 1,4-disubstituted 1,2,3-triazoles as
the final products after simple filtration.
Key words: Click Reaction, Copper/Copper Triflate, Cycloaddition, α-Bromoketones,
1,4-Disubstituted 1,2,3-Triazoles, Three-Component Reaction, Microwave Irradiation
Introduction
Some of 1,4-disubstituted 1,2,3-triazoles have been
synthesized using the click chemistry between α-
Multi-component reactions (MCRs) are one of azidoketones and terminal acetylenes, and the products
the most important reactions in combinatorial chem- have shown modest Src kinase inhibitory activity [10].
istry [1]. In these reactions, compounds can be synthe- They are also important compounds for their cytotox-
sized from three or more compounds reacting in a few icity in A549 (lung cancer) [11], HT-29 (colon can-
steps and usually in a one-pot operation.
cer) [11] and He La (cervial cancer) [11]. In this pa-
1,2,3-Triazoles have a wide range of biologically per we wish to report a simple method for the synthe-
relevant properties such as anti-bacterial [2], anti- sis of these compounds using click reaction conditions
allergic [3] and anti-HIV [4] activity, and because of (Fig. 1).
these properties they are targets for drug discovery [5].
α-Azidoketones cannot be easily prepared by the re-
In 1963, Huisgen and his co-workers described a sys- action of sodium azide and α-bromoketones, because
tematic study on 1,3-dipolar cycloaddition between isolation and purification of some α-azidoketones is
azides and terminal alkynes [6]. This uncatalyzed cy- difficult [12]. Therefore, in situ generation of α-
cloaddition reaction was improved in 2002 by Mel- azidoketones from the reaction of α-bromoketones
dal [7] and Sharpless [8] via the use of copper(I) with sodium azide is very important. The cycload-
which can improve the rates and regioselectivity of the dition reaction between α-azidoketones and termi-
azide-alkyne cycloaddition reaction. Thus the Huis- nal acetylenes has been reported using various meth-
gen 1,3-dipolar cycloaddition to triazoles can be per- ods, including (1) CuSO4 · 5H2O/sodium ascorbate,
formed under copper catalysis in a click reaction and PEG-H2O [10]; (2) CuI, H2O or H2O-acetone [11];
is then known as copper-catalyzed azide-alkyne cy- (3) CuSO4/sodium ascorbate, PEG-H2O [12]; (4)
cloaddition (CuAAC) [9]. The CuAAC produces only CuI, PEG-H2O [13]; (5) CuSO4/sodium ascorbate,
1,4-disubstituted triazoles with excellent yields and t-BuOH-H2O [14]; and (6) P4VPy-CuI, H2O [15]
purities.
systems.
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A. Fazeli et al. · Synthesis of 1,4-Disubstituted 1,2,3-Triazoles
R
O
O
Cu/Cu(OTf)2
N
Br
+
NaN3 +
R
N
N
Ar
Ar
Method A and Method B
1
2
3
4
Method A (classical method): H2O-MeCN (1:1), r. t.
Method B (microwave irradiation): H2O, 85 o
C
Scheme 1. Synthesis of 1,4-disubstituted 1,2,3-triazoles.
R2
Table 1. Cu(I)-catalyzed 1,3-dipolar cycloaddition of 2-
bromo acetophenone with sodium azide and phenyl acety-
lene under classical conditionsa.
R1 = alkyl, aryl, cycloalkyl
O
N
R2 = alkyl, aryl, cycloalkyl
N
N
R1
Fig. 1. Structure of 1,4-disubstituted 1,2,3-triazoles.
O
O
N
catalyst
N
Br
+
NaN3 +
Ph
N
solvent
r. t.
In continuation of our studies of multi-component
reactions [16 – 21] and running organic reactions un-
der microwave irradiation [22 – 24], herein we wish
to report a facile synthesis of 1,4-disubstituted 1,2,3-
triazoles involving the three-component, one-pot con-
densation of α-bromoketones, sodium azide, and ter-
minal alkynes using the Cu/Cu(OTf)2 as a catalyst.
We investigated these procedures both by the classical
method and by microwave irradiation (Scheme 1).
2
3a
4a
1a
Entry
Catalystb
Solvent
Time
(h)
Yield
(%)c
1
2
3
4
5
6
7
8
Cu/Cu(OTf)2
Cu/Cu(OTf)2
Cu/Cu(OTf)2
Cu/Cu(OTf)2
Cu/Cu(OTf)2
Cu/Cu(OTf)2
Cu/Cu(OAc)2
Cu/Cu(OAc)2
Cu/CuSO4
DMSO-H2O
acetone-H2O
t-BuOH-H2O
MeCN-H2O
EtOH-H2O
MeOH-H2O
t-BuOH-H2O
MeCN-H2O
MeCN-H2O
MeCN-H2O
H2O
2.83
6.5
2.83
2.66
4
5.5
2.66
2.5
2.83
24
60
52
40
91
70
60
72
82
77
78
45
Results and Discussion
9
10
11
Cu(OTf)2
Cu/Cu(OTf)2
13
To optimize the cycloaddition reaction in the clas-
sical method, the reaction of 2-bromoacetophenone
with sodium azide and phenyl acetylene as an aro-
matic terminal alkyne was used as a model reaction.
In initial attempts, we examined the effect of various
Cu(I) catalysts such as Cu/Cu(OAc)2, Cu/CuSO4 and
a
All reactions were performed on a 0.5 mmol scale in 1.5 mL of
solvent at room temperature; 5 mol-% of Cu/Cu(II); yields are
given for isolated products.
b
c
Various aromatic α-bromoketones were examined
Cu/Cu(OTf)2 in various solvents such as H2O, MeOH- with the classical method to obtain 1,4-disubstituted
H2O, EtOH-H2O, DMSO-H2O, t-BuOH-H2O, MeCN- 1,2,3-triazoles. In this reaction, we investigated the ef-
H2O, and acetone-H2O at room temperature (Table 1, fects of phenylacetylene and other terminal acetylenes
entries 1 – 11).
with hydroxyl as a functional group in the reaction
In this reaction, the Cu(I) catalyst was prepared in of α-bromoketones and NaN3. The results with var-
situ by the comproportionation of Cu(0) and Cu(II), ious terminal acetylenes have demonstrated the hy-
and Cu/Cu(OTf)2 in aqueous acetonitrile was chosen droxyl group tolerance of this protocol (Table 2, entries
as an effective catalyst (Table 1, entry 4). The advan- 4 – 10).
tage of this catalyst is the availability of Cu(0) and
The use of microwave irradiation in this reaction
Cu(OTf)2 powder and the power of this mixture to instead of the conventional method was also investi-
produce 1,4-disubstituted 1,2,3-triazoles in high yields gated. The model reaction was examined in various
and short reaction times. The use of Cu(OTf)2 in the solvents and at different temperatures with controlled
absence of Cu powder gives the product in 24 h with microwave powers (200 – 700 W). The best result was
78% yield (Table 1, entry 10).
obtained in H2O as a solvent at 85 ◦C and 700 W. As
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A. Fazeli et al. · Synthesis of 1,4-Disubstituted 1,2,3-Triazoles
393
Table 2. Synthesis of 1,4-disub-
R
stituted 1,2,3-triazoles 4.
O
O
N
Cu/Cu(OTf)2
N
Br
+
NaN3 +
R
N
Ar
Ar
Method A and Method B
3a c
−
4a j
−
2
1a−e
Method A (classical method): H2O-MeCN (1:1), r. t.
Method B (microwave irradiation): H2O, 85 oC
Entry Ar (1a–e)
R (3a–c)
Product
Method Aa
Method Bb
(4a–j)
Time Yield Time Yield
(h)
(%)c (min) (%)c
1
2
3
4
5
6
7
8
9
Ph (1a)
Ph (3a)
Ph (3a)
Ph (3a)
CH2OH (3b)
C(CH3)2OH (3c)
CH2OH (3b)
C(CH3)2OH (3c)
CH2OH (3b)
C(CH3)2OH (3c)
CH2OH (3b)
4a
4b
4c
4d
4e
4f
4g
4h
4i
2.66
1.83
1.33
1.16
1.5
1.25
1.5
2
91
92
88
84
80
89
82
80
78
72
10
10
8
8
11
9
12
9
14
10
92
95
90
90
85
92
87
90
85
85
4-Me-C6H4 (1b)
4-Cl-C6H4 (1c)
Ph (1a)
4-Cl-C6H4 (1c)
4-Me-C6H4 (1b)
4-Me-C6H4 (1b)
4-Br-C6H4 (1d)
4-Br-C6H4 (1d)
4-Ph-C6H4 (1e)
2.16
2
10
4j
a
b
Under classical heating in aqueous acetonitrile at room temperature; under microwave
irradiation in water at 85 ◦C; c yields of pure products.
can be seen from Table 2, the yields of the products Cu/Cu(OTf)2 under the conventional method (aque-
and the reaction times under microwave irradiation are ous acetonitrile at room temperature) or under mi-
more acceptable than those for conventional methods. crowave irradiation (H2O at 85 ◦C) gave the corre-
Another advantage of this reaction under microwave ir- sponding 1,4-disubstituted 1,2,3-triazoles. In this reac-
radiation is the use of H2O as a “green solvent” instead tion the products could be separated by a simple filtra-
of aqueous acetonitrile in the classical method. Using tion. High yields, short reaction times, regioselective
H2O as a solvent in 13 h under the classical method synthesis and mild reaction conditions in the classi-
produced triazole 4a only in 45% yield (Table 1, entry cal method make this method very simple and useful
11).
for the prepration of 1,4-disubstituted 1,2,3-triazoles.
The progress of the reaction was monitored by TLC, However, this reaction was more facile and much
1
IR and H NMR. Disappearance of the azide absorp- faster, when it was performed under microwave irradi-
tion of the α-azidoketone (2100 cm−1) and creation ation. Because of homogeneous heating throughout the
of the triazole (1223 cm−1) and carbonyl (1701 cm−1
)
reaction media by microwave irradiation, the reactions
absorptions in the IR spectra indicated the formation were completed in shorter reaction time (8 – 14 min)
1
of 1,4-disubstituted 1,2,3-triazoles, and the H NMR and in higher yields (85 – 95%). Because H2O can
spectrum displayed a singlet at δ = 8.54 ppm for tria- be used as a solvent under microwave irradiation, we
zole H-5.
can claim that this one-pot, three-component protocol
has all qualities and superiorities expected from click
chemistry, which was first fully described by Sharpless
et al. in 2001 [25]. In comparison with other methods
Conclusion
In summary, we have developed mild reaction con- which needed long reaction times (8 – 12 h) [11, 12]
ditions for the regioselective synthesis of new deriva- and gave moderate yields (61 – 86%) [11, 13], this
tives of 1,4-disubstituted 1,2,3-triazoles. Reaction of method is completed in about one to three hours giving
aromatic α-bromoketones, sodium azide and aromatic good yields of products (72 – 92%) under the conven-
or aliphatic terminal acetylenes in the presence of tional method and in 8 – 14 minutes giving excellent
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A. Fazeli et al. · Synthesis of 1,4-Disubstituted 1,2,3-Triazoles
yields of products (85 – 95%) under microvawe irra- 128.76, 126.06, 123.95, 56.89 ppm. – IR (KBr): ν = 1701,
1223 cm−1
.
diation. The pure products are obtained by simple fil-
tration.
2-(4-Phenyl-[1,2,3]triazol-1-yl)-1-p-tolyl-ethanone (4b)
[11, 13, 26]
Experimental Section
M. p. 157 – 158 ◦C. – 1H NMR (500 MHz, DMSO): δ =
8.52 (s, 1H, CH), 8.00 – 7.99 (m, 2H, Ar), 7.88 – 7.87 (m,
2H, Ar), 7.47 – 7.33 (m, 5H, Ar), 6.21 (s, 2H, CH2), 2.41 (s,
3H, CH3) ppm. – 13C NMR (125 MHz, DMSO): δ = 192.48,
147.18, 145.76, 132.51, 131.64, 130.40, 129.80, 129.18,
128.72, 126.02, 123.95, 56.73, 22.15 ppm. – IR (KBr): ν =
Melting points were measured using a capillary tube
method with a Barnstead Electrothermal 9200 apparatus.
FTIR spectra were recorded using KBr discs on an FTIR
Bruker Tensor 27 instrument. 1H and 13C NMR spectra were
recorded on a Bruker AQS-Avance spectrometer at 500 and
125 MHz, respectively, using TMS as an internal standard.
Mass spectra were documented on an Agilent Technology
(HP) spectrometer operating at an ionization potential of
70 eV, and all reactions were carried out in an Ethos MR mi-
crowave reactor.
1695, 1232 cm−1
.
1-(4-Chlorophenyl)-2-(4-phenyl-[1,2,3]triazol-
1-yl)ethanone (4c) [11 – 13, 26]
M. p. 108 – 111 ◦C. – 1H NMR (500 MHz, DMSO): δ =
8.52 (s, 1H, CH), 8.12 – 7.87 (m, 4H, Ar), 7.71 – 7.34 (m, 5H,
Ar), 6.27 (s, 2H, CH2) ppm. – 13C NMR (125 MHz, DMSO):
δ = 192.25, 147.19, 140.08, 133.68, 131.57, 131.03, 130.02,
129.84, 128.77, 126.02, 123.89, 56.87 ppm. – IR (KBr): ν =
General procedure for the synthesis of 1,4-disubstituted
1,2,3-triazoles under the classical method (Method A)
To a stirred mixture of the α-bromoketone (1 mmol) and
sodium azide (1.5 mmol) in aqueous acetonitrile (5 mL), Cu
(10 mol-%), Cu(OTf)2 (10 mol-%) and terminal acetylene
(1.2 mmol) were added at room temperature, and the mix-
ture was stirred for the reaction time indicated in Table 2 (the
progress of reaction was monitored by TLC). After the com-
pletion of the reaction, the reaction mixture was diluted with
water and filtered to collect the product. The product was
washed with cold water and 0.2 M HCl (10 mL). For further
purification, the products should be washed with 10 mL of
ether (Table 2, condition A).
1710, 1230 cm−1
.
2-(4-Hydroxymethyl-[1,2,3]triazol-1-yl)-1-phenyl-ethanone
(4d) [11, 26]
1
M. p. 122 ◦C. – H NMR (500 MHz, DMSO): δ = 8.14
(s, 1H, CH), 8.06 – 8.05 (m, 2H, Ar), 7.75 – 7.72 (m, 1H, Ar),
7.62 – 7.59 (m, 2H, Ar), 6.23 (s, 2H, CH2), 5.39 (s, 1H, OH),
4.66 (s, 2H, CH2) ppm. – 13C NMR (125 MHz, DMSO): δ =
192.58, 135.16, 134.88, 129.86, 129.04, 57.31, 55.89 ppm. –
General procedure for the synthesis of 1,4-disubstituted
1,2,3-triazoles under microwave irradiation (Method B)
IR (KBr): ν = 3389, 1699, 1229 cm−1
.
1-(4-Chlorophenyl)-2-[4-(1-hydroxy-1-methylethyl)-
[1,2,3]triazol-1-yl]ethanone (4e) [27]
α-Bromoketone (1 mmol), sodium azide (1.5 mmol), ter-
minal acetylene (1.25 mmol), Cu (10 mol-%) and Cu(OTf)2
(10 mol-%) were added to water (7 mL) in a reaction ves-
sel of Ethos MR, and the vessel was capped. The reaction
mixture was irradiated for 8 – 14 min at 85 ◦C (the progress
of the reaction was monitored by TLC). After the comple-
tion of the reaction, the reaction mixture was cooled to room
temperature, diluted with water and filtered to collect the
product. The product was washed with cold water and 0.2 M
HCl (10 mL). For further purification, the products should be
washed with 10 mL of ether (Table 2, condition B).
M. p. 149 – 152 ◦C. – 1H NMR (500 MHz, DMSO): δ =
8.04 (m, 2H, Ar), 7.81 (s, 1H, CH), 7.66 – 7.65 (m, 2H, Ar),
6.12 (s, 2H, CH2), 5.44 (brs, 1H, OH), 1.51 (s, 6H, 2CH3)
ppm. – 13C NMR (125 MHz, DMSO): δ = 192.52, 139.93,
133.80, 130.92, 129.94, 56.8, 31.86 ppm. – IR (KBr): ν =
3350, 1702, 1231 cm−1. – MS (EI, 70 eV): m/z (%) = 279.4
(5) [M]+, 139 (100), 111 (91), 43 (85).
2-(4-Hydroxymethyl-[1,2,3]triazol-1-yl)-1-p-tolyl-ethanone
(4f)
1-Phenyl-2-(4-phenyl-[1,2,3]triazol-1-yl)ethanone (4a)
[11 – 13, 26]
M. p. 184 – 185 ◦C. – 1H NMR (500 MHz, DMSO): δ =
M. p. 169 – 171 ◦C. – 1H NMR (500 MHz, DMSO): δ = 8.04 (s, 1H, CH), 7.96 – 7.95 (m, 2H, Ar), 7.41 – 7.40 (m, 2H,
8.54 (s, 1H, CH), 8.12 – 7.34 (m, 10H, Ar), 6.28 (s, 2H, Ar), 6.13 (s, 2H, CH2), 5.27 (s, 1H, OH), 4.58 (s, 2H, CH2),
CH2) ppm. – 13C NMR (125 MHz, DMSO): δ = 193.05, 2.41 (s, 3H, CH3) ppm. – 13C NMR (125 MHz, DMSO):
147.20, 135.16, 135.00, 131.60, 129.88, 129.83, 129.100, δ = 192.40, 145.66, 132.56, 130.37, 129.13, 56.70, 55.98,
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A. Fazeli et al. · Synthesis of 1,4-Disubstituted 1,2,3-Triazoles
395
22.13 ppm. – IR (KBr): ν = 3420, 1696, 1235 cm−1. – MS 1-(4-Bromophenyl)-2-[4-(1-hydroxy-1-methylethyl)-
(EI, 70 eV): m/z (%) = 231.3 (3) [M]+, 202 (31), 169 (37), [1,2,3]triazol-1-yl]ethanone (4i)
119 (100), 91 (96), 65 (39). – C12H13N3O2: calcd. C 62.33,
M. p. 173 – 175 ◦C. – 1H NMR (500 MHz, DMSO):
δ = 7.99 – 7.97 (m, 2H, Ar), 7.84 (s, 1H, CH), 7.82 – 7.81
(m, 2H, Ar), 6.10 (s, 2H, CH2), 5.2 (s, 1H, OH), 1.48
(s, 6H, 2CH3) ppm. – 13C NMR (125 MHz, DMSO): δ =
192.52, 141.78, 134.13, 132.90, 131.00, 130.99, 129.15,
56.53, 50.84, 31.65 ppm. – IR (KBr): ν = 3301, 1702,
1228 cm−1. – MS (EI, 70 eV): m/z (%) = 324.2 (5) [M]+,
310 (66), 308 (66), 183 (100), 155 (51), 112 (53), 94 (63).
– C13H14BrN3O2: calcd. C 48.17, H 4.35, N 12.96; found C
48.11, H 4.27, N 12.83.
H 5.67, N 18.17; found C 62.46, H 5.75, N 18.07.
2-[4-(1-Hydroxy-1-methylethyl)-[1,2,3]triazol-1-yl]-
1-p-tolyl-ethanone (4g)
M. p. 155 – 158 ◦C. – 1H NMR (500 MHz, DMSO): δ =
8.14 (s, 1H, CH), 7.93 – 7.37 (m, 4H, Ar), 6.08 (s, 2H,
CH2), 5.5 (s, 1H, OH), 2.37 (s, 3H, CH3), 1.52 (s, 6H,
2CH3) ppm. – 13C NMR (125 MHz, DMSO): δ = 192.30,
145.60, 132.89, 132.59, 130.97, 130.34, 129.09, 57.01,
31.99, 22.13 ppm. – IR (KBr): ν = 3353, 1689, 1233 cm−1
.
– MS (EI, 70 eV): m/z (%) = 259.3 (3) [M]+, 244 (64), 119
(100), 105 (48), 91 (92). – C14H17N3O2: calcd. C 64.85, H
6.61, N 16.21; found C 64.78, H 6.66, N 16.31.
1-Biphenyl-4-yl-2-(4-hydroxymethyl-[1,2,3]triazole-
1-yl)ethanone (4j)
M. p. 171 – 172 ◦C. – 1H NMR (500 MHz, DMSO): δ =
8.15 (brs, 2H, Ar), 7.91 (brs, 3H, Ar), 7.79 – 7.46 (m, 5H,
Ar), 6.18 (s, 2H, CH2), 5.23 (s, 1H, OH), 4.58 (s, 2H, CH2)
ppm. – 13C NMR (125 MHz, DMSO): δ = 192.67, 146.30,
139.52, 133.87, 130.01, 129.78, 129.49, 127.94, 125.35,
1-(4-Bromophenyl)-2-(4-hydroxymethyl-[1,2,3]triazol-
1-yl)ethanone (4h)
M. p. 159 – 160 ◦C. – 1H NMR (500 MHz, DMSO): δ =
7.99 (m, 2H, Ar), 7.94 (s, 1H, CH), 7.82 (m, 2H, Ar),
6.15 (s, 2H, CH2), 5.25 (s, 1H, OH), 4.57 (s, 2H, CH2)
ppm. – 13C NMR (125 MHz, DMSO): δ = 192.49, 148.50,
134.05, 132.92, 131.01, 129.21, 125.35, 56.60, 55.94 ppm.
– IR (KBr): ν = 3347, 1696, 1229 cm−1. – MS (EI, 70 eV):
m/z (%) = 296.2 (4) [M]+, 268 (20), 266 (20), 183 (100),
155 (42), 76 (26). – C11H10BrN3O2: calcd. C 44.62, H 3.40,
N 14.19; found C 44.54, H 3.47, N 14.23.
56.61, 55.98 ppm. – IR (KBr): ν = 3288, 1689, 1232 cm−1
.
– MS (EI, 70 eV): m/z (%) = 293.3 (6) [M]+, 198 (29), 181
(100), 169 (71), 152 (96). – C17H15N3O2: calcd. C 69.61, H
5.15, N 14.33; found C 69.72, H 5.09, N 14.48.
Acknowledgement
M. M. H. is thankful to the Iran National Science Founda-
tion for partial financial assistance.
[1] L. Xu, C. Xia, L. Li, J. Org. Chem. 2004, 69, 8482.
[2] M. J. Genin, D. A. Allwine, D. J. Anderson, M. R. Bar-
bachyn, D. E. Emmert, S. A. Garmon, D. R. Graber,
K. C. Grega, J. B. Hester, D. K. Hutchinson, J. Morris,
[8] V. V. Rostovtsev, L. G. Green, V. V. Fokin, B. K. Sharp-
less, Angew. Chem. Int. Ed. 2002, 41, 2596.
[9] S. Brase, C. Gil, K. Knepper, V. Zimmermann, Angew.
Chem. Int. Ed. 2005, 44, 5188.
R. J. Reischer, C. W. Ford, G. E. Zurenko, J. C. Hamel, [10] D. Kumar, V. B. Reddy, A. Kumar, D. Mandal, R. Ti-
R. D. Schaadt, D. Stapert, B. H. Yagi, J. Med. Chem.
wari, K. Parang, Bioorg. Med. Chem. Lett. 2011, 21,
2000, 43, 953.
449.
[3] D. R. Buckle, C. J. M. Rockell, H. Smith, B. A. Spicer, [11] J. Vantikommu, S. Palle, P. S. Reddy, V. Ramanatham,
J. Med. Chem. 1986, 29, 2262.
M. Khagga, V. R. Pallapothula, Eur. J. Med. Chem.
[4] R. Alvarez, S. Velazquez, A. San-Felix, S. Aquaro,
2010, 45, 5044.
E. De Clercq, C. F. Perno, A. Karlsson, J. Balzarini, [12] D. Kumar, G. Patel, V. B. Reddy, Synlett 2009, 399.
M. J. Camarasa, J. Med. Chem. 1994, 37, 4185.
[5] J. S. Yadav, B. V. S. Reddy, G. M. Reddy, S. R. Anjum,
Tetrahedron Lett. 2009, 50, 6029.
[6] R. Huisgen, Angew. Chem., Int. Ed. Engl. 1963, 2,
565.
[13] D. Kumar, V. B. Reddy, R. S. Varma, Tetrahedron Lett.
2009, 50, 2065.
[14] K. Odlo, E. A. Hoydahl, T. V. Hansen, Tetrahedron
Lett. 2007, 48, 2097.
[15] J. Albadi, M. Keshavarz, F. Shirini, M. Vafaie-nezhad,
[7] C. W. Tornøe, C. Christensen, M. Meldal, J. Org.
Chem. 2002, 67, 3057.
Catal. Commun. 2012, 27, 17.
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Authenticated
Download Date | 6/24/15 9:17 AM

396
A. Fazeli et al. · Synthesis of 1,4-Disubstituted 1,2,3-Triazoles
[16] M. M. Heravi, L. Ranjbar, F. Derikvand, F. F. Bamohar- [22] M. M. Heravi, H. A. Oskooie, P. Kazemian, F. Derik-
ram, Catal. Commun. 2007, 8, 289.
vand, M. Ghassemzadeh, Phosphorus, Sulfur Silicon
Relat. Elem. 2004, 179, 2341.
[23] M. M. Heravi, M. Ghassemzadeh, Phosphorus, Sulfur
[17] M. M. Heravi, F. Derikvand, L. Ranjbar, F. F. Bamohar-
ram, J. Mol. Catal. A: Chem. 2007, 261, 156.
[18] M. M. Heravi, F. Derikvand, F. F. Bamoharram, J. Mol.
Catal. A: Chem. 2007, 263, 112.
Silicon Relat. Elem. 2005, 180, 347.
[24] M. Tajbakhsh,
M. M. Heravi,
A. Hosseini,
[19] M. M. Heravi, B. Alimadadi Jani, F. Derikvand,
F. F. Bamoharram, H. A. Oskooie, Catal. Commun.
2008, 10, 272.
A. Shahrezaiee, Phosphorus, Sulfur Silicon Relat.
Elem. 2003, 178, 773.
[25] H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem.
Int. Ed. 2001, 40, 2004.
[20] M. M. Heravi, A. Fazeli, H. A. Oskooie, Y. S. Be-
heshtiha, H. Valizadeh, Synlett 2012, 23, 2927.
[26] P. S. Reddy, B. Sreedhar, Synthesis 2009, 24, 4203.
[21] M. M. Heravi, S. Moghimi, Tetrahedron Lett. 2012, 53, [27] K. Konya, S. Fekete, A. Abraham, T. Patonay, Mol.
392. Divers. 2012, 16, 91.
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