Catalytic application of 1-(carboxymethyl)pyridinium iodide on the synthesis of pyranopyrazole derivatives

Article abstract of DOI:10.1016/j.molcata.2016.02.003

In this investigation, acetic acid functionalized pyridinium salt, namely 1-(carboxymethyl)pyridinium iodide {[cmpy]I}, has been introduced as reusable catalyst for green, simple and efficient synthesis of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-ph

Full text of DOI:10.1016/j.molcata.2016.02.003

Journal of Molecular Catalysis A: Chemical 415 (2016) 144–150
Contents lists available at ScienceDirect
Journal of Molecular Catalysis A: Chemical
journal homepage: www.elsevier.com/locate/molcata
Catalytic application of 1-(carboxymethyl)pyridinium iodide on the
synthesis of pyranopyrazole derivatives
Ahmad Reza Moosavi-Zare , Mohammad Ali Zolfigolb,∗, Rasoul Salehi-Moratabb,
a,∗
Ehsan Noroozizadehb
a
Sayyed Jamaleddin Asadabadi University, Asadabad 6541835583, I. R. Iran
Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, I. R. Iran
b
a r t i c l e i n f o
a b s t r a c t
Article history:
In this investigation, acetic acid functionalized pyridinium salt, namely 1-(carboxymethyl)pyridinium
Received 12 December 2015
Received in revised form 13 January 2016
Accepted 1 February 2016
Available online 3 February 2016
iodide {[cmpy]I}, has been introduced as reusable catalyst for green, simple and efficient synthesis of
6
-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles by the
one-pot tandem four-component condensation reaction of aryl aldehydes with ethyl acetoacetate, mal-
◦
1
13
ononitrile and hydrazine hydrate at 100 C under solvent-free conditions. Additionally, H and C NMR,
mass, CHN analysis, Fourier transform infrared spectroscopy (FT-IR), scanning electron microscope (SEM),
thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), X-ray diffraction analysis
Keywords:
Pyranopyrazole
Tandem reaction
(XRD), and calculation of crystallite size and inter planer distance of the catalyst have been investigated.
©
2016 Elsevier B.V. All rights reserved.
1
-(Carboxymethyl)pyridinium iodide
Solvent-free
1
. Introduction
Tandem reaction, as a modern protocol in organic transforma-
focused on the development of new protocols for the preparation
of these compounds.
Recently, we have introduced a new category of ionic liq-
uids and solid salts (with an organic cation), namely sulfonic acid
functionalized imidazolium salts (SAFIS) [23–33]. In this class of
salts, S N bond formation in imidazole ring, as five member’s
heterocyclic compounds, was reported for the first time. These
compounds have been successfully applied as catalysts or reagent
for the synthesis of bis(indolyl) methanes [23], N-sulfonyl imines
[24], 1-amidoalkyl-2-naphthols [25], various xanthene derivatives
tions, is a reaction in which several bonds are formed in some
sequences without separating of any intermediates, changing reac-
tion conditions and adding reagents. Clean reaction condition, high
atomic economy and much complexity in one step are some impor-
tant advantages of tandem reactions [1–5].
Pyranopyrazoles are interesting class of heterocyclic com-
pounds; they have been used as fungicidal [6], bactericidal [7],
vasodilatory [8] and anticancer [9]. They have also reported as
pharmaceutical ingredients and biodegradable agrochemicals [10].
Additionally, pyrano[2,3-c]pyrazoles have been acted as potential
insecticidal [11] and molluscicidal agents [12,13]. Several cata-
lysts have been introduced for the synthesis of pyranopyrazoles,
including imidazole [13], per-6-amino-b-cyclodextrin [14], phase
transfer catalyst (HDBAC) [15], organocatalysts (MDOs) [16], d,l-
Proline [17], hexa decyl tri methyl ammonium bromide (HTMAB)
ꢀ
[26], 1-carbamatoalkyl-2-naphthols [27], 4,4 -(arylmethylene)-
bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s [28], N-boc protected
amines [29], hexahydroquinolines [30], nitroaromatic compounds
[31,32], 1,2,4,5-tetrasubstituted imidazoles [33]. In continua-
tion of our previous projects involving the preparation and
applications of acidic ionic liquids and solid salts in organic trans-
formations, we have used 1-(carboxymethyl) pyridinium iodide
{[cmpy]I} on the synthesis of 6-amino-4-(4-methoxyphenyl)-5-
cyano-3-methyl-1-phenyl-1, 4-dihydropyrano[2,3-c]pyrazoles by
the one-pot multi-component condensation reaction of arylaldehy-
des with ethyl acetoacetate, malononitrile and hydrazine hydrate
[
[
18], disulfonic acid imidazolium chloroaluminate {[Dsim]AlCl }
4
19], gamma-alumina [20], magnetic Fe O nanoparticles [21] and
3
4
isonicotinic acid [22]. Therefore, considerable attention has been
(Scheme 1).
∗ Corresponding authors. Fax: +98 811 8272404.
E-mail addresses: moosavizare@yahoo.com (A.R. Moosavi-Zare),
mzolfigol@yahoo.com (M.A. Zolfigol).
http://dx.doi.org/10.1016/j.molcata.2016.02.003
1
381-1169/© 2016 Elsevier B.V. All rights reserved.

A.R. Moosavi-Zare et al. / Journal of Molecular Catalysis A: Chemical 415 (2016) 144–150
145
Scheme 1. The preparation of pyranopyrazole derivatives using [cmpy]I.
Scheme 2. The synthesis of 1-(carboxymethyl) pyridinium iodide {[cmpy]I}.
Fig. 1. The XRD pattern of 1-(carboxymethyl) pyridinium iodide [cmpy]I.
2
. Experimental
2.3. General procedure for the synthesis of
6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-
2.1. General
dihydropyrano[2,3-c]pyrazoles
All chemicals were purchased from Merck or Fluka Chemical
A mixture of aromatic aldehyde (2 mmol), malononitrile
(0.132 g, 2 mmol), ethyl acetoacetate (0.26 g, 2 mmol) hydrazine
hydrate (2.5 mmol) and {[cmpy]I (10 mol%) was added in a 10 mL
round-bottomed flask connected to a reflux condenser, and stirred
at 100 C. After completion of the reaction, as monitored by TLC,
H O (10 mL) was added to the reaction mixture, stirred and refluxed
2
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
1
◦
using silica gel SIL G/UV 254 plates. The H NMR (400 MHz) and
13
C NMR (100 MHz) were recorded on a Bruker Avance DPX-250
FT-NMR spectrometer (ı in ppm). Infrared spectrum of products
was recorded by PerkinElmer PE-1600-FTIR. Melting points were
recorded on a Büchi B-545 apparatus in open capillary tubes.
for 5 min. Then the reaction mixture was filtered and the solvent of
the filtrate (H O) was removed under reduced pressure to separate
2
the catalyst from crude product. The solid residue (crude product)
was triturated by a mixture of ethanol and water (9/1) to obtain the
pure product.
2
.2. Procedure for the synthesis of 1-(carboxymethyl) pyridinium
3
. Results and discussion
iodide {[cmpy]I}
1
-(Carboxymethyl)pyridinium iodide {[cmpy]I} was synthe-
A mixture of pyridine (0.010 mol) and ethyl iodoacetate
◦
sized by the reaction of pyridine with ethyl iodoacetate at 70 C.
Then, the product was hydrolysed to give [cmpy]I. The structure of
◦
(
0.010 mol) was stirred and heated at 70 C for 24 h. After this time,
the reaction mixture turned to a dark viscous liquid. The liquid was
1
13
[
cmpy]I was confirmed by HNMR, CNMR, IR and mass as well as
washed with diethyl ether (3 × 30 mL) and dried under vacuum for
CHN analysis (Scheme 2).
2
h. Then, a solution of HCl 37% (0.011 mol) was added to prepare
The IR spectrum of [cmpy]I has been shown in Fig. S1. The broad
liquid and refluxed for 30 min. Finally, the solvent was removed
under reduced pressure and the remaining solid was washed with
diethyl ether to give the product as a yellowish powder.
−1
peak at 2493–3050 cm can be related to O H stretching of the
COOH group. Also, the peak observed at 1734 cm correspond to
vibrational modes of C O bond of the COOH group. Also, the C H
−1

1
46
A.R. Moosavi-Zare et al. / Journal of Molecular Catalysis A: Chemical 415 (2016) 144–150
stretching vibrations of pyridine ring in 1-(carboxymethyl) pyri-
−
1
dinium iodide observed at 3050 cm and C H bending vibrations
−
1
of pyridine ring in [cmpy]I appeared at 692 and 888 cm . These
mentioned peaks clearly confirmed the structure of [cmpy]I.
The structure of [cmpy]I was also studied by NMR studies. The
1
important peak in H NMR spectra of the [cmpy]I was related to the
acidic hydrogen of COOH which was observed at 14.06 ppm (Fig.
1
3
S2). Moreover, in C NMR spectra of [cmpy]I, the peaks related to
methylene group and carbonyl group were observed at 60.56 and
1
67.66 ppm respectively. The peaks related to pyridine ring were
seen at 127.12, 146.15 and 146.74 ppm (Fig. S3).
X-ray diffraction analysis (XRD) pattern of 1-(carboxymethyl)
◦
pyridinium iodide {[cmpy]I} was studied in a domain of 0–90
(
Fig. 4). As it is shown at Fig. 1, indicates that XRD pattern
exhibited diffraction lines of a high crystalline nature at about
◦
◦
◦
◦
◦
◦
◦
2
ꢀ ≈ 18.8 , 19.6 , 23.0 , 24.0 , 26.0 , 27.4 and 28.8 . Crystallite size
was calculated by Debye–Scherrer’s formula given by equation:
D = K ꢁ/(ˇ cos ꢀ). The crystallite size obtained using this formula
◦
was at about 32.49 nm (for the highest diffraction line at 24.0 )
and inter planer distance was calculated via the Bragg equa-
tion:dhkl = ꢁ/(2sin ꢀ), which obtained 0.3703 nm (ꢁ:Cu radiation
0.154178 nm).
In another investigation, the scanning electron microscope
SEM) micrographs of the catalyst were studied. The SEM
(
Fig. 2. The SEM images of 1-(carboxymethyl) pyridinium iodide [cmpy]I.
images showed that the particles have not completely agglom-
erated. Moreover, particles of the catalyst were observed in
nano size which is in good agreement with calculated size by
Debye–Scherrer’s equation (Fig. 2) provided the presence of the
expected elements in the structure of the catalyst, namely carbon,
oxygen, nitrogen and iodide. Therefore, the structure of the catalyst
was completely confirmed by EDX analyze.
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 4-chlorobenzaldehyde (2 mmol) in the absence of solvent.
◦
Yielda (%)
Entry
Mol% of catalyst
Temp. ( C)
Time (min)
10
5
3
Thermal gravimetric analysis (TGA) of the 1-(carboxymethyl)
pyridinium iodide {[cmpy]I} was also studied. The corresponding
diagrams are shown in Fig. 4. The thermogravimetry (TG) and dif-
ferential thermal gravimetric (DTG) of the catalyst showed weight
1
2
3
4
5
6
7
8
9
10
10
10
10
–
5
7
10
15
60
80
65
78
93
92
Trace
72
72
93
93
100
120
100
100
100
100
100
3
◦
losses in two steps. [cmpy]I was decomposed after 286 C.
45
10
10
4
To optimize the reaction conditions, the condensation between
hydrazine hydrate (2.5 mmol) ethyl acetoacetate (2 mmol), mal-
ononitrile (2 mmol) and 4-chlorobenzaldehyde (2 mmol), as a
model reaction, was investigated in the presence of different
5
a
◦
Isolated yield.
amounts of [cmpy]I at range of 60–120 C in the absence of sol-
vent (Table 1). Energy-dispersive X-ray spectroscopy (EDX) from
Fig. 3. Energy-dispersive X-ray spectroscopy (EDX) of 1-(carboxymethyl) pyridinium iodide [cmpy]I.

A.R. Moosavi-Zare et al. / Journal of Molecular Catalysis A: Chemical 415 (2016) 144–150
147
Fig. 4. TG/DTG diagrams of 1-(carboxymethyl) pyridinium iodide [cmpy]I.
Table 2
The reaction of hydrazine hydrate (2.5 mmol) with ethyl acetoacetate (2 mmol), mal-
ononitrile (2 mmol) and 4-chlorobenzaldehyde (2 mmol) using [cmpy]I (10 mol%) in
different solvents (5 mL) under reflux conditions.
Entry
Solvent
Time (min)
Yielda (%)
1
2
3
4
5
–
H2O
Acetinitrile
Ethanol
CH2Cl2
3
5
60
60
30
93
72
40
45
23
a
Isolated yield.
To investigate the efficacy and generality of [cmpy]I in the
synthesis of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-
phenyl-1,4-dihydropyrano[2,3-c]pyrazoles, various arylaldehydes
(including benzaldehyde, and arylaldehydes aldehydes possess-
ing electron-releasing substituents, electron-withdrawing sub-
stituents and halogens on their aromatic ring) were reacted with
hydrazine hydrate, ethyl acetoacetate and malononitrile under the
optimal reaction conditions to obtain the desired products in high
yields and in short reaction times. The results are displayed in
Table 3.
In a plausible mechanism, initially, ethyl acetoacetate was acti-
vated by [cmpy]I and hydrazine attacked to the carbonyl group of
the activated ethyl acetoacetate. Then, loss of H O, and intramolec-
2
ular nucleophillic attack by another NH2 group of hydrazine to
the next carbonyl group of ethyl acetoacetate afforded 5-methyl-
2
, 4-dihydro-pyrazol-3-one and removed EtOH. In the next step,
by the reaction of aromatic aldehyde, which was activated by
cmpy]I, with malononitrile, cyanoolefin compound was prepared.
Finally, by the tandem Michael addition–cyclization reaction of
-methyl-2,4-dihydro-pyrazol-3-one with cyanoolefin compound
[
5
the desired pyranopyrazole was prepared (Scheme 3).
Scheme 3. The plausible mechanism for the synthesis of pyranopyrazoles.
In another investigation, recyclability of the catalyst was
examined upon the reaction of hydrazine hydrate (2.5 mmol)
with ethyl acetoacetate (2 mmol), malononitrile (2 mmol) and 4-
chlorobenzaldehyde (2 mmol). After completion of the reaction,
the obtained nanoparticles (Fig. 3). As it is shown in Table 1, the
reaction was efficiently performed using 10 mol% of the catalyst at
◦
1
00 C to give the desired product in high yield within short reac-
H O was added to the reaction mixture, stirred and refluxed for
2
◦
tion time (Table 1, entry 3). The reaction was also tested at 100 C
without catalyst under solvent-free conditions in which the reac-
tion did not significantly progress even after long reaction time
5 min. Then the reaction mixture was filtered and the solvent of
the filtrate (H O) was removed under reduced pressure to separate
2
the catalyst from crude product. Finally, the reused catalyst was
used for another reaction. We observed that the catalytic activity
of the catalyst was restored within the limits of the experimental
errors for eight successive runs (Fig. 5). In this method, in order
to reuse of the catalyst, unreacted hydrazine hydrate is miscible in
water and is separated with catalyst.
(Table 1, entry 5).
In the next step, the model reaction was examined in several sol-
vents using 10 mol% of [cmpy]I under reflux conditions. The results
are depicted in Table 2. As it is shown in Table 2, indicates that the
solvent-free conditions are more effective than solvent conditions.

1
48
A.R. Moosavi-Zare et al. / Journal of Molecular Catalysis A: Chemical 415 (2016) 144–150
Table 3
The preparation of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4- dihydropyrano[2,3-c]pyrazoles using [cmpy]I as catalyst at 100 C.
◦
Yielda (%)
Mp. C (Lit.)
◦
Entry
Product
Time (min)
1
3
90
261–263 (264–266 [19])
2
3
4
5
4
3
3
3
94
86
92
91
226–228 (234–236 [20])
253–255 (261–263 [19])
198–200 (206–208 [15])
220–222 (250–252 [9])
6
7
3
3
83
95
229–230
216–218 (244–245 [9])
8
9
3
3
3
86
84
84
198–199 (208–210 [21])
258–259 (262–264 [19])
212–214 (208–210 [18])
1
0
1
1
4
89
242–244 (251–253 [15])

A.R. Moosavi-Zare et al. / Journal of Molecular Catalysis A: Chemical 415 (2016) 144–150
149
Table 3 (Continued)
Yielda (%)
◦
Mp. C (Lit.)
Entry
Product
Time (min)
1
1
2
3
86
219–220 (223–225 [19])
3
3
3
87
85
194–196 (210–211 [9])
242–244 (248–250 [9])
1
4
a
Isolated yield.
◦
Fig. 5. The reaction of hydrazine hydrate with ethyl acetoacetate, malononitrile and 4-chlorobenzaldehyde in the presence of reused [cmpy]I at 100 C under solvent-free
conditions.
Table 4
Comparison of the results of the condensation reaction of hydrazine hydrate with ethyl acetoacetate, malononitrile and 4-chlorobenzaldehyde catalyzed by [cmpy]I with
those obtained by the recently reported catalysts.
Reaction condition
Catalyst loading
Time (min)
20
35
45
20
3
Yielda (%)
TOFb (min−1
)
Ref.
◦
SiO2TMG, solvent-free, 100
Gamma-alumina, H2O, reflux
HDBAC, EtOH, reflux
Imidazole, H2O, 80
C
10 mol%
30 mol%
30 mol%
50 mol%
10 mol%
98
90
81
90
86
0.49
0.085
0.06
0.09
2.86
[9]
[20]
[15]
[13]
◦
C
◦
c
[cmpy]I, solvent-free, 100
C
–
a
b
c
Isolated yield.
Turn over frequency.
Our work.
To compare the efficiency of our catalyst with
the previous reported catalysts for the preparation of
were shorter, and the yields were higher when our catalyst was
utilized.
6
1
-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-
,4-dihydropyrano[2,3-c]pyrazoles, we have depicted the results
4
. Conclusions
of these catalysts to perform the reaction of hydrazine hydrate
with ethyl acetoacetate, malononitrile and 4-chlorobenzaldehyde
in Table 4. As Table 4 indicates that [cmpy]I has remarkably
improved the synthesis of pyranopyrazoles. The reaction times
In summary, we have reported the efficient synthesis
of
phenyl-1,4-dihydropyrano[2,3-c]pyrazoles in the presence of
-(carboxymethyl) pyridinium iodide {[cmpy]I} as an acetic
6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-
1

1
50
A.R. Moosavi-Zare et al. / Journal of Molecular Catalysis A: Chemical 415 (2016) 144–150
acid functionalized pyridinium salt and reusable catalyst. 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.
[11] E.S. El-Tamany, F.A. El-Shahed, B.H. Mohamed, J. Serb. Chem. Soc. 64 (1999)
–18.
12] F.M. Abdelrazek, P. Metz, N.H. Metwally, S.F. El-Mahrouky, Arch. Pharm. 339
2006) 456–460.
[13] A. Siddekha, A. Nizam, M.A. Pasha, Spectrochim. Acta Part B 81 (2011) 431.
9
[
(
[
[
[
14] K. Kanagaraj, K. Pitchumani, Tetrahedron Lett. 51 (2010) 3312–3316.
15] K. Ablajan, W. Liju, A. Tuoheti, Y. Kelimu, Lett. Org. Chem. 9 (2012) 639–643.
16] S. Muramulla, C.-G. Zhao, Tetrahedron Lett. 52 (2011) 3905–3908.
Acknowledgements
[17] T.-S. Jin, A.-Q. Wang, Z.-L. Cheng, J.-S. Zhang, T.-S. Li, Synth. Commun. 35
2005) 137–143.
(
[
[
18] S.-B. Guo, S.-X. Wang, J.-T. Li, Synth. Commun. 37 (2007) 2111–2120.
19] A.R. Moosavi-Zare, M.A. Zolfigol, E. Noroozizadeh, M. Tavasoli, V. Khakyzadeh,
A. Zare, New J. Chem. 37 (2013) 4089–4094.
The authors gratefully acknowledge the Bu-Ali Sina University,
Iran National Science Foundation (INSF) for financial support (The
Grant of Allameh Tabataba’i’s Award) to our research group and
Sayyed Jamaleddin Asadabadi University for providing support to
this work.
[20] H. Mecadon, M.R. Rohman, M. Rajbangshi, B. Myrboh, Tetrahedron Lett. 52
2011) 2523–2525.
21] M.A.E. Aleem, A.A. El-Remaily, Tetrahedron 70 (2014) 2971–2975.
(
[
[22] M.A. Zolfigol, M. Tavasoli, A.R. Moosavi-Zare, P. Moosavi, H.G. Kruger, M. Shiri,
V. Khakyzadeh, RSC Adv. 3 (2013) 25681–25685.
[
[
[
[
23] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, Org. Prep. Proced. Int. 42
2010) 95–102.
24] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, J. Iran. Chem. Soc. 7
(2010) 646–651.
25] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl.
Catal. A Gen. 400 (2011) 70–81.
26] M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, A. Zare, S.B. Azimi, Z. Asgari,
A. Hasaninejad, C. R. Chim. 15 (2012) 719–736.
Appendix A. Supplementary data
(
Supplementary data associated with this article can be found, in
the online version, at http://dx.doi.org/10.1016/j.molcata.2016.02.
003.
[
[
27] A. Zare, T. Yousofi, A.R. Moosavi-Zare, RSC Adv. 2 (2012) 7988–7991.
28] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, Z. Asgari, M. Shekouhy, A. Zare, A.
Hasaninejad, RSC Adv. 2 (2012) 8010–8013.
29] M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, G. Chehardoli, F.
Derakhshan-Panah, A. Zare, O. Khaledian, Scientia Iranica: Trans C: Chem.
Chem. Eng. 19 (2012) 1584–1590.
References
[
[
1] A.R. Moosavi-Zare, M.A. Zolfigol, O. Khaledian, V. Khakyzadeh, M.D. farahani,
M.H. Beyzavi, H.G. Kruger, Chem. Eng. J. 248 (2014) 122–127.
2] A.R. Moosavi-Zare, M.A. Zolfigol, O. Khaledian, V. Khakyzadeh, M.D. Farahani,
H.G. Kruger, New J. Chem. 38 (2014) 2342–2347.
[
[
[
[
[
30] A. Zare, F. Abi, A.R. Moosavi-Zare, M.H. Beyzavi, M.A. Zolfigol, J. Mol. Liq. 178
[
[
3] A. Khazaei, F. Abbasi, A.R. Moosavi-Zare, New J. Chem. 38 (2014) 5287–5292.
4] A. Khazaei, A.R. Moosavi-Zare, H. Afshar-Hezarkhani, V. Khakyzadeh, RSC Adv.
(
2013) 113–121.
31] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, Scientia Iranica: Trans C:
Chem. Chem. Eng. 17 (2010) 31–36.
32] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, H.G. Kruger, Z. Asgari, V.
Khakyzadeh, M. Kazem-Rostami, J. Org. Chem. 77 (2012) 3640–3645.
33] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, Z. Asgari, V. Khakyzadeh,
A. Hasaninejad, J. Ind. Engin. Chem. 19 (2013) 721–726.
4
(2014) 32142–32147.
[
[
5] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, J. Afsar, V. Khakyzadeh, O.
Khaledian, J. Chin. Chem. Soc. 62 (2015) 295––398.
6] 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.
[7] M.N. Nasr, M.M. Gineinah, Arch. Pharm. Med. Chem. 335 (2002) 289.
[8] V.K. Ahluwalia, A. Dahiya, V. Garg, Indian J. Chem. 36B (1997) 88–90.
[9] A.B. Atar, J.T. Kim, K.T. Lim, Y.T. Jeong, Synth. Commun. 44 (2014) 2679–2691.
[10] H. Junek, H. Aigner, Chem. Ber. 106 (1973) 914–921.