Ag/Tio2 nano thin films catalyzed efficient synthesis of 6-amino-4-aryl-3-methyl-1,4-dihydropyrano[2,3-C] pyrazole-5-carbonitriles at green conditions

Article abstract of DOI:10.13005/ojc/330229

Ag/TiO₂ nano thin films was found to be efficient and green heterogeneous catalyst for the synthesis of dihydropyrano[2,3-c]pyrazole derivatives via a one-pot three-component reaction between 3-methyl-1H-pyrazol-5(4H)-one or 3-methyl-1(phenyl)-

Full text of DOI:10.13005/ojc/330229

ISSN: 0970-020 X
CODEN: OJCHEG
017, Vol. 33, No. (2):
Pg. 814-820
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Free Access, Peer Reviewed Research Journal
2
www.orientjchem.org
Ag/Tio Nano Thin Films Catalyzed Efficient Synthesis of
2
6-Amino-4-Aryl-3-Methyl-1,4-Dihydropyrano[2,3-C]
Pyrazole-5-Carbonitriles At Green Conditions
1
1,
2
SHARMIN IRANI, MALEk TAHER MAGHSOODLOU, * M. SAEED HADAvI,
1
3
NOURALLAH HAꢀERI, and MOJTAꢁA LASHkARI
1
Department of Chemistry, Faculty of Sciences, University of Sistan and
Baluchestan, P. O. Box 98135-674, Zahedan, Iran.
Department of Physics, Faculty of Sciences, University of Sistan and
2
Baluchestan, P. O. Box 98135-674, Zahedan, Iran.
Faculty of Science, Velayat University, Iranshahr, Iran.
3
*
Corresponding auhtor E-mail: mt_maghsoodlou@chem.usb.ac.ir
http://dx.doi.org/10.13005/ojc/330229
(Received: February 25, 2017; Accepted: March 22, 2017)
AꢁSTRACT
Ag/TiO nano thin films was found to be efficient and green heterogeneous catalyst for the
2
synthesis of dihydropyrano[2,3-c]pyrazole derivatives via a one-pot three-component reaction between
3-methyl-1H-pyrazol-5(4H)-one or 3-methyl-1(phenyl)-pyrazol-5(4H)-one, aldehydes and malononitrile
at room temperature.Ag/TiO andTiO films were prepared by spray pyrolysis technique and the effect
2
2
of substrate temperature and silver incorporation on optical, morphological and structural properties
were investigated by XRD, AFM, spectrophotometry and photoluminescent spectroscopy.The results
of this study shows adding of Ag to TiO films increased the optical absorption due to plasmonic
2
behavior of Ag free electrons. XRD analysis was revealed the Hexagonal structure with Anatase
phase and 101 prefer crystal orientation which is prefer phase for photocatalyst applications.
keywords: Ag/TiO nano thin films, dihydropyrano[2,3-c]pyrazole, 3-methyl-1H-pyrazol-5(4H)-one,
2
3-methyl-1(phenyl)-pyrazol-5(4H)-one, aldehydes, malononitrile
INTRODUCTION
photo catalysis has been studied extensively due
to many industrial applications. Unfortunately, this
semiconductor has limited catalytic efficiency due
to its wide energy band gap; it is just sensitive to
UV radiation. The energy band gap of bulk TiO2
is 3 eV and 3.2 eV for rutile and anatase phases,
Titanium dioxide is the most popular
and efficient semiconductor photo catalyzer due
to its strong oxidative ability of photo generated
1
-2
electron-hole pairs on its surface . This efficient

815
IRANI et al., Orient. J. Chem., Vol. 33(2), 814-820 (2017)
20
respectively. TiO as a photo catalysis have been effects .Furthermore, some pyrazoles are employed
2
widely studied in anatase and rutile phases.Its photo in polymer and supramolecular chemistry, in the
catalytic activity in anatase phase is more than other food industry, and as UV stabilizers and cosmetic
3
phases .
colorings and in some cases it was observed
that these compounds also have liquid crystal
21-25
In recent years nano-composite thin films, properties
. Dihydropyrano[2,3-c]pyrazoles, are
due to their industrial application, have been studied one of the most important pyrazole compounds
4
-7
by many researchers . Ag/TiO nano particles and they have received considerable attention
2
have been widely used in photo electrochemical owing to their biological activity and they have
and photo catalyst applications. One of the most been utilize as a template for medicinal chemistry.
important problems which decrease the photocatalyst They exhibited many biological activities like
26
27
efficiency is electron-hole recombination. It is well antimicrobial , insecticidal , and anti-inflammatory
2
8
experienced that noble metal doping reduces
. Moreover, dihydropyrano[2,3-c]pyrazoles exhibit
29
the electron-hole recombination rate and hence molluscicidal activity , and has been identified as
increases the photocatalytic efficiency. In this a screening kit for Chk1 kinase inhibitor . Because
30
work, Ag/TiO nanocomposite films was deposited of the importance of these compounds, a number
2
on microscope glass slides and also insides of of methods have been reported for their synthesis
beakers by spray pyrolysis technique and the effect in the presence of various catalysts such as ionic
3
1,32
33-36
37
of silver incorporation on optical, crystal structure, liquids
surface morphology and recombination rate were
characterized and reported.
, organic bases
, amberlyst , glycine
38
39
40
, per-6-amino-b-cyclodextrin , and iodine
.
In recent years, we investigated the
Combinatorial methods employing synthesis of these compounds in the presence
multicomponent reactions have recently become of diverse green catalysts such as trichloroacetic
4
1-45
the focus of considerable interest because of their acid, cellulose, L-proline and in green media.
swift and convenience of synthesis of various classes In continuation of our research on multi-component
8, 9
46-49
of compounds. Multicomponent reactions (MCRs), reactions,
herein we would like to describe
defined as one-pot reactions in which at least three the synthesis of dihydropyrano[2,3-c]pyrazole
functional groups are joined via covalent bonds, derivatives, our attention was drawn to the of Ag/TiO2
gradually gain importance in synthetic organic nano thin films as an effective and highly reusable
8
-11
chemistry
.
catalyst and the synthesis of dihydropyrano[2,3-c]
pyrazole was investigated in the presence of this
Nitrogen-containing heterocycles, key catalyst.
element and widespread structural motif in many
drugs, are important design feature of medicinal
RESULTS AND DISCUSSIONS
1
2
agents in medicinal chemistry . Moreover, they
can act as biomimetic and active pharmacophores
In the opinion of experiment of this
1
3
.
Pyrazoles are among the most commonly new process at first we examined the reaction of
investigatedorganicnitrogen-containingheterocycles aldehydes 1, malononitrile 2 and 3-methyl-1H-
compounds with 5-membered ring. Pyrazoles have pyrazol-5(4H)-one or 3-methyl-1(phenyl)-pyrazol-
many applications in the field of pharmaceutical 5(4H)-one 3 in EtOH at room temperature in the
industry, and medical chemistry due to their proximity of Ag/TiO nano thin films to get the
2
1
4
biological activities such as antifungal , antiviral forecasted dihydropyrano[2,3-c]pyrazole derivatives.
1
5
16
17
,
anticancer , and anti-inflammatory properties
.
differents temperature and solvent were tested to
Due to these properties, they are widely utilized in optimize the reaction position. The results exhibited
the pharmaceutical industry, medicinal chemistry and that the reaction proceeds with good yields when
18, 19
they are also important core in natural products
.
EtOH was used at room temperature.Try again, when
In addition pyrazoles have been used for treatment of we examined the reaction in absence of catalyst,
type 2 diabetes, obesity, thrombopiotinmimetics and no significant change in the reaction mixture after
antiangiogenesis because of their kinase inhibitory 48 hours has been seen which showed the catalyst

IRANI et al., Orient. J. Chem., Vol. 33(2), 814-820 (2017)
816
has good effect on reaction yields. With the optimal
conditions in hand, we found the scope of the reaction
for the construction of various dihydropyrano[2,3-c]
pyrazoles.
Micheal addition reaction between intermediate
A and B lead to intermediate C. Intramolecular
cyclization of intermediate C by attack of hydroxyl
group to nitrile group in the presence of titanium
oxide lead to intermediate E. Finally, imine-enamine
tautomerization of E gives desirable product 4.
Finally, we increased the reaction with
variousaldehydesincludingbothelectronwithdrawing
and electron-donating substituents. The reactions
are generally clean, and desired products 4a-r was
obtained in good yields.The results are summarized
in Table 1.
We also investigated the recycling of the
Ag/TiO nano thin films as the catalyst using the
2
model reaction of 3-methyl-1(phenyl)-pyrazol-5(4H)-
one, malononitrile and 4-methoxybenzaldehyde.
When the reaction is done, the crude product was
purified by ltration and washed with EtOH (3 × 2
mL) to give the desired products. Then, the vial Ag/
According to our results, we can propose
the reaction mechanism shown in Scheme 2.Initially,
Knoevenagel condensation reaction between
aldehyde and malononitrile in the presence of
catalyst lead to the formation of alkene A.Thereafter,
TiO nano thin films washed with EtOH and checking
2
the reusability under similar reaction conditions.
The results showed that Ag/TiO nano thin films is
2
Ar
Me
Me
O
CN
Ag/TiO nano thin films
2
N
Ar
H
+
NC
CN
+
N
O
N
R
N
O
NH2
EtOH, r.t
1
2
R
3
4
Scheme 1: Synthesis of dihydropyrano[2,3-c]pyrazole deriꢂatiꢂes 4a-r
Table 1: Synthesis of dihydropyrano[2,3-c]pyrazole deriꢂatiꢂes 4a-r
Entry
Ar
R
Product
Time
yield (%)a
O.b. m.p
Lit. m.p
[ C]
“
“
(min)
( C)
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
C H5
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
H
4a
4b
4c
4d
4e
4f
4g
4h
4i
4j
4k
4l
4m
4n
4o
4p
4q
4r
60
40
18
20
35
20
35
25
20
30
22
25
20
70
40
45
40
20
85
85
97
90
70
90
80
85
80
85
95
80
85
70
85
85
75
80
166-168
213-215
170-171
181-183
220-221
235-237
211-213
209-211
157-159
194-195
197-199
192-194
197-199
166-168
176-177
142-144
223-225
174-176
168-170 [43]
213-215[43]
169-171[43]
181-183 [45]
219-221[45]
235-237 [43]
210-212 [43]
210-212[43]
158-160 [45]
190-192 [43]
195-197 [43]
193-194 [45]
198-200 [45]
169-170 [43]
174-175 [44]
143-145 [45]
224-226 [43]
175-177 [45]
6
4-Br-C H4
6
4-NO -C H
2
6
4
2-Cl-C H4
6
4-OH -C H4
6
2,4-Cl C H
2
6
3
4-OMe-C H4
6
2,5-(CH O) C H
3
2
6
3
3-OEt,4-OHC H3
6
0
1
2
3
4
5
6
7
8
4-Cl-C H4
6
3-NO -C H
2
6
4
biphenyl-4-yl
naphthyl 2- carbaldehyd
C H5
6
4-OMe-C H4
H
H
H
H
6
2-Cl-C H4
6
4-OH -C H4
6
4-Br-C H4
6
a
Yields refer to the isolated pure products.

817
IRANI et al., Orient. J. Chem., Vol. 33(2), 814-820 (2017)
a stable catalyst in reaction media and reused four (Table 2). As it is shown in Table2, Ag/TiO nano
2
times without significant loss of its catalytic activity thin films remarkably improved the synthesis of 1,4-
(
Fig. 1). Catalyst could be recovered because all dihydropyrano[2,3-c]- pyrazole in different terms, for
eighteen derivatives of dihydropyrano[2,3-c]pyrazole example in terms of reaction conditions.
were synthesis from only one Ag/TiO nano thin
2
films.
Experimental
AllreagentswerepurchasedfromMerckand
To show the value of the present procedure Sigma-Aldrich and used without further purification.
in comparison with reported results in the other All yields refer to isolated products after purification.
documents, we compared result of Ag/TiO nano Products were characterized by comparison physical
2
thin films with reported catalysts in the synthesis of data with authentic samples and spectroscopic data
derivatives of dihydropyrano[2,3-c]pyrazole, such (IR and NMR). The NMR spectra were recorded
50
as g-alumina , TEAA (triethylammonium acetate) on a Bruker Avance DRX 300 MHz instrument. IR
5
1
52
53
,
,
trichloroacetic acid , imidazole , ceric sulfate spectra were recorded on a JASCO FT-IR 460 plus
5
2
54
ultrasound irradiation , nanosized magnesium spectrophotometer and Avance, respectively.
5
5
56
57
58
oxide , L-proline , H PO /Al O , cellulose
3
4
2
3
O
Ag/TiO
2
nano thin films
H
CN
CN
Ar
H
+
NC
CN
Ar
Knoevenagel
condensation
1
2
A
N
N
O
OH
N
N
R
R
3
B
Ag/TiO2 nano
thin films
Ar
CN
CN
Ar
CN
CN
2
Ag/TiO nano
thin films
H
CN
CN
+
N
N
N
N
OH
O
OH
N
Tautomerization
N
Ar
R
R
C
R
A
B
D
Ar
Ar
imine-enamine
tautomerization
CN
NH
CN
D
N
N
N
N
O
O
NH2
R
R
4
E
Scheme 2: Proposed mechanism for the synthesis of dihydropyrano[2,3-c]pyrazole
General procedure for the synthesis of 3-methyl-
1
,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
derivatives
To a magnetic stirred solution of aromatic
aldehydes 1 (1.0 mmol), malononitrile 2 (1.0 mmol)
and 3-methylpyrazol-5(4H)-one 3 (1.0 mmol) in
EtOH (2 mL) Ag/TiO nano thin films was added at
2
room temperature.The progress of the reaction was
monitored by TLC. After completion of the reaction,
the crude solid product was filtered for separation
of product and washed with EtOH (3×2 mL) to give
the pure product. All of the products are known.
Fig. 1:The recycling of the Ag/TiO nano thin
2
films as catalyst

IRANI et al., Orient. J. Chem., Vol. 33(2), 814-820 (2017)
818
Table 2: Comparison the result of Ag/TiO nano thin films with other catalysts reported in the
2
literature for preparation of 6-amino-4-aryl-3-methyl-1,4-dihydropyrano
[2,3-c]pyrazole-5-carbonitriles
Entry
Catalyst
Conditions
Time(min)
IsolatedYield (%)a
1
2
3
4
5
6
7
8
9
g-Alumina (15mol%)
H2O, 100°C
r.t
Solvent free,100 °C
50
20
5
20
5
30
10
10
10
7
80
97
85
89
80
92
96
87
90
97
96
97
(TEAA) ionic liquid (40 mol %)
Trichloroaceticacid (10 mol %)
Imidazole (50 mol%)
H O, 80°C
2
Ce(SO ) (10 mol %)
Solvent free,100 °C
H2O, 50 °C
4
2
Ultrasound irradiation
Nanosized MgO (62 mol %)
L-proline (5mol%)
Acetonitrile, r.t
EtOH, reflux
L-proline (5mol%)
H O, reflux
2
1
1
1
0
1
2
H PO /Al O (0.08 mol %)
Solvent free,100 ºC
Solvent free,100 °C
EtOH, rt
3
4
2
3
Cellulose
Ag/TiO nano thin films
10
18
2
Selected spectroscopic data of some products are
given below:
(400 MHz, (DMSO-d ): d = 1.76 (s, 3H, CH ), 4.87
6
3
(s, 1H, CH), 7.30-7.94 (m, NH and Ar)
2
6
-amino-1,4-dihydro-3-methyl-4-(2,4-
6-amino-1,4-dihydro-3-methyl-4-
dichlorophenyl)-1-phenylpyrano[2,3-c]pyrazole-5-
(naphthalen-2-yl)-1-phenylpyrano[2,3-c]pyrazole-
-
1
-1
carbonitrile (4f): IR (KBr, cm ): 3458, 3325, 2198,
5-carbonitrile (4m):IR (KBr, cm ):3390, 3200, 2180,
1
1
1
3
660; H NMR(400 MHz, (DMSO-d ): d = 1.77 (s,
1655; H NMR (400 MHz, (DMSO-d ): d = 1.76 (s, 3H,
6
6
H, CH ), 5.15 (s, 1H, CH), 7.32-7.43 (m, 5H, NH2
CH ), 4.88 (s, 1H, CH), 7.29 (br, 2H, NH ), 7.33-7.96
3
3
2
and ArH ), 7.47-7.51 (m, 2H, ArH), 7.61 (s, 1H, Ar
(m, 12H, Ar).
H), 7.77 (d, 2H, J=8.0 Hz, ArH).
6
-amino-1,4-dihydro-3-methyl-4-(4-
6
-amino-1,4-dihydro-3-methyl-4-(4-
methoxyphenyl)pyrano[2,3-c]pyrazole-5-carbonitrile
(4o): IR (KBr, cm ): 3455, 3320, 2190, 1654; H
-
1
1
methoxyphenyl)-1-phenylpyrano[2,3-c]pyrazole-5-
carbonitrile (4g): IR (KBr, cm ): 3392, 2933, 2197,
663; H NMR(400 MHz, (DMSO-d ): d = 1.80 (s,
H, CH ), 3.64 (s, 3H, OCH ), 4.64 (s, 1H, CH), 6.92
-
1
NMR(300 MHz, (DMSO-d ): d = 1.79 (s, 3H, CH ),
6
3
1
1
3
3.73 (s, 3H, OCH ), 4.55 (s, 1H, CH), 6.85 (br, 2H,
6
3
NH ), 6.88 (d, J= 9.0 Hz, 2H, Ar), 7.07 (d, J=9.0 Hz,
3
3
2
(
d, J= 8.0 Hz, 2H,Ar), 7.19 (br, 2H, NH ), 7.20 (d, J=
2H, Ar), 12.03 (s, 1H, NH).
2
8
8
.0 Hz, 2H, Ar), 7.33 (t, J= 8.0 Hz,1H, Ar), 7.50 (t, J=
.0 Hz, 2H, Ar), 7.80 (d, J= 8.0 Hz, 2H, Ar).
6-amino-1,4-dihydro-3-methyl-4-(2-
chlorophenyl)pyrano[2,3-c]pyrazole-5-carbonitrile
-1
1
6-amino-1,4-dihydro-3-methyl-4-(3-ethoxy-
(4p):IR (KBr, cm ):3470, 3240, 2180, 1638; H NMR
4
-hydroxyphenyl)-1-phenylpyrano[2,3-c]pyrazole-5-
(300 MHz, (DMSO-d6): d = 1.77 (s, 3H, CH ), 5.08
3
-
1
carbonitrile (4i): IR (KBr, cm ): 3420, 3329, 2195,
(s, 1H, CH), 6.99 (br, 2H, NH ), 7.18-7.43 (m, 4H,
2
1
1653; H NMR (400 MHz, (DMSO-d ): d = 1.29-1.32
Ar), 12.16 (s, 1H, NH).
6
(
(
(
t, 3H, J=7.2 HzCH ), 1.84 (s, 3H, CH ), 3.95-4.01
3
3
q, 2H, J=7.2 Hz CH ), 4.59 (s, 1H, CH), 6.62-7.80
CONCLUSION
2
m, NH and Ar ), 8.86 (s, 1H,OH).
2
In this research, we used Ag/TiO nano thin
2
6
-amino-1,4-dihydro-3-methyl-4-(biphenyl-
films for first time as a catalyst for the Synthesis
of dihydropyrano[2,3-c]pyrazole derivatives. The
efficient features of this protocol are simple
4
(
-yl)-1-phenylpyrano[2,3-c]pyrazole-5-carbonitrile
4l):IR (KBr, cm ):3471, 3328, 2185, 1645; H NMR
-1
1

819
IRANI et al., Orient. J. Chem., Vol. 33(2), 814-820 (2017)
performing reaction, cleaner reaction, use of green
and reusable nano catalyst. Satisfactory yields of
products, as well as a simple isolation and reduced
ACkNOꢃLEDGMENTS
We are thankful to the University of Sistan
reaction times of the products make it a useful and Baluchestan Research Council for the partial
protocol for the green synthesis. support of this research.
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