Synthesis of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4- dihydropyrano[2,3-c]pyrazoles using disulfonic acid imidazolium chloroaluminate as a dual and heterogeneous catalyst

Article abstract of DOI:10.1039/c3nj00629h

In this work, disulfonic acid imidazolium chloroaluminate {[Dsim]AlCl ₄} is applied as a new acidic and heterogeneous catalyst for green, simple and efficient synthesis of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl- 1-phenyl-1,4-dihydropyrano

Full text of DOI:10.1039/c3nj00629h

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New Journal of Chemistry
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DOI: 10.1039/C3NJ00629H
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ARTICLE TYPE
Synthesis of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-
,4- dihydropyrano[2,3-c]pyrazoles using disulfonic acid imidazolium
chloroaluminate as a dual and heterogeneous catalyst
1
a
b
b
b
Ahmad Reza Moosavi-Zare, * Mohammad Ali Zolfigol, * Ehsan Noroozizadeh, Mahsa Tavasoli, Vahid
b
c
5
Khakyzadeh, Abdolkarim Zare
Received (in XXX, XXX) Xth XXXXXXXXX 20XX, Accepted Xth XXXXXXXXX 20XX
DOI: 10.1039/b000000x
In this work, disulfonic acid imidazolium chloroaluminate {[Dsim]AlCl } is applied as a new acidic and
4
heterogeneous catalyst for green, simple and efficient synthesis of 6ꢀaminoꢀ4ꢀ(4ꢀmethoxyphenyl)ꢀ5ꢀ
cyanoꢀ3ꢀmethylꢀ1ꢀphenylꢀ1,4ꢀdihydropyrano[2,3ꢀc]pyrazoles by the oneꢀpot multiꢀcomponent
condensation of aryl aldehydes with ethyl acetoacetate, malononitrile and hydrazine hydrate at 80 ºC
under solventꢀfree conditions.
1
0
Multiꢀcomponent reactions (MCRs) have a significant role in
Introduction
combinatorial chemistry as they can prepare target compounds
with higher efficacy and atom economy by formation of
structural complexity in a single step from three or more
reactants. Furthermore, MCRs present some advantages
compared with conventional chemical reactions, e.g. simplicity
In recent years, the use of ionic liquids and solid salts (with an
organic cation) as homogeneous, heterogeneous and reusable
catalysts have received massive attention in organic synthesis.
5
0
1
2
2
3
3
5
0
5
0
5
1
ꢀ3
27–30
and synthetic efficiency.
Application of these catalysts under solventꢀfree conditions often
leads to significant decreases in reaction times, increased yields,
easier workup, clean conditions and compliance with the green
chemistry protocols. With this issue in mind, we have recently
introduced a new category of ionic liquids and solid salts (with an
organic cation), namely sulfonic acid functionalized imidazolium
In this investigation, we report a highly efficient solventꢀfree
method for the synthesis of 6ꢀaminoꢀ4ꢀ(4 ꢀmethoxyphenyl)ꢀ5ꢀ
cyanoꢀ3ꢀmethylꢀ1ꢀphenylꢀ1,4ꢀdihydropyrano[2,3ꢀc]pyrazoles by
the oneꢀpot multiꢀcomponent condensation of arylaldehydes with
ethyl acetoacetate, malononitrile and hydrazine hydrate using
55
4ꢀ14
salts (SAFIS).
In this class of salts, SꢀN bond formation in
disulfonic acid imidazolium chloroaluminate {[Dsim]AlCl } as a
4
imidazole ring, as five member’s heterocyclic compounds, was
reported for the first time. These compounds have been
successfully used as catalysts or reagent to prepare
new acidic and heterogeneous catalyst (Scheme 1).
4
5
bis(indolyl)methanes, Nꢀsulfonyl imines, nitro aromatic
6
,7
8
9
compounds,
xanthenes,
1ꢀamidoalkylꢀ2ꢀnaphthols,
benzimidazoles,
1
0
11
1ꢀcarbamatoalkylꢀ2ꢀnaphthols,
4,4'ꢀ
1
2
(arylmethylene)ꢀbis(3ꢀmethylꢀ1ꢀphenylꢀ1Hꢀpyrazolꢀ5ꢀ ol)s, tertꢀ
butyl aryl carbamates and 1,2,4,5ꢀtetrasubstituted imidazoles.
In continuation of our previous projects involving the preparation
and applications of acidic ionic liquids and solid salts in organic
transformations, we have introduced disulfonic acid imidazolium
1
3
14
chloroaluminate {[Dsim]AlCl } which exhibits many interesting
4
60
properties.
Scheme 1. The condensation between aromatic aldehyde,
malononitrile, ethyl acetoacetate and hydrazine hydrate or (4ꢀ
nitrophenyl)hydrazine hydrate using [Dsim]AlCl4.
Pyranopyrazoles are an important class of heterocyclic
1
5
16
compounds; they have been used as fungicidal, bactericidal,
17
18
vasodilatory, and anticancer. These heterocycles have also
applications as pharmaceutical ingredients and biodegradable
Results and discussion
4
0
19
agrochemicals. Moreover, pyrano[2,3ꢀc]pyrazoles have been
2
0
shown to act as potential insecticidal and molluscicidal
65
Disulfonic acid imidazolium chloroaluminate was prepared in
two steps. Initially, ionic liquid disulfonic acid imidazolium
chloride {[Dsim]Cl} was synthesized according to our previous
21,22
agents.
Consequently, considerable attention has been focused
on the development of new procedures for the preparation of
8
2
3ꢀ26
report, by the reaction of imidazole (1 eq.) with chlorosulfonic
4
5
these compounds.
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acid (2 eq.). Then, [Dsim]AlCl was prepared by the reaction of
35
4
[
Dsim]Cl (1 eq.) with aluminum chloride (1 eq.) with high atomic
1
2
economy.
a)
XRD pattern of the catalyst {[Dsim]AlCl } was studied and
exhibited a broadened pattern due to its nonꢀcrystal at 2θ = 15ꢀ35
4
◦
5
(Figure 1).
Figure 1. The XRD pattern of [Dsim]AlCl4.
In another investigation, the SEM micrographs of the catalyst
showed that the particles have not completely agglomerated.
Some particles of the catalyst were observed in nano and micro
scales [Figure 2 (a and b)].
10
b)
To optimize the reaction conditions, as a model reaction, the
condensation between hydrazine hydrate (2.5 mmol) ethyl
acetoacetate (2 mmol), malononitrile (2 mmol) and 4ꢀ
chlorobenzaldehyde (2 mmol) was studied in the presence of
15
different amounts of [Dsim]AlCl at range of 50ꢀ120 °C in the
4
absence of solvent (Table 1). As it is shown in Table 1, the
reaction was efficiently performed using 7 mol% of the catalyst at
80 °C to give the desired product in high yield within short
reaction time (Table 1, entry 2). The reaction was also examined
at 80 °C without catalyst under solventꢀfree conditions in which
the reaction did not significantly progress even after long reaction
time (Table 1, entry 5).
20
25
Table 1. Effect of different amounts of the catalyst and
temperature on the reaction of hydrazine hydrate (2.5 mmol) with
ethyl acetoacetate (2 mmol), malononitrile (2 mmol) and 4ꢀ
chlorobenzaldehyde (2 mmol) in the absence of solvent.
Figure 2. The SEM images of the catalyst in micro size (a) and in
nano size (b)
40
Table 2. The reaction of hydrazine hydrate (2.5 mmol) with ethyl
acetoacetate (2 mmol), malononitrile (2 mmol) and 4ꢀ
a
Entry
Mol% of
Catalyst
Temp.
(°C)
Time (min)
Yield (%)
chlorobenzaldehyde (2 mmol) using [Dsim]AlCl (7 mol%) in
4
different solvents (5 mL) under reflux conditions.
1
2
7
7
50
80
8
1
75
92
a
Entry
Solvent
Time (min)
Yield (%)
3
4
5
6
7
8
9
7
7
100
120
80
1
1
92
92
28
50
65
92
92
1
2
EtOH
60
60
30
40
ꢀ
90
5
CH
CH
CH
Acetone
3
CN
3
80
5
80
3
3
4
5
3
OH
60
60
60
50
20
40
7
80
1
2
Cl
2
10
80
1
a
Isolated yield.
a
Isolated yield.
30
45
In the next step, the model reaction was examined in several
As Table 2 indicates, solution conditions were not efficient,
and afforded the product in low yields. Increasing the reaction
times did not improve the yields.
solvents using 7 mol% of [Dsim]AlCl in reflux conditions. The
results are depicted in Table 2.
4
To assess the efficacy and generality of [Dsim]AlCl in the
4
2
| Journal Name, [year], [vol], 00–00
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synthesis of 6ꢀaminoꢀ4ꢀ(4ꢀmethoxyphenyl)ꢀ5ꢀcyanoꢀ3ꢀmethylꢀ1ꢀ
phenylꢀ1,4ꢀdihydropyrano[2,3ꢀc]pyrazoles, various arylaldehydes
including benzaldehyde, and arylaldehydes aldehydes possessing
electronꢀreleasing substituents, electronꢀwithdrawing substituents
and halogens on their aromatic ring) were reacted with hydrazine
hydrate, ethyl acetoacetate and malononitrile under the optimal
reaction conditions to afford the corresponding products in high
yields and in short reaction times. The results are summarized in
Table 3.
Table 3. (Continued)
a
(
Entry
Product
Time
Yield
(%)
Mp. ºC (Lit.)
227ꢀ229
(
min)
5
8
7
85
2
6
(191 )
2
44ꢀ246
1
0
Table 3. The preparation of 6ꢀaminoꢀ4ꢀ(4 ꢀmethoxyphenyl)ꢀ5ꢀ
9
1
5
90
85
2
3
5
(
214ꢀ216
)
)
cyanoꢀ3ꢀmethylꢀ1ꢀphenylꢀ1,4ꢀ
dihydropyrano[2,3ꢀc]pyrazoles
using [Dsim]AlCl as catalyst at 80 ºC.
4
a
246ꢀ248
223ꢀ225
Entry
1
Product
Time (min)
1
Yield
%)
Mp. ºC
(Lit.)
1
1
0
1
2
(
(
2
64ꢀ266
2
3
4
(
244ꢀ246
)
)
90
92
88
85
1
5
85
85
215ꢀ217
206ꢀ208
2
45ꢀ247
2
(
234ꢀ236
2
3
4
1
3
3
1
1
2
3
2
61ꢀ263
2
4
(
145ꢀ147
)
259ꢀ261
1
88
75
240ꢀ242
5
6
5
82
260ꢀ263
b
c
1
4
60
266
2
40ꢀ242
7
3
80
85
2
4
5
a
b
(
235ꢀ237
)
)
Isolated yield. The product was produced by the reaction of
hydrazine hydrate (5 mmol) with ethyl acetoacetate (4 mmol),
malononitrile (4 mmol) and terephthaldehyde (2 mmol) in the
30
2
62ꢀ264
c
absence of solvent. In this temprature, the product was
2
7
(248ꢀ249
tot
decomposed.
In
35 acetoacetate is activated by [Dsim]AlCl
attacks to the activated carbonyl group of ethyl acetoacetate. Loss
of one molecule of H O, and intramolecular nucleophillic attack
a
plausible mechanism (Scheme 2), initially, ethyl
a
Isolated yield.
4
, and then hydrazine
In another investigation, the condensation of arylaldehyde with
2
by another NH group of hydrazine to the next carbonyl group of
ethyl acetoacetate (which acticted by the catalyst) affords 5ꢀ
methylꢀ2,4ꢀdihydroꢀpyrazolꢀ3ꢀone (I). Sulfonic acid groups of the
1
2
2
5
0
5
malononitrile, ethyl acetoacetate and (4ꢀnitrophenyl)hydrazine
hydrate using [Dsim]AlCl4 was studied wherein the
corresponding products were produced in high yields and short
reaction times (Table 3, entries 11, 12 and13). Interestingly, the
condensation of hydrazine hydrate (5 mmol) ethyl acetoacetate (4
mmol), malononitrile (4 mmol) and terephthaldehyde (2 mmol) at
2
4
0
catalyst cation can be deprotonated with AlCl anion and the
4
intermediate structure of the catalyst (in equilibrium with the first
structure of the catalyst) can be produced. Meanwhile, the
deprotonated cation has another sulfonic acid functional group
8
0
°C under solventꢀfree conditions afforded 4,4'ꢀ(1,4ꢀ
45
which can be catalyzed the reaction. AlCl anion can be produced
phenylene)bis(6ꢀaminoꢀ3ꢀmethylꢀ2,4ꢀdihydropyrano[2,3ꢀ
c]pyrazoleꢀ5ꢀcarbonitrile) (15) in 78 % yield within 60 min
4
Cl anion and AlCl3 during the reaction. Malononitrile is
coordinated and activated by AlCl . Cl anion and AlCl anion
(Table 3, entry 14). Thus, the catalyst was general and highly
3
4
react to activated form of malononitrile (II, II', II'') as a base to
give III after reaction with aldehyde and removing one molecule
efficient.
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DOI: 10.1039/C3NJ00629H
of H O.
2
AlCl4
AlCl4
AlCl4
AlCl4
O
O
O
O
O
S O
O
O
N
O
N
N
N
N
N
N
N
S
S
O
S
S
O
S
S
O
S
O
O
O
O
O
O
O
O
O
O
O
O
H
H
H
H
H
H
H
H
N
OH
OH
N
O
H
O
O
O
O
- H O
O
- EtOH
2
H
N
N
N
O
O
O
O
I
H
H
NH2
NH2
NH2
H N NH2
2
O
O
O
S
N
O
O
H
O
H
H
S
S
O
O
O
O
O
N
N
N
S
O
O
H Cl
AlCl3
AlCl4
H
Cl
AlCl3
N
N
O
S
S
H
O O
H
O
O
O
O
S
O
N
H
O
H Cl
Cl
Cl
N
O
Cl
H
H
Cl
Cl
Cl
H
Cl
S
Cl
Cl
H
Cl
Cl
Cl
Cl
Cl
H
O
Al
N
Al
Al
N
Al
N
Al
N
O
O
N
AlCl3
N
O
or
H
Ar or
C
H
Ar
Ar
H
H
H
CN
NC
H
CN
CN
Cl
NC
H
II'
II''
II
H
H
CN
- H2O
O
S
N
O
H
O
H
CN
CN
AlCl4
Cl AlCl3
Ar
N
O
III
S
H
O
O
O
S
H O
CN
O
H
N
AlCl4
C
N
III
H
H
O
O
AlCl4
N
H
O
Ar
H
Ar
O
N
Ar
H
S
S
N
CN
O
CN
H
O
H
O
H
N
N
AlCl4
N
H
H
N
N
N
O
N
O
NH2
N
O
O
O
H
O
H
N
H
S
H
O
H
O
O
O
S
S
O
N
N
O
I
5
Scheme 2. The proposed mechanism for the synthesis of 6ꢀaminoꢀ4ꢀ(4ꢀmethoxyphenyl)ꢀ5ꢀcyanoꢀ3ꢀmethylꢀ1ꢀphenylꢀ1,4ꢀ
dihydropyrano[2,3ꢀc]pyrazoles.
Finally, addition of I to III in the presence of [Dsim]AlCl4 15 these cases, the results were not similar to [Dsim] AlCl4.
followed by intramolecular nucleophillic attack, can give the
expected pyranopyrazole.
Obtained results from this study showed dual activity of [Dsim]
AlCl . Also, [Msim] Cl as an acidic ionic liquid and H SO as a
10
4
2
4
traditional catalyst were tested in the reaction in order to get a
In another study, to confirm the dual application of [Dsim] AlCl4,
we studied the model reaction in the presence of some other
species which can be presented in this reaction condition such as
direct comparison with [Dsim] AlCl which afforded lower yields
4
20
of the products in longer reaction times (Table 4, Entries 1 and 6).
[
Dsim]Cl, HCl, AlCl , [Dsim] Cl/ AlCl (Table 4, Entries 2ꢀ5). In
3 3
4
| Journal Name, [year], [vol], 00–00
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Table 4. The reaction of hydrazine hydrate (2.5 mmol) with ethyl
Experimental
acetoacetate (2 mmol), malononitrile (2 mmol) and 4ꢀ
chlorobenzaldehyde (2 mmol) using different catalysts (7 mol%)
under solventꢀfree conditions.
40
All chemicals were purchased from Merck or Fluka Chemical
Companies. The known products were identified by comparison
of their melting points and spectral data with those reported in the
literature. Progress of the reactions was monitored by TLC using
5
a
Entry
Catalyst
[Msim]Cl
[Dsim]Cl
Time (min)
Yield (%)
1
13
silica gel SIL G/UV 254 plates. The H NMR (400 MHz) and
C
1
2
3
4
5
6
4
2
80
85
70
75
53
87
45
NMR (100 MHz) were run on a Bruker Avance DPXꢀ250 FTꢀ
NMR spectrometer (δ in ppm). Mass spectra were recorded on a
Shimadzu GC MSꢀQP 1000 EX 85 apparatus. Infrared spectrum
of products is recorded by Perkin Elmer PEꢀ1600ꢀFTIR. Melting
points were recorded on a Büchi Bꢀ545 apparatus in open
capillary tubes.
AlCl
3
6
[Dsim]Cl/AlCl
3
(1/1)
10
3
HCl
50
H
2
SO
4
5
a
2.1. Preparation of 1,3-disulfonic acid imidazolium
Isolated yield.
tetrachloroaluminate {[Dsim]AlCl }:
4
Recyclability of the catalyst was examined upon the
A roundꢀbottomed flask (50 mL) was charged with 1,3ꢀdisulfonic
acid imidazolium chloride (1.323 g, 5mmol), and then AlCl3
condensation of hydrazine hydrate (2.5 mmol) with ethyl
acetoacetate (2 mmol), malononitrile (2 mmol) and 4ꢀ
chlorobenzaldehyde (2 mmol). After completion of the reaction,
the reaction mixture was extracted with warm ethanol (20 mL) to
separate the catalyst (the product is soluble in warm ethanol;
however, the catalyst is not soluble in this solvent). Then, ethanol
was evaporated and the solid residue (crude product) was
triturated by a mixture of ethanol and water (9/1) to give the pure
product. The recovered catalyst was washed with EtOAc (2×20
1
1
2
0
5
0
5
5
(0.6667 g, 5 mmol) was added over a period of 5 min at 50 °C.
Afterward, the reaction mixture was stirred for 30 min at 50 °C to
1
2
give [Dsim]AlCl as a white powder in 98% yield, 1.95 g.
4
2
.1.1. Spectral data of [Dsim]AlCl4:
White powder, mp 395ºC (dec.); IR (KBr) 629, 1051, 1127, 1200,
−
1 1
mL), dried at 90 ºC under vacuum condition, and reused for the 60 1315, 2950ꢀ3400 cm ; H NMR (300 MHz, DMSOꢀd
): δ (ppm)
6
13
preparation of 6ꢀaminoꢀ4ꢀ(4 ꢀmethoxyphenyl)ꢀ5ꢀcyanoꢀ3ꢀmethylꢀ
1ꢀphenylꢀ1,4ꢀdihydropyrano[2,3ꢀc]pyrazoles according to the
mentioned procedure. The catalyst was recovered and reused for
four times without any significant changes in the yield and the
reaction time (Table 5).
7.66 (s, 2H), 9.06 (s, 1H), 14.37 (s, 1H); C NMR (75 MHz,
+
DMSOꢀd
(M ).
): δ (ppm) 119.8, 134.8; MS: m/z = 399 (M +1), 398
6
+
2
.2. General procedure for the synthesis of 6-amino-4-(4 -
65
methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-
dihydropyrano[2,3-c]pyrazoles (1-15)
Table 5. The reaction between hydrazine hydrate (2.5 mmol),
ethyl acetoacetate (2 mmol), malononitrile (2 mmol) and 4ꢀ
chlorobenzaldehyde (2 mmol) in the presence of reused
2
5
A mixture of aromatic aldehyde (2 mmol), malononitrile (0.132
g, 2 mmol), ethyl acetoacetate (0.26 g, 2 mmol) hydrazine
[
Dsim]AlCl (7 mol%) at 80 ºC under solventꢀfree conditions.
4
hydrate (2.5 mmol) and [Dsim]AlCl (0.14 mmol) was added to a
4
a
Entry
Cycle
Time (min)
Yield (%)
70 test tube, and stirred at 80 ºC. After the completion of the
reaction, as monitored by TLC, the reaction mixture was cooled
to room temperature, extracted with warm ethanol (20 mL) to
separate the catalyst (the product is soluble in warm ethanol;
however, the catalyst is not soluble in this solvent). Then, the
ethanol was evaporated and the solid residue (crude product) was
triturated by a mixture of ethanol and water (9/1) to give the pure
product. The recovered catalyst was washed with EtOAc (2×20
mL), dried at 90 ºC under vacuum, and reused.
st
1
2
3
4
1 run
1
2
4
5
92
90
89
87
st
2 run
st
75
3 run
st
4 run
a
Isolated yield.
Acknowledgements
Conclusions
8
0
The authors gratefully acknowledge partial support of this work
by the Research Affairs Office of BuꢀAli Sina University (Grant
number 32ꢀ1716 entitled development of chemical methods,
reagents and molecules), and Center of Excellence in
Development of Chemical Method (CEDCM), Hamedan, I.R.
Iran.
3
0
In summary, we have reported the efficient synthesis of
ꢀaminoꢀ4ꢀ(4 ꢀmethoxyphenyl)ꢀ5ꢀcyanoꢀ3ꢀmethylꢀ1ꢀphenylꢀ1,4ꢀ
dihydropyrano[2,3ꢀc]pyrazoles using disulfonic acid imidazolium
6
chloroaluminate {[Dsim]AlCl } as a dual, heterogeneous and
4
reusable catalyst in a green media. The promising points for the
presented methodology are efficiency, generality, high yield,
relatively short reaction time, low cost, cleaner reaction profile,
ease of product isolation, simplicity, and finally compliance with
the green chemistry protocols.
85
3
5
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2
7
J. Zhu, H. Bienayme, Multicomponent Reactions, Eds., Wiley,
Weinheim, 2005.
Notes and references
7
7
0
5
a
28 A. Hasaninejad, A. Zare, M. Shekouhi and J. Ameri Rad, J. Comb.
Chem, 2010, 12, 844.
2
University of Sayyed Jamaleddin Asadabadi, Asadabad, 6541835583,
Iran, E-mail: moosavizare@yahoo.com
9
A. Khazaei, M.A. Zolfigol, A.R. MoosaviꢀZare, A. Zare, A. Parhami
and A. Khalafiꢀ Nezhad, Appl. Catal. A: Gen, 2010, 386, 179.
b
Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683,
5
0
5
0
5
0
5
0
5
0
5
0
5
Iran, E-mail: mzolfigol@yahoo.com
30 A. Khazaei, M. A. Zolfigol, A. R. MoosaviꢀZare, A. Zare, M.
Khojasteh, Z. Asgari, V. Khakyzadeh and A. Khalafiꢀ Nezhad, Catal.
Commun, 2012, 20, 54.
c
Department of Chemistry, Payame Noor University, 19395-4697 Tehran,
Iran
†
Electronic Supplementary Information (ESI) available: [details of any
1
1
2
2
3
3
4
4
5
5
6
6
supplementary information available should be included here]. See
DOI: 10.1039/b000000x/
1
2
J. P. Hallett and T. Welton, Chem. Rev, 2011, 111, 3508.
N. P. Tarasova, Yu. V. Smetanniko and A. A. Zanin, Russ. Chem.
Rev, 2010, 79, 463.
M.A.P. Martins, C.P. Frizzo, D.N. Moreira, N. Zanatta and H.G.
Bonacorso, Chem. Rev, 2008, 108, 2015.
M. A. Zolfigol, A. Khazaei, A. R. MoosaviꢀZare and A. Zare, Org.
Prep. Proced. Int, 2010, 42, 95.
M. A. Zolfigol, A. Khazaei, A. R. MoosaviꢀZare and A. Zare, J.
Iran. Chem. Soc, 2010, 7, 646.
A. Khazaei, M. A. Zolfigol, A. R. MoosaviꢀZare and A. Zare, Sci.
Iran., Trans. C, 2010, 17, 31.
M. A. Zolfigol, A. Khazaei, A. R. MoosaviꢀZare, A. Zare, H. G.
Kruger, Z. Asgari, V. Khakyzadeh and M. KazemꢀRostami, J. Org.
Chem, 2012, 77, 3640.
M.A. Zolfigol, A. Khazaei, A.R. MoosaviꢀZare, A. Zare and V.
Khakyzadeh, Appl. Catal. A, Gen. 2011, 400, 70.
A. Khazaei, M. A. Zolfigol, A. R. MoosaviꢀZare, A. Zare, E.
Ghaemi, V. Khakyzadeh, Z. Asgari and A. Hasaninejad, Sci. Iran.,
Trans. C, 2011, 18, 1365.
3
4
5
6
7
8
9
1
1
1
1
0
1
2
3
M.A. Zolfigol, V. Khakyzadeh, A.R. MoosaviꢀZare, A. Zare, S.B.
Azimi, Z. Asgari and A. Hasaninejad, C. R. Chim. 2012, 15, 719.
A. Zare, T. Yousofia and A.R. MoosaviꢀZare, RSC. Adv, 2012, 2,
7988.
A. Khazaei, M.A. Zolfigol, A.R. MoosaviꢀZare, Z. Asgari, M.
Shekouhy, A. Zare and A. Hasaninejad,. RSC. Adv, 2012, 2, 8010.
M.A. Zolfigol, V. Khakyzadeh, A. R. MoosaviꢀZare, G. Chehardoli,
F. DerakhshanꢀPanah, A. Zare and O. Khaledian, Sci. Iran., Trans. C,
2012, 19, 1584.
1
1
4
5
M. A. Zolfigol, A. Khazaei, A. R. MoosaviꢀZare, A. Zare, Z. Asgari
and V. Khakyzadeh, A. Hasaninejad, J. Ind. Eng. Chem, 2013, 19,
7
21.
A. Feurer, J. Luithle, S. Wirtz, G. Koenig, J. Stasch, E. Stahl, R.
Schreiber, F. Wunder, D. Lang, PCT Int. Aool. Wo 2004009589,
Baye Healtheare Ag, Germany.
1
1
1
6
7
8
M.N. Nasr and M.M. Gineinah, Arch. Pharm. Med. Chem, 2002,
3
35, 289.
V.K. Ahluwalia, A. Dahiya and V. Garg, Indian J. Chem, 1997, 36B,
88.
M.R. Nadia, Y.K. Nahed, A.A. Fahmyb and A.A. F. ElꢀSayeda, Der
Pharma Chem, 2010, 2, 400.
1
2
9
0
H. Junek and Aigner, Chem. Ber, 1973, 106, 914.
E.S. ElꢀTamany, F.A. ElꢀShahed and B.H. Mohamed, J. Serb. Chem.
Soc, 1999, 64, 9.
2
2
1
2
F.M. Abdelrazek, P. Metz, N.H. Metwally and S.F. ElꢀMahrouky,
Arch. Pharm, 2006, 339, 456.
A. Siddekha, A. Nizam and M. A. Pasha, Spectrochim Acta Part B,
2
011, 81, 431.
23 H. V. Chavan, S. B. Babar, R. U. Hoval, and B. P. Bandgar, Bull.
Korean Chem. Soc, 2011, 32, 3963.
2
4
H. Mecadon, M. R. Rohman, M. Rajbangshi, B. Myrboh and
Tetrahedron Lett, 2011, 52, 2523.
2
5
S. R. Mandha, S. Siliveri, M. Alla, V. R. Bommena, M. R.
Bommineni, and S. Balasubramanian, Bioorg. Med. Chem. Lett,
2
012, 22, 5272.
2
6
M. Bihani, P. P. Bora and G. Bez, Journal of Chemistry, 2013,
9
20719.
6
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