Succinimidinium hydrogensulfate ([H-Suc]HSO4) as an efficient ionic liquid catalyst for the synthesis of 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-trione and pyrano-pyrimidinones derivatives

Article abstract of DOI:10.1007/s13738-015-0754-1

In this work, succinimidinium hydrogensulfate ([H-Suc]HSO₄), a newly reported Br?nsted acidic ionic liquids is used as an efficient, homogeneous and reusable catalyst for the synthesis of 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-trione and pyrano[2,3-d]-pyrimidine dione derivatives. The products were formed in excellent yields over short reaction times and the catalyst can be reused several times without any appreciable loss in its activity.

Full text of DOI:10.1007/s13738-015-0754-1

J IRAN CHEM SOC
DOI 10.1007/s13738-015-0754-1
ORIGINAL PAPER
Succinimidinium hydrogensulfate ([H‑Suc]HSO4)
as an efficient ionic liquid catalyst for the synthesis
of 5‑arylidenepyrimidine‑2,4,6(1H,3H,5H)‑trione
and pyrano‑pyrimidinones derivatives
Omid Goli‑Jolodar1 · Farhad Shirini1 · Mohadeseh Seddighi1
Received: 29 June 2015 / Accepted: 24 September 2015
© Iranian Chemical Society 2015
Abstract In this work, succinimidinium hydrogensulfate
([H-Suc]HSO4), a newly reported Brönsted acidic ionic
liquids is used as an efficient, homogeneous and reus-
able catalyst for the synthesis of 5-arylidenepyrimidine-
2,4,6(1H,3H,5H)-trione and pyrano[2,3-d]-pyrimidine
dione derivatives. The products were formed in excellent
yields over short reaction times and the catalyst can be
reused several times without any appreciable loss in its
activity.
replace traditional mineral liquid acids, such as sulfuric
acid and hydrochloric acid [1]. For example it has been
reported that many organic reactions, such as esterification
[2–4], alkylation [5], alcoholysis [6], acylation [7], Claisen-
Schmidt condensation [8], carbonylation [9], nitration [10]
and hydrolyzation [11] can be accelerated in the presence
of the functionalized Brønsted acidic ILs.
5-Arylidenepyrimidine-2,4,6(1H,3H,5H)-trione
(A)
and pyrano-pyrimidinones (B) as two important deriva-
tives of barbituric acid show considerable pharmaceutical
and biological activities including anticonvulsant, sedative-
hypnotic, antiparkinsonian, antitumor, hepatoprotective,
antimalarial, analgesics, antifungal, antibacterial and antial-
lergic [12–26] activities. Furthermore, 5-monosubstituted
barbituric acids are precursors for the synthesis of a large
number of annulated uracils of biological significance.
Keywords Ionic liquids (ILs) · Succinimidinium
hydrogensulfate ([H-Suc]HSO4) · Barbituric acid ·
5-Arylidenepyrimidine-2,4,6(1H,3H,5H)-trione ·
Pyrano[2,3-d]-pyrimidine dione
Introduction
The development of environmentally friendly catalysts
and solvents for organic reactions is an area of consider-
able importance. In this area and from both economic and
environmental points of view, the use of non-volatile sol-
vents and non-metallic catalysts is very promising. In the
past few decades, and because of the fascinating properties
such as their low vapor pressure, reusability, high thermal
and chemical stability, ionic liquids (ILs) were successfully
used as environmentally benign solvents and catalysts in
numerous catalytic reactions. Among these types of com-
ponds, Brönsted acidic ionic liquids have been planned to
Because of the above mentioned applications, many
methods using different types of catalysts are reported for
the preparation of 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-
trione and pyrano[2,3-d]pyrimidinones derivatives which
of them Nickel nanoparticles [25], sodium p-toluene sul-
fonate (NaPTSA) [26], basic alumina [27], IR lamp [28],
Ce1MgxZr1-xO2 (CMZO) [29], l-proline [30], Zn[(L)pro-
line]2 [31], [BMIm]BF4 [32], 1,4-dioxane [33, 34], Diam-
monium hydrogen phosphate (DAHP) [35], SBA-Pr-SO3H
[36], Tetra-n-butylammonium bromide (TBAB) [37],
* Farhad Shirini
shirini@guilan.ac.ir
1
Department of Chemistry, College of Science, University
of Guilan, Rasht 41335, Islamic Republic of Iran
1 3

J IRAN CHEM SOC
1,4-Diazabicyclo[2.2.2]octane (DABCO) [38], are exam-
ples. However, many of these methods suffer from dis-
advantages such as low yields, long reaction times, harsh
reaction conditions, tedious work-up and requirement of
excess amounts of reagents or catalysts. Therefore, it is
important to find more convenient methods for the synthe-
sis of these types of compounds.
2 × 5 mL ether and dried under vacuum. After this process
[H-Suc]HSO4 was obtained as a cream solid (1.94 g, 97 %)
(M.P. 78–80 °C) (Scheme 1).
General procedure for the preparation
of 5‑arylidenepyrimidine‑2,4,6(1H,3H,5H)‑trione
A mixture of an aldehyde (1 mmol), barbituric acid
(1 mmol) and [H-Suc]HSO4 (0.009 g) in water (4 mL) was
heated in an oil bath (50 °C). After completion of the reac-
tion, as monitored by TLC [eluent: n-hexane:EtOAc (1:4)]
the crude product was filtered off, washed with water and
recrystallized from ethanol to offered the pure compound.
Experimental
General
Chemicals were purchased from Fluka, Merck, and Aldrich
chemical companies. All yields refer to the isolated products.
Products were characterized by comparison of, their physical
constants, IR and NMR spectroscopy with authentic samples
and those reported in the literature. The purity determination
of the substrate and reaction monitoring were accompanied
by TLC on silicagel polygram SILG/UV 254 plates.
General procedure for the preparation of pyrano[2,3‑d]
pyrimidinones
A solution of an aldehyde (1 mmol), malononitrile
(1.2 mmol), barbituric (1 mmol) and [H-Suc]HSO4
(0.009 g) in water (4 mL) was heated in an oil bath (80 °C).
After completion of the reaction, as monitored by TLC
[eluent: n-hexane:EtOAc (1:4)] the crude product was fil-
tered off, washed with water and recrystallized from etha-
nol to offered the pure compound.
Instrumentation
The IR spectra were recorded on a Perkin Elmer 283 B,
781 and 843 Spectrophotometers and FT-IR spectra were
recorded on a perkin-Elmer spectrum BX series and Thermo
Nicolet Nexus 670 Spectrophotometers. In all the cases the
1H NMR and 13C NMR spectra were recorded with Varian
Gemini 300 and 200 and BrukerAvance 400 and 300 MHz
instruments, respectively. All chemical shifts are quoted in
parts per million (ppm) relative to TMS using deuterated
solvent. The MS were measured on a Agilent Technology
(HP) manufacturer company under 70 eV conditions.
Spectral data of derivatives of 5-arylidenepyrimidine-2,
4,6(1H,3H,5H)-triones:
5-(2-Nitrobenzylidene)pyrimidine-2,4,6(1H,3H,5H)-
trione (Table 2, entry 5): White solid, M.p. 276–278 °C;
FT-IR(KBr) ν = 3427, 3318, 3181, 2956, 2892, 1678,
1
1574, 1519, 1350, 790; MS: m/z = 261 (M++1); HNMR
(400 MHz, DMSO-d6) δ = 7.58 (d, J = 7.6, 1H), 7.68 (dt,
J1 = 8, J2 = 0.8, 1H), 7.79 (dt, J1 = 7.6, J2 = 1.2, 1H),
8.24 (dd, J1 = 8, J2 = 1.2, 1H), 8.61 (s, 1H, HC = C),
11.26 (NH, s, 1H), 11.51(NH, s, 1H); 13CNMR (400 MHz,
Preparation of succinimidinium hydrogensulfate
([H‑Suc]HSO4) [36]
Table 1 Optimization of the reaction conditions catalyzed by
[H-Suc]HSO4
In a round-bottomed flask, 0.53 mL sulfuric acid (98 %,
d = 1.84) was added drop-wise to a mixture of succinim-
ide (0.99 g, 10 mmol) in 50 mL of dichloromethane on an
ice bath. The reaction mixture was stirred at room tem-
perature for 30 min, and then the solvent was evaporated
under reduced pressure. The solid residue was washed with
Entry Catalyst Solvent
(mg)
Temperature (°C) Time Yield (%)a
(min)
1
2
3
4
5
20
20
20
20
20
CH3CN
Reflux
60
60
40
6
40
n-Hexan Reflux
35
EtOH
H2O
Reflux
Reflux
85
95
Solvent- 100
free
60
Trace
6
10
5
H2O
H2O
H2O
H2O
H2O
Reflux
7
20
7
95
7
Reflux
Reflux
50
92
8
30
10
10
96
9
7
94
10
r.t.
120
Trace
a
Scheme 1 Preparation of [H-Suc]HSO4
Isolated yields
1 3

J IRAN CHEM SOC
DMSO-d6) δ = 120.9, 124.5, 130.6, 130.8, 132.1, 134.2,
146.7, 150.7, 152.9, 161.6, 162.8.
DMSO-d6) δ = 120.3, 128.0, 132.9, 135.9, 137.6, 150.6,
153.9, 161.9, 163.6.
5,5′-(1,3-Phenylenebis(methanylylidene))bis(pyrimid
ine-2,4,6(1H,3H,5H)-trione) (Table 2, entry 17): Yellow
solid, M.p. > 300 °C; FT-IR(KBr) ν = 3535, 3201, 3074,
1757, 1682, 1571, 800, 682; MS: m/z = 354 (M+); 1HNMR
(400 MHz, DMSO-d6) δ = 7.55 (t, J = 7.6, 1H), 8.20 (dd,
J1 = 7.8, J2 = 1.6, 2H), 8.29 (s, 2H, HC = C), 8.49 (s, 1H),
11.29 (NH, s, 2H), 11.44 (NH, s, 2H); 13CNMR (400 MHz,
5,5′-(1,4-Phenylenebis(methanylylidene))bis(pyrimid
ine-2,4,6(1H,3H,5H)-trione) (Table 2, entry 18): Yellow solid,
M.p. > 300 °C; FT-IR(KBr) ν = 3495, 3202, 3085, 1749, 1685,
1584, 808; MS: m/z = 354 (M+); 1HNMR (400 MHz, DMSO-
d6) δ = 8.05 (s, 4H), 8.29 (s, 2H, HC = C), 11.30 (NH, s, 2H),
11.45 (NH, s, 2H) ppm; 13CNMR (400 MHz, DMSO-d6)
δ = 120.9, 129.0, 132.3, 136.1, 150.6, 153.4, 161.9, 163.6 ppm.
Scheme 2 [H-Suc]HSO4 catalyzed the synthesis of 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-trione
Table 2 Preparation of
Entry
Aldehyde
Time (min)
Yield (%)a
Mp °C
Found
5-arylidenepyrimidine-
2,4,6(1H,3H,5H)-trione
derivatives using [H-Suc]HSO4
as the catalyst
Repored(ref.)
1
C6H5CHO
5
7
96
90
93
92
94
90
91
92
94
93
92
96
93
87
255–256
261–263
265–267
249–250
276–278
272–274
213–215
228–230
298–300
292–293
>300
256 [25]
2
2-ClC6H4CHO
2-MeOC6H4CHO
2-OHC6H4CHO
2-NO2C6H4CHO
3-ClC6H4CHO
3-MeC6H4CHO
3-NO2C6H4CHO
4-ClC6H4CHO
4-BrC6H4CHO
4-OHC6H4CHO
4-MeOC6H4CHO
4-NO2C6H4CHO
4-NMe2C6H4CHO
268 [26]
3
7
268–269 [27]
249–251 [45]
–
4
7
5
5
6
7
274–278 [46]
– [24]
7
7
8
5
231–233 [45]
298.5 [25]
292–293 [25]
>300 [25]
306–308 [29]
272–274 [45]
281–282 [29]
9
7
10
11
12
13
14
7
10
3
297–300
270–272
278–279
10
7
15
7
90
270–273
268 [25]
16
5
91
266 (dec)
266 (dec) [25]
17
15
15
88
90
>300
>300
–
–
18
a
Isolated yields
1 3

J IRAN CHEM SOC
After optimization of the reaction conditions and in
order to explore the scope of this method, the condensa-
tion of barbituric acid with different types of aryl aldehydes
in the presence of [H-Suc]HSO4 (10 mg) was investigated
under the selected conditions. The studied reactions yielded
the desired 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-trione
derivatives during very short reaction times (3–15 min) in
excellent yields.
The study on the influence of electron-withdrawing and
electron-donating substituents on the aromatic ring of alde-
hydes upon the reaction times and yields showed that the
changing of the substituents had a negligible effect on the
reaction results (Table 2). Using this method unsaturated
aldehydes, were also successfully converted to the desired
products in high yields (Table 2, entry 15).
This method was also found to be useful for the usage
of dialdehydes. In this reaction, 2 equivalents of barbituric
acid successfully condensed with 1 equivalent of isoph-
thalaldehyde and/or terephthalaldehyde and the desired
products were obtained in high yields during acceptable
reaction times. This result shows the practical synthetic
efficiency of this reaction (Table 2, entry 17, 18).
In the next step, [H-Suc]HSO4 was used in the synthe-
sis of pyrano[2,3-d]pyrimidinones from the condensation
of barbitoric acid, malononitrile and aldehydes. In order
to optimize the reaction conditions, the condensation
of 4-chlorobenzaldehyde (1 mmol) with barbituric acid
(1 mmol) and malononitrile was studied in the presence
of [H-Suc]HSO4 (10 mg), and the results are tabulated in
Results and discussion
In continuation of the successful design, synthesis and
application of ILs in organic chemistry [39–43], very
recently we have reported the preparation of succinimi-
dinium hydrogen sulfate ([H-Suc]HSO4) and its applicabil-
ity in the acceleration of the N-Boc protection of amines
[44]. The obtained results in this study clarified that this
reagent is able to catalyze the reactions which need the
acidic catalyst to speed-up. On the basis of these results we
were interested in investigating the applicability of this rea-
gent in the promotion of the synthesis of the barbituric acid
derivatives.
At first, we focused our attention on the synthesis of
5-arylidenepyrimidine-2,4,6(1H,3H,5H)-triones. For opti-
mization of the reaction conditions, the condensation of
4-chlorobenzaldehyde with barbituric acid to the corre-
sponding product was selected as a model reaction. For this
purpose various conditions using different amounts of the
catalyst and temperatures under solvent-free conditions or
different types of solvents were examined (Table 1). After
careful studies the optimal reaction conditions for this reac-
tion was selected as follow: 1 mmol aldehyde, 1 mmol
barbituric acid and 10 mg [H-Suc]HSO4 as the catalyst
at 50 °C in water as the solvent (Scheme 2). It is impor-
tant to note that lower amounts of the catalyst led to the
lower yields, while higher amounts of [H-Suc]HSO4 did
not affect the reaction yields. Nearly no product could be
detected in the absence of the catalyst.
Table 3 Optimization of the
reaction conditions catalyzed by
Entry
Catalyst (mg)
Solvent
Temperature (°C)
Time (min)
Yield (%)a
[H-Suc]HSO4
1
2
3
4
5
6
7
8
10
10
10
10
10
20
10
10
CH3CN
n-Hexan
EtOH
Reflux
Reflux
Reflux
Reflux
100
120
120
60
9
Mixture of product
Mixture of product
85
H2O
95
Solvent-free
H2O
60
8
Mixture of product
Reflux
50
95
76
95
H2O
30
10
H2O
80
a
Isolated yields
Scheme 3 [H-Suc]HSO4 catalyzed the synthesis of pyrano[2,3-d]pyrimidinones
1 3

J IRAN CHEM SOC
Table 4 Preparation of
pyrano[2,3-d]pyrimidinones
derivatives using [H-Suc]HSO4
as the catalyst
Entry
Aldehyde
Time (min)
Yield (%)a
Mp °C
Found
Reported (ref.)
1
2
C6H5CHO
8
11
10
15
13
10
10
10
8
92
98
95
95
90
98
95
98
98
92
215–217 224–225
[31]
2-ClC6H4CHO
2-NO2C6H4CHO
2-OHC6H4CHO
3-ClC6H4CHO
3-NO2C6H4CHO
4-ClC6H4CHO
4-BrC6H4CHO
4-OCH3C6H4CHO
4-NO2C6H4CHO
211–212 213–215
[47]
3
253–256 262–263
[44]
4
160–162 162–163
[48]
5
240–241 240–241
[37]
6
267–269 268–270
[30]
7
245–247 243–246
[36]
8
231–233 230–231
[37]
9
280–281 280–281
[47]
10
8
236–237 237–238
[31]
11
12
4-CH3C6H4CHO
4-NMe2C6H4CHO
12
10
85
98
225–227 225
231–233 230–232
[48]
a
Isolated yields
Tables 3. On the basis of these results, the optimized condi-
tions are selected as shown in Schemes 3.
with the other procedures such as long reaction times,
low yields, and hard conditions for the catalyst prepara-
tion, using infrared or microwave irradiation and high
catalyst loading.
To check the reusability of the catalyst, the reaction
of 4-chlorobenzaldehyde with barbituric acid and malo-
nonitrile under the optimized reaction conditions was
studied again. After separation of the product the cata-
lyst was recovered by evaporation of water, washed with
diethyl ether, dried at 50 °C under vacuum for 1 h, and
reused in another reaction with only slim reduction in
the catalytic activity. This method was used at least for
5 runs and the obtained yields were above 90 % (Fig. 1).
After determination of the optimized temperature, a
series of aromatic aldehydes bearing electron withdrawing
or donating groups were reacted with barbitoric acid and
malononitrile producing pyrano[2,3-d]pyrimidinones in
short reaction times (8–15 min) with high yields (Table 4).
In a plausible mechanism, the aldehyde is firstly acti-
vated by [H-Suc]HSO4. Next, the carbonyl group is
attacked by barbituric acid and the related 5-arylidenep-
yrimidine-2,4,6(1H,3H,5H)-trione products (A) were
formed. The subsequent addition of malononitrile to
Knoevenagel products (A), gives the acyclic adduct inter-
mediate, which undergoes intramolecular cyclization to
afford the pyrano[2,3-d]pyrimidinones (B) derivatives
(Scheme 4).
Conclusions
In order to highlight the merits of our newly developed
procedures, in Table 5 we have compared our results
obtained from the synthesis of 5-(4-chlorobenzylidene)
pyrimidine-2,4,6(1H,3H,5H)-trione (Table 2, entry
9) and 7-amino-5-(4-nitrophenyl)-2,4-dioxo-1,3,4,5-
tetrahydro-2H-pyrano[2,3-d]pyrimidine-6-carbonitrile
(Table 4, entry 10) catalyzed by [H-Suc]HSO4 with other
results reported in the literature. As shown in Table 5,
this method avoids some of the disadvantages associated
In conclusion, in this article, we have introduced a Brøn-
sted acidic ionic liquid named as succinimidium hydrogen-
sulfate ([H-Suc]HSO4) as a novel, highly efficient, general
and homogeneous catalyst for the synthesis of 5-arylide-
nepyrimidine-2,4,6(1H,3H,5H)-trione and pyrano[2,3-d]
pyrimidinones derivatives. The promising reasons for the
presented protocol is efficiency, generality, high yields of
the products, short reaction times, cleaner reaction profile,
1 3

J IRAN CHEM SOC
Scheme 4 Synthesis of com-
pounds (A) and (B)
(A)
(B)
Table 5 Comparison of the results obtained from the synthesis of 5-
(4-chlorobenzylidene) pyrimidine-2,4,6(1H,3H,5H)-trione, 7-amino-
5-(4-nitrophenyl)-2,4-dioxo-1,3,4,5-tetrahydro-2H-pyrano[2,3-d]
pyrimidine-6-carbonitrile in the presence of [H-Suc]HSO4 with those
obtained using other catalysts
Product
Catalyst
Reaction conditions
Time (min)
Yield (%)
References
PVP-Ni nanoparticles
Non-catalyst
NaPTSA
ethylene glycol/50 °C
Infrared irradiation
r.t.
5
45
4
93
62
92
92
94
94
73
92
72
90
80
92
92
[23]c
[26]a, d
[24]e
[25]d
[27]d
Basic alumina
CMZO
MW (at 700 W)
MW (at 450 W)
Water/50 °C
3
3
[H-Suc]HSO4
l-proline
7
This work
[28]a, b
[29]a
[32]a, b
[33]a
[34]a
[35]a
aq. EtOH, r.t.
EtOH/reflux
45
30
120
15
35
120
8
Zn[(L)proline]2
DAHP
aq. EtOH/r.t.
SBA-Pr-SO3H
TBAB
Neat/140 °C
H2O/reflux
DABCO`
Ethanol-H2O (1:1)/r.t
Water/80 °C
[H-Suc]HSO4
This work
Draw backs:
a
Long reaction time
b
Low yields
c
Hard conditions for the catalyst preparation
Using Infrared or Microwave irradiation
High catalyst loading
d
e
1 3

J IRAN CHEM SOC
16. E.M. Griva, S. Lee, C.W. Siyal, D.S. Duch, C.A. Nichol, J. Med.
Chem. 23, 327 (1980)
17. G.L. Anderson, J.L. Shim, A.D. Broom, J. Org. Chem. 41, 1095
(1976)
18. S. Furuya, T. Ohtaki, Chem. Abstr. 121(1994), 205395 (1994)
19. D. Heber, C. Heers, U. Ravens, Pharmazie. 48, 537 (1993)
20. J. Davoll, J. Clarke, E.F. Eislager, J. Med. Chem. 15, 837 (1972)
21. E. Kretzschmer, Pharmazie. 35, 253 (1980)
22. V.K. Ahluwalia, R. Batla, A. Khurana, R. Kumar, Indian J.
Chem. Sec. 29, 1141 (1990)
23. M.M. Ghorab, A.A.Y. Hassan, Phosphorus Sulfur Silicon Relat.
Elem. 141, 251 (1998)
24. N. Kitamura, A. Onishi, Eur. Pat, Chem. Abstr. 104(1984),
186439 (1984)
25. J.M. Khurana, K. Vij, Catal. Lett. 138, 104 (2010)
26. S. Kamble, G. Rashinkar, A. Kumbhar, K. Mote, R. Salunkhe,
Arch. Appl. Sci. Res. 2, 217 (2010)
27. A. Khalafi-Nezhad, A. Hashemi, Iran J. Chem. Chem. Eng. 20, 9
(2001)
28. G. Alcerreca, R. Sanabria, R. Miranda, G. Arroyo, J. Tamariz, F.
Degado, Synth. Commun. 30, 1295 (2000)
Fig. 1 Reusability of the catalyst
29. S.B. Rathod, A.B. Gambhire, B.R. Arbad, M.K. Lande, Bull.
Korean Chem. Soc. 31, 339 (2010)
30. M. Bararjanian, S. Balalaie, B. Movassagh, A.M. Amani, J. Iran.
Chem. Soc. 6, 436 (2009)
simplicity, low cost, ease of preparation and recycling of
the catalyst.
31. M.M. Heravi, A. Ghods, K. Bakhtiari, F. Derikvand, Synth.
Commun. 40, 1927 (2010)
Acknowledgments We are thankful to the University of Guilan
32. J. Yu, H. Wang, Synth. Commun. 35, 3133 (2005)
33. Y.A. Sharanin, G.V. Klokol, Zh Org Khim. 20, 2448 (1984)
34. H.H. Zoorob, M. Abdelhamid, M.A. El-Zahab, M. Abdel-Mogib,
I. AMA Arzneim Forsch. 47, 958 (1997)
Research Council for the partial support of this work.
References
35. S. Balalaie, S. Abdolmohammadi, H.R. Bijanzadeh, A.M.
Amani, Mol. Divers. 12, 85 (2008)
36. G.M. Ziarani, S. Faramarzi, S. Asadi, A. Badiei, R. Bazl, M.
Amanlou, DARU J. Pharm Sci. 21, 3 (2013)
37. A. Mobinikhaledi, M.A. Bodaghi Fard, Acta Chim. Slov. 57, 931
(2010)
38. J. Azizian et al., Orient. J. Chem. 28(1), 327 (2012)
39. F. Shirini, N.G. Khaligh, S. Akbari-Dadamahaleh, J. Mol. Catal.
A Chem. 365, 15 (2012)
1. V.I. Parvulescu, C. Hardacre, Chem. Rev. 107, 2615 (2007)
2. F.J. Hernandez-Fernandez, A.P. delos Rios, L.J. Lozano-Blanco,
C. Godinez, J. Chem. Technol. Biotechnol. 85, 1423 (2010)
3. Y.W. Zhao, J.X. Long, F.G. Deng, X.F. Liu, Z. Li, C.G. Xia, J.J.
Peng, Catal. Commun. 10, 732 (2009)
4. M.H. Han, W.L. Yi, Q. Wu, Y. Liu, Y.C. Hong, D.Z. Wang, Biore-
sour. Technol. 100, 308 (2009)
40. F. Shirini, M. Abedini, M. Seddighi, O.G. Jolodar, M.S.N. Lan-
groodi, S. Zamani, RSC Adv. 4, 63526 (2014)
41. M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, Org.
Prep. Proced. Int. 42, 95 (2010)
5. X.H. Yuan, M. Chen, Q.X. Dai, X.N. Cheng, Chem. Eng. J. 146,
266 (2009)
6. D. Jiang, Y.Y. Wang, M. Tu, L.Y. Dai, Chin. Chem. Lett. 19, 889
(2008)
42. M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, G. Chehar-
doli, F. Derakhshan-Panah, A. Zare, O. Khaledian, Scientia Iran-
ica 19, 1584 (2012)
43. M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, Z.
Asgari, V. Khakyzadeh, A. Hasaninejad, J. Indust. Eng. Chem.
19, 721 (2013)
7. P. Elavarasan, K. Kondamudi, S. Upadhyayula, Chem. Eng. J.
166, 340 (2011)
8. J.H. Shen, H. Wang, H.C. Liu, Y. Sun, A.M. Liu, J. Mol. Catal. A
Chem. 280, 24 (2008)
9. A.L. Lapidus, O.L. Eliseev, Solid Fuel Chem. 44, 197 (2010)
10. D. Fang, Q.R. Shi, J. Cheng, K. Gong, Z.L. Liu, Appl. Catal. A.
Gen. 345, 158 (2008)
11. Q.W. Yang, Z.J. Wei, H.B. Xing, Q.L. Ren, Catal. Commun. 9,
1307 (2008)
12. L. S. Goodman, A. Gilman, Mc Graw-Hill; New Delhi, p. 358
(1991)
13. G. Andrews, Medical pharmacology. p. 243 (1976)
14. WO. Foye, Principles of medicinal chemistry. PA. 143 (1989)
15. P. Kumar, C. Nath, J.C. Agarwal, K.P. Bhargava, K. Shanker,
Indian J. Chemistry B. 22B, 955 (1983)
44. F. Shirini, O.G. Jolodar, M. Seddighi, H. Takbiri Borujeni, RSC
Adv. 5, 19790 (2015)
45. C.S. Reddy, A. Nagaraj, P. Jalapathi, Indian J. Chem. 46B, 660
(2007)
46. J.T. Li, H.G. Dai, D. Liu, T.S. Li, Synth. Commun. 36, 789
(2006)
47. S. Mashkouri, M.R. Naimi-Jamal, Molecules 14, 474 (2009)
48. H. Kefayati, M. Valizadeh, A. Islamnezhad, Anal. Bioanal. Elec-
trochem. 6, 80 (2014)
1 3