Nano-Zn[2-boromophenylsalicylaldiminemethylpyranopyrazole]Cl2 as a novel nanostructured Schiff base complex and catalyst for the synthesis of pyrano[2,3-d]pyrimidinedione derivatives

Article abstract of DOI:10.1002/aoc.4584

Nano-Zn[2-boromophenylsalicylaldiminemethylpyranopyrazole]Cl₂ (nano-[Zn-2BSMP]Cl₂) as a novel nanostructured Schiff base complex was prepared and characterized using several techniques. Nano-[Zn-2BSMP]Cl₂ was used as an ef

Full text of DOI:10.1002/aoc.4584

Received: 5 July 2018
DOI: 10.1002/aoc.4584
Revised: 6 August 2018
Accepted: 13 August 2018
F U L L P A P E R
Nano‐Zn[2‐boromophenylsalicylaldiminemethyl‐
pyranopyrazole]Cl as a novel nanostructured Schiff base
2
complex and catalyst for the synthesis of pyrano[2,3‐d]
pyrimidinedione derivatives
A.R. Moosavi‐Zare
| H. Goudarziafshar
| Z. Jalilian
Sayyed Jamaleddin Asadabadi University,
Asadabad 6541861841, Iran
Nano‐Zn[2‐boromophenylsalicylaldiminemethylpyranopyrazole]Cl2
(nano‐
[
Zn‐2BSMP]Cl ) as a novel nanostructured Schiff base complex was prepared
2
Correspondence
and characterized using several techniques. Nano‐[Zn‐2BSMP]Cl was used as
2
A. R. Moosavi‐Zare and Hamid
Goudarziafshar, Sayyed Jamaleddin
Asadabadi University, Asadabad,
an effective catalyst for the preparation of some pyrano[2,3‐d]pyrimidinedione
derivatives by the multicomponent reaction of malononitrile, aryl aldehydes
and barbituric acid derivatives. The novelty and efficiency of nano‐[Zn‐
6541861841, Iran.
Email: moosavizare@yahoo.com;
hamid_gafshar@yahoo.com
2BSMP]Cl as a catalyst, in comparison with some other reported catalysts, for
2
this synthetic transformation are the main features of this work.
Funding information
Sayyed Jamaleddin Asadabadi University
KEYWORDS
2
barbituric acid, multicomponent reaction, nano‐[Zn‐2BSMP]Cl , pyrano[2,3‐d]pyrimidinedione,
Schiff base complex
1
| INTRODUCTION
Multicomponent reactions have a significant role in the
preparation of target compounds by the reaction of three
or more compounds to afford a single product.
[
22–31]
The preparation of pyrano[2,3‐d]pyrimidinedione deriva-
tives is significant due to their important antitumour,
antibacterial,
and antiallergic properties. Additionally, some of them
can be used as antimalarial, antifungal, analgesic
and antibiotic compounds. Various procedures have
been introduced for the synthesis of pyrano[2,3‐d]
pyrimidinedione derivatives in the presence of
catalysts such as Zn[L‐proline] ,
dibutylamine,
KAl(SO ) ⋅12H O,
Urea‐SO H, [DABCO](HSO ) (HSO ) , sulfonic acid
[
1]
Schiff bases are prepared by the reaction of a primary
amine with an aldehyde or a ketone. Schiff base
compounds are widely studied and applied as one of the
significant classes of ligands due to the easy and conve-
nient protocols for their preparation and their interesting
[2]
[3]
[4]
antihypertensive,
bronchiodilator
[5]
[6]
[7]
[8]
[9]
[
32]
coordination chemistry.
A Schiff base ligand as an
imine or azomethine compound can be used to produce
a Schiff base complex by metal–ligand coordination.
These compounds have been shown to exhibit antibacte-
rial, antifungal, anticancer, antioxidant, anti‐inflamma-
tory, antimalarial and antiviral properties. Also, they
[10]
[11]
ZnO nanopowders,
2
[
12]
[13]
potassium fluoride,
L‐proline,
[
14]
[15]
Fe O @SiO @(CH ) ‐
4
2
2
3
4
2
2 3
[
16]
[17]
3
3 2
[19]
4 2
[
18]
[20]
nanoporous silica,
DABCO,
triethylamine,
boric
have been introduced as catalysts for the preparation of
[
21]
[33–35]
acid and nanotitania sulfuric acid. It is noteworthy that
some of them have some disadvantages including harsh
reaction conditions, low yields and long reaction times.
Pyrano[2,3‐d]pyrimidinediones can be prepared by
the one‐pot multicomponent synthesis of barbituric acid
derivatives, various aldehydes and malononitrile.
various organic compounds.
Recently, we have
reported a new category of Schiff base obtained by the
reaction
of
pyranopyrazole
derivatives
with
[
36–39]
salicylaldehyde and various metal salts.
In the work
reported herein, in continuation of our previous investi-
gations, we prepared and characterized nano‐Zn[2‐
Appl Organometal Chem. 2018;e4584.
wileyonlinelibrary.com/journal/aoc
© 2018 John Wiley & Sons, Ltd.
1 of 11
https://doi.org/10.1002/aoc.4584

2
of 11
MOOSAVI‐ZARE ET AL.
boromophenylsalicylaldiminemethylpyranopyrazole]Cl2
nano‐[Zn‐2BSMP]Cl ; Figure 1) and used it as an effec-
tive catalyst for the preparation of pyrano[2,3‐d]
flask containing salicylaldehyde (1.5 mmol), connected to
a reflux condenser and stirred at 120 °C for 72 h. After this
time, the reaction mixture was washed three times with
ethyl acetate and hexane (9/1) to purify nano‐[Zn‐
(
2
pyrimidinediones (Scheme 1).
2
BSMP]Cl from excess salicylaldehyde.
2
2
2
| EXPERIMENTAL
.1 | General
2
.3 | General Procedure for Synthesis of
Pyrano[2,3‐d]pyrimidinediones using
Nano‐[Zn‐2BSMP]Cl
All chemicals were purchased from Merck or Fluka. 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 silica gel SIL G/UV 254 plates.
2
A mixture of barbituric acid derivative (2 mmol),
aldehyde (2 mmol), malononitrile (2.2 mmol), nano‐
[Zn‐2BSMP]Cl2 (8 mol%) and 10 ml of EtOH–H O
2
(
19:1) was added to a 25 ml round‐bottomed flask con-
nected to a reflux condenser and stirred in an oil‐bath
at 40°C. After completion of the reaction, as monitored
by TLC, the reaction mixture was extracted with warm
ethanol (10 ml) to separate from the catalyst. Then, the
crude product was purified by recrystallization from a
mixture of ethanol and water (9:1) to afford the desired
product.
2
2
.2 | Procedure for Synthesis of Nano‐[Zn‐
BSMP]Cl
2
A mixture of 2‐bromobenzaldehyde (0.183 g, 1 mmol),
malononitrile (0.066 g, 1 mmol), ethyl acetoacetate
(0.13 g, 1 mmol), hydrazine hydrate (1.25 mmol) and
isonicotinic acid (0.1 mmol, 0.0123 g, 10 mol%) was added
in a 25 ml round‐bottomed flask connected to a reflux
condenser, and stirred at 100°C. After the completion of
the reaction, as monitored by TLC, the reaction mixture
was cooled to room temperature. Water was added to the
reaction mixture to dissolve isonicotinic acid and the aque-
ous layer was separated from the reaction mixture. Then,
the solid residue (crude product) was triturated by a
mixture of ethanol and water (19/1) to 6‐amino‐4‐(2‐
bromophenyl)‐3‐methyl‐2,4‐dihydropyrano[2,3‐c]pyrazole‐
3
| RESULTS AND DISCUSSION
Nano‐[Zn‐2BSMP]Cl2 was synthesized by the reaction
of 2‐bromobenzaldehyde with ethyl acetoacetate,
malononitrile and hydrazine hydrate to give the related
[37]
5‐carbonitrile as an amine product. The prepared amine
(
1 mmol) and ZnCl (1 mmol) were pulverized in a mortar
2
for 10 min and then transferred to a 25 ml round‐bottomed
FIGURE 1 Proposed structures of nano‐[Zn‐2BSMP]Cl
2
SCHEME 2 Preparation of nano‐[Zn‐2BSMP]Cl
2
SCHEME 1 Preparation of pyrano[2,3‐
d]pyrimidine dione derivatives catalysed
by nano‐[Zn‐2BSMP]Cl
2

MOOSAVI‐ZARE ET AL.
3 of 11
FIGURE 2 IR spectrum of nano‐[Zn‐2BSMP]Cl
2
[
40]
pyranopyrazole according to previous literature,
which
was then reacted with salicylaldehyde and ZnCl to afford
2
nano‐[Zn‐2BSMP]Cl2 as a nano‐Schiff base complex
(
Scheme 2). The structure of nano‐[Zn‐2BSMP]Cl was
2
identified using infrared (IR) spectroscopy, scanning
electron microscopy (SEM), energy‐dispersive X‐ray
(
EDX) analysis, thermogravimetric analysis (TGA),
differential thermogravimetry (DTG), UV spectroscopy
and mass analysis.
The IR spectrum of the catalyst displayed a broad
−
1
peak at 3000–3600 cm which could be assigned to
O―H stretching of OH group and the peak observed at
−
1
1
654 cm could be assigned to stretching mode of C¼N
bond in the structure of the Schiff base complex coordi-
nated with zinc chloride (Figure 2).
FIGURE 3 SEM micrograph of nano‐[Zn‐2BSMP]Cl
2
FIGURE 4 EDX analysis of nano‐[Zn‐2BSMP]Cl
2

4
of 11
MOOSAVI‐ZARE ET AL.
2
FIGURE 5 TGA curve of nano‐[Zn‐2BSMP]Cl at 0–800°C, with a temperature increase rate of 10°C
2
FIGURE 6 DTG analysis of nano‐[Zn‐2BSMP]Cl at of 0–800°C, with a temperature increase rate of 10°C

MOOSAVI‐ZARE ET AL.
5 of 11
temperatures above 300°C (Figures 5 and 6). A small
weight loss before 300°C could be related to removal of
the solvents that remained in the complex or water
coordinated with the complex.
UV spectral analysis of the particles in the structure
of complex gave further evidence of the formation of
nano‐[Zn‐2BSMP]Cl . UV spectra were recorded in
2
dimethylsulfoxide (DMSO) as solvent. The maximum of
absorption for amine, 2BSMP (Schiff base), nano‐[Zn‐
2
BSMP]Cl and ZnCl appeared at 261, 292, 257 and
2 2
256 nm, respectively (Figure 7). Therefore, λmax of the
complex is different from that of some other species used
in the preparation of nano‐[Zn‐2BSMP]Cl2.
After the preparation and identification of the
catalyst, to optimize the reaction conditions, the
reaction of barbituric acid, 4‐chlorobenzaldehyde and
malononitrile was used as a model reaction. The model
reaction was conducted in the presence of various
FIGURE 7 UV spectra of amine, Schiff base (2BSMP), nano‐[Zn‐
2
2 2
BSMP]Cl and ZnCl in DMSO
SEM micrographs of nano‐[Zn‐2BSMP]Cl were also
amounts of nano‐[Zn‐2BSMP]Cl in the range 25–60°C
2
2
studied, showing that the particles were less than
in ethanol and water (19:1). The best result was
obtained using 8 mol% of nano‐[Zn‐2BSMP]Cl2 at
40°C. Increasing the reaction time did not improve the
results (Table 1). The model reaction was also
conducted using various solvents in comparison with
ethanol and water (19:1) which did not make a marked
improvement. The solvent‐free condition was also
studied, which was not much favourable in comparison
with the use of solvent (Table 1, entry 8). The model
reaction was also carried out in the presence of
1
00 nm in size (Figure 3).
EDX analysis of nano‐[Zn‐2BSMP]Cl was conducted,
2
indicating the presence of the desired elements, namely
carbon, oxygen, nitrogen, bromine, zinc and chlorine, in
the structure of the catalyst. Therefore, the structure of
nano‐[Zn‐2BSMP]Cl2 was completely confirmed via
EDX analysis (Figure 4).
In order to investigate the thermal stability of the
catalyst, TGA and DTG of nano‐[Zn‐2BSMP]Cl2 were
conducted, which showed that it could not be used at
8 mol% of ZnCl in ethanol and water (19:1) at 40°C
2
TABLE 1 Effect of amount of catalyst, type of solvents and temperature on the reaction of barbituric acid, 4‐chlorobenzaldehyde and
malononitrile
a
Entry
Catalyst (mol%)
Solvent
Temperature (°C)
Time (min)
Yield (%)
b
1
2
3
4
5
6
7
8
9
—
3
Ethanol–water
Ethanol–water
Ethanol–water
Ethanol–water
Ethanol–water
Ethanol–water
Ethanol–water
—
40
40
40
40
40
25
60
40
40
40
40
40
40
120
15
10
4
20
80
6
95
8
97
10
8
4
97
20
4
60
8
95
8
10
8
Trace
90
8
2
H O
10
11
12
13
8
CH
3
CN
20
25
40
25
50
8
Ethyl acetate
Acetone
45
8
25
8
THF–H
2
O
30
a
Isolated yield.
b
Ratio of ethanol to water is 19 to 1.

6
of 11
MOOSAVI‐ZARE ET AL.
TABLE 2 Synthesis of pyrano[2,3‐d]pyrimidinediones using nano‐[Zn‐2BSMP]Cl
2
a
Entry
Product
Time (min)
Yield (%)
M.p. (Lit.) (°C)
[
8]
1
8
95
273–275 (279–280)
2
3
5
92
96
230–232
246–248
10
[
7]
4
12
96
213–215 (212)
[
21]
5
6
9
6
90
97
210–212 (209–211)
239–240
[
9]
7
11
92
256–259 (268–270)
[
12]
8
9
13
75
93
160–162 (169–171)
238–240 (240–242)
[
21]
8
(Continues)

MOOSAVI‐ZARE ET AL.
7 of 11
TABLE 2 (Continued)
a
Entry
Product
Time (min)
Yield (%)
M.p. (Lit.) (°C)
[
21]
1
0
7
92
213–215 (211–214)
[
41]
1
1
6
5
95
97
237–238 (239–240)
251–253 (254–256)
[
[
[
14]
12]
12]
1
1
1
2
3
4
3
9
95
95
227–230 (228–232)
233–235 (235–236)
[
21]
1
1
5
6
10
13
90
85
232–235 (237–238)
200–207 (200–202)
[
9]
[
21]
1
7
13
25
225–227 (226)
(Continues)
to compare with nano‐[Zn‐2BSMP]Cl . In this reaction
aldehydes to give
a
series of pyrano[2,3‐d]
2
the desired product was obtained in 58% yield after 2 h.
To study the generality and scope of the catalyst, we
continued our study using nano‐[Zn‐2BSMP]Cl2
pyrimidinedione derivatives at 40°C. Various aromatic
aldehydes containing electron‐withdrawing substituents,
electron‐releasing substituents and halogens on their
aromatic rings were utilized successfully in this reaction,
(
8 mol%) in EtOH–H O (19:1) with various aromatic
2

8
of 11
MOOSAVI‐ZARE ET AL.
TABLE 2 (Continued)
a
Entry
18
Product
Time (min)
Yield (%)
M.p. (Lit.) (°C)
7
97
228
[
21]
1
9
5
97
234–235 (235–237)
[
42]
2
2
0
1
9
7
88
85
220–222 (211–212)
240–245 (246–247)
[
42]
[
42]
2
2
2
3
17
80
90
247–248 (238–239)
256–258 (243–244)
[
42]
9
[
16]
2
4
5
85
247–248 (235–237)
a
Isolated yield.
and gave the corresponded products in high yields and in
short reaction times (Table 2).
In a plausible mechanism, which is shown in
Scheme 3, firstly, malononitrile reacts with carbonyl
group of aldehyde which is activated by nano‐[Zn‐
compound I as Michael acceptor to afford II. Finally,
cyclocondensation of II gives III which is converted to
the desired product.
The reusability of nano‐[Zn‐2BSMP]Cl2 was also
investigated in the reaction of barbituric acid (1 mmol),
4‐chlorobenzaldehyde (1 mmol) and malononitrile
(1 mmol). After completion of the reaction, as monitored
by TLC, the reaction mixture extracted with warm
2
BSMP]Cl2 and affords intermediate I after removing
one molecule of H O. Barbituric acid converts to enol
2
form after tautomerization and attacks cyanoolefin

MOOSAVI‐ZARE ET AL.
9 of 11
SCHEME 3 Proposed mechanism for
synthesis of pyrano[2,3‐d]
pyrimidinediones catalysed by nano‐[Zn‐
2
BSMP]Cl
2
ethanol and water (19:1) and separated from the catalyst
after filtration. The catalyst was dried and reused for
another reaction. We observed that the catalytic activity
of the catalyst was retained for four successive runs
within the limits of experimental error (Figure 8).
2
TABLE 3 Comparison of efficiency of nano‐[Zn‐2BSMP]Cl with
that of various reported catalysts for the model reaction
Catalyst Time Yield
Condition
amount
(min) (%)
Ref.
To show the merit of this method, a comparison of the
present work with a few previously reported methods for
[
[
[
11]
14]
16]
ZnO nanopowders/
solvent‐free, 90°C
25 mol%
150
86
93
97
KAl(SO
4
)
2
⋅12H
2
O/
10 mol%
0.01 g
40
H
2
O, 80°C
Fe
3
O
4
@SiO @(CH
Urea‐SO H/HCl/
solvent‐free, 60°C
DABCO](HSO (HSO
O, reflux
2
2
)
3
‐
30
3
[
[
17]
18]
[
3
)
2
4
)
2
/ 0.01 g
7
90
30
H
2
SBA‐Pr‐SO3H/solvent‐
free, 140°C
0.02 g
0.02 g
45
[
[
21]
21]
TSA/EtOH–H
B(OH) /THF–H
Nano‐[Zn‐2BSMP]Cl
EtOH–H O, 40°C
2
O, reflux
60
110
10
89
85
96
3
2
O, reflux 10 mol%
8 mol%
2
/
This
work
FIGURE 8 Reaction of barbituric acid, 4‐chlorobenzaldehyde
2
and malononitrile in the presence of reused nano‐[Zn‐2BSMP]Cl
2

10 of 11
MOOSAVI‐ZARE ET AL.
the formation of pyrido[2,3‐d:6,5‐d′]pyrimidine is
presented in Table 3. The results showed that this method
is comparable to some previously reported methods in
terms of reaction times, temperatures and yields
[10] M. M. Heravi, A. Ghods, K. Bakhtiari, F. Derikv, Synth.
Commun. 2010, 40, 1927.
[11] N. Maleki, Z. Shakarami, S. Jamshidian, M. Nazar, Acta Chem.
IASI 2016, 24, 20.
(Table 3).
[12] A. R. Bhat, A. H. Shalla, R. S. Dongre, J. Taibah Univ. Sci. 2016,
10, 9.
[
[
[
[
[
[
[
[
[
[
[
13] M. N. Elinson, F. V. Ryzhkov, V. M. Merkulova, A. I. Ilovaisky,
4
| CONCLUSIONS
G. I. Nikishin, Heterocycl. Commun. 2014, 20, 281.
14] A. Mobinikhaledi, N. Foroughifar, M. A. Bodaghi Fard, Synth.
React. Inorg. Met.‐Org. Nano‐Met. Chem. 2010, 40, 179.
In summary, we have prepared nano‐[Zn‐2BSMP]Cl as
2
a novel nanostructured Schiff base complex, which was
characterized using several techniques including IR
spectroscopy, SEM, EDX analysis, TGA, DTG, UV
spectroscopy and mass analysis. Nano‐[Zn‐2BSMP]Cl2
was used as an efficient catalyst for the one‐pot multi-
component synthesis of pyrano[2,3‐d]pyrimidinedione
derivatives by the reaction of malononitrile, aryl
aldehydes and barbituric acid derivatives. The novelty
15] M. Bararjanian, S. Balalaie, B. Movassagh, A. M. Amani,
J. Iran. Chem. Soc. 2009, 6, 436.
16] M. A. Zolfigol, R. Ayazi‐Nasrabadi, S. Baghery, Appl.
Organometal. Chem. 2016, 30, 273.
17] N. Seyyedi, F. Shirini, M. S. N. Langarudi, RSC Adv. 2016, 6,
44630.
18] G. M. Ziarani, S. Faramarzi, S. Asadi, A. Badiei, R. Bazl, M.
Amanlou, DARU J. Pharm. Sci 2013, 21.
and efficiency of nano‐[Zn‐2BSMP]Cl as a catalyst, in
2
19] S. Jain, P. K. Paliwal, G. N. Babu, A. Bhatewara, J. Saudi Chem.
Soc. 2014, 18, 535.
comparison with some other reported catalysts for this
synthetic transformation, are the main features of this
work.
20] D. Azarifar, R. Nejat‐Yami, F. Sameri, Lett. Org. Chem. 2012, 9,
435.
21] A. Khazaei, H. A. A. Nik, A. R. Moosavi‐Zare, J. Chin. Chem.
Soc. 2015, 62, 675.
ACKNOWLEDGEMENTS
22] J. Zhu, H. Bienayme (Eds), Multicomponent Reactions, Wiley,
Weinheim 2005.
The authors gratefully acknowledge Sayyed Jamaleddin
Asadabadi University for providing support to this work.
23] A. Khazaei, M. A. Zolfigol, A. R. Moosavi‐Zare, F. Abi, A. Zare,
H. Kaveh, V. Khakyzadeh, M. Kazem‐Rostami, A. Parhami, H.
Torabi‐Monfared, Tetrahedron 2013, 69, 212.
ORCID
[
24] M. A. Zolfigol, A. Khazaei, A. R. Moosavi‐Zare, A. Zare, Z.
A.R. Moosavi‐Zare http://orcid.org/0000-0003-0321-9326
H. Goudarziafshar http://orcid.org/0000-0002-5930-6253
Asgari, V. Khakyzadeh, A. Hasaninejad, J. Ind. Eng. Chem.
2013, 19, 721.
[
[
[
[
[
25] A. R. Moosavi‐Zare, M. A. Zolfigol, S. Farahmand, A. Zare, A.
R. Pourali, R. Ayazi‐Nasrabadi, Synlett 2014, 25, 193.
REFERENCES
26] M. A. Zolfigol, A. Khazaei, A. R. Moosavi‐Zare, A. Zare, V.
Khakyzadeh, Appl. Catal. A 2011, 400, 70.
[
1] a) E. M. Griva, S. Lee, C. W. Siyal, D. S. Duch, C. A. Nichol,
J. Med. Chem. 1980, 23, 327. b) G. L. Anderson, J. L. Shim, A.
D. Broom, J. Org. Chem. 1976, 41, 1095.
27] A. R. Moosavi‐Zare, M. A. Zolfigol, M. Daraei, Synlett 2014, 25,
1
173.
28] A. R. Moosavi‐Zare, M. A. Zolfigol, Z. Rezanejad, Can. J. Chem.
016, 94, 626.
[
2] M. M. Ghorab, A. A. Y. Hassan, Phosphorus Sulfur Silicon
Relat. Elem. 1998, 141, 251.
2
[
3] D. Heber, C. Heers, U. Ravens, Pharmazie 1993, 48, 537.
4] W. J. Coates, Eur. Pat., 351058, 1990; Chem. Abstr. 1990, 113,
29] A. R. Moosavi‐Zare, M. A. Zolfigol, R. Salehi‐Moratab, E.
Noroozizadeh, J. Mol. Catal. A 2016, 415, 144.
[
4
0711.
5] N. Kitamura, A. Onishi, Eur. Pat., 163599, 1984; Chem. Abstr.
984, 104, 186439.
[30] A. R. Moosavi‐Zare, M. A. Zolfigol, R. Salehi‐Moratab, E.
Noroozizadeh, Can. J. Chem. 2017, 95, 194.
[
[
[
[
[
31] A. Khazaei, A. R. Moosavi‐Zare, F. Gholami, V. Khakyzadeh,
1
Appl. Organometal. Chem. 2016, 30, 691.
[
6] J. Davoll, J. Clarke, E. F. Eislager, J. Med. Chem. 1972, 15, 837.
32] B. Sreenivasulu, Schiff Base and Reduced Schiff Base Ligands,
John Wiley & Sons Ltd 2012.
[
7] I. Devi, B. Kumar, P. J. Bhuyan, Tetrahedron Lett. 2003, 44,
8
307.
8] T. S. Jin, L. B. Liu, Y. Zhao, T. S. Li, J. Chem. Res. 2005, 2005,
62.
9] J. Albadi, A. Mansournezhad, T. Sadeghi, Res. Chem. Intermed.
015, 41, 8317.
33] E. Yousif, A. Majeed, K. Al‐Sammarrae, N. Salih, J. Salimon, B.
Abdullah, Arab. J. Chem. 2017, 10, S1639.
[
[
1
34] A. M. Abu‐Dief, I. M. A. Mohamed, Beni‐Suef Univ. J. Basic
Appl. Sci. 2015, 4, 119.
2
[35] M. Rezaeivala, H. Keypour, Coord. Chem. Rev. 2014, 280, 203.

MOOSAVI‐ZARE ET AL.
11 of 11
[
[
[
[
[
[
[
36] A. R. Moosavi‐Zare, H. Goudarziafshar, S. Dastbaz, J. Chin.
SUPPORTING INFORMATION
Chem. Soc. 2017, 64, 727.
Additional supporting information may be found online
in the Supporting Information section at the end of the
article.
37] H. Goudarziafshar, A. R. Moosavi‐Zare, K. Saki, M.
Abdolmaleki, J. Chin. Chem. Soc. 2017, 64, 1496.
38] A. R. Moosavi‐Zare, H. Goudarziafshar, L. Ghaffari, Appl.
Organometal. Chem. 2017, 31, e3845.
How to cite this article: Moosavi‐Zare AR,
Goudarziafshar H, Jalilian Z. Nano‐Zn[2‐
boromophenylsalicylaldiminemethyl‐
39] A. R. Moosavi‐Zare, H. Goudarziafshar, K. Saki, Appl.
Organometal. Chem. 2018, 32, e3968.
40] M. A. Zolfigol, M. Tavasoli, A. R. Moosavi‐Zare, P. Moosavi, H.
G. Kruger, M. Shiri, V. Khakyzadeh, RSC Adv. 2013, 3, 25681.
pyranopyrazole]Cl as a novel nanostructured Schiff
2
base complex and catalyst for the synthesis of
pyrano[2,3‐d]pyrimidinedione derivatives. Appl
Organometal Chem. 2018;e4584. https://doi.org/
41] A. Mobinikhaledi, M. A. Bodaghi Fard, Acta Chim. Slov. 2010,
5
7, 931.
10.1002/aoc.4584
42] K. A. Kumar, P. Jayaroopa, Int. J. PharmTech Res. 2013, 5, 1473.