RSC Advances

View Article Online

PAPER
Published on 10 August 2015. Downloaded by UNIVERSIDAD ESTADUAL DE CAMPINAS on 27/01/2016 17:16:18.

View Journal | View Issue

Covalently anchored 2-amino ethyl-3-propyl

imidazolium bromideon SBA-15 as a green, efficient
Cite this: RSC Adv., 2015, 5, 75491
and reusable Brønsted basic ionic liquid
nanocatalyst for one-pot solvent-free synthesis of
benzopyranopyrimidines under ultrasonic
irradiation†
Mina Jafari Nasab and Ali Reza Kiasat*

Received 10th June 2015
Accepted 6th August 2015
DOI: 10.1039/c5ra11006h
www.rsc.org/advances
In the present study, highly ordered mesoporous SBA-15 having Brønsted basic ionic liquid pore channels was
synthesized via a surfactant-templated sol–gel methodology and a post modification process. For this, well
ordered mesoporous chloro-functionalized SBA-15, SBA-Cl, was first synthesized by the direct incorporation
of chloropropyl groups through the co-condensation of TEOS and CPTMS precursors in the presence of
Pluronic P123 triblock copolymer as a supramolecular template to direct the organization of polymerizing
silica. Subsequently, highly ordered 2-amino ethyl-3-propyl imidazolium bromide functionalized
mesoporous SBA-15, SBA-Im-NH2, with a high surface area was synthesized by a nucleophilic substitution
reaction of SBA-Cl with imidazole and then quaternization with 2-bromo ethylamine hydrobromide. The
target organic–inorganic nanocomposite was characterized by FT-IR spectroscopy, scanning electron
microscopy (SEM), transmission electron microscopy (TEM), X-ray diffraction (XRD), thermogravimetric
analysis (TGA), elemental analysis (CHN) and Brunauer–Emmett–Teller (BET) analysis. The SBA-Im-NH2
nanocomposite was successfully used as an efficient Brønsted basic ionic liquid nanocomposite for the
preparation of benzopyranopyrimidine derivatives by the one-pot pseudo four-components reaction of
salicylaldehydes, malononitrile and secondary amines under ultrasonic and solvent-free conditions at room
temperature. This method has the advantages of high yields, cleaner reaction, simple methodology, short
reaction times, easy work-up, and greener conditions. In addition to the facility of this methodology, the
catalyst also enhances product purity and promises economic as well as environmental benefits.

SBA-15 usually possess exclusive properties such as a large

1. Introduction
The exciting discovery of mesoporous and nanostructured silica-
based materials in the early 1990s evoked new windows for the
exploration in material research.1,2 Recently, enormous attention
has been directed toward the synthesis of this class of tunable
pore size mesoporous materials with different compositions and
pore apertures using a variety of templates and inorganic
precursors. Therefore, a new type of ordered mesoporous
material, i.e. SBA-15, with a honeycomb-like porous structure
containing hundreds of empty channels was developed by
employing amphiphilic triblock copolymers P123 as a structure-
directing agent.3,4 Owing to its convenient synthesis procedure,
stupendous mesoporous structure and surface silanol groups,
Chemistry Department, College of Science, Shahid Chamran University, Ahvaz,
61357-4-3169, Iran. E-mail: akiasat@scu.ac.ir; Fax: +98 61 33738044; Tel: +98 61
33738044
† Electronic supplementary information (ESI) available. See DOI:
10.1039/c5ra11006h
surface area, high pore volume, high thermal and hydrothermal
stability, uniform tubular channels with tunable pore diameter,
low mass density, non-toxic nature and is easily modiable.5,6 All
these excellent characteristics and exclusive properties make it
attractive in the elds of catalysis and functional materials.7–9
To develop this strategy, numerous scientists have recently
focused their interest on the modication of the inner pore
surfaces of SBA-15 with various organic functional groups to
render them suitable for specic applications.10–15
Green chemistry is increasingly seen as a powerful tool that
reduces the impact of chemistry on the environment by pre-
venting pollution at its source and using fewer natural
resources. To target this objective, ultrasound promoted reac-
tions have been increasingly used in synthetic organic chem-
istry. In addition of advantages, such as shorter reaction times,
milder reaction conditions, higher yields, improved selectivity
and clean reactions in comparison to classical methods,16–18 in
this green technique the reaction is carried out at a lower

This journal is © The Royal Society of Chemistry 2015 RSC Adv., 2015, 5, 75491–75499 | 75491
 View Article Online

RSC Advances Paper

external temperature relative to the usual thermal methods; the
possibility of the occurrence of undesired reactions is reduced,
and as a result of cleaner reaction work-up is easier.19
In spite of the signicant useful attributes of multicompo-
nent reactions (MCRs) for modern organic chemistry and their
Published on 10 August 2015. Downloaded by UNIVERSIDAD ESTADUAL DE CAMPINAS on 27/01/2016 17:16:18.
determined in open capillaries with a BUCHI 510 melting point
apparatus. The FT-IR spectra of the powders were recorded using
a BOMEM MB-Series 1998 FT-IR spectrometer. X-ray diffraction
(XRD) patterns of the samples were obtained on a Philips X-ray
diffraction model PW 1840. Transmission electron microscopy

suitability for building up large compound libraries, these
reactions were of limited interest in the past y years.
However, in the last decade, with the introduction of high-
through put biological screening, the importance of MCRs for
drug discovery has been recognized, and considerable efforts
from both academic and industrial researchers have been
focused, especially on the design and development of multi-
component procedures for the generation of libraries of
heterocyclic compounds.20 In this context, benzopyranopyr-
imidines show interesting features, which make them attractive
targets for the synthesis via MCRs.
Benzopyranopyrimidines demonstrate anti-inammatory,
anticonvulsant and analgesic activities, importantly in vitro anti-
aggregating activities,21 as well as pharmacological activities
such as antiviral,22 antimicrobial,23 antifungal,24 antioxidant,25
antileishmanial,26 antitumor,27 hypotensive,28 antiproliferation,29
local anesthetic,30 antiallergenic,31 central nervous system (CNS)
activities and effects,32 as well as treatment of Alzheimer's
disease33 and Schizophrenia disorder.34 Although to achieve suit-
able conditions for the synthesis of the benzopyranopyrimidines
various Lewis and protic acid catalysts in different solvents have
been previously investigated, but due to biological importance of
this class of compounds, nding an efficient and facile method is
still challenging.
Taking all these facts into account and as a part of our
ongoing interest in the synthesis of novel functionalized mes-
oporous silica and investigation of their applications as nano-
catalysts in the one-pot synthesis of biologically relevant
heterocyclic compounds,35 herein we have focused our interest
on the modication of the inner pore surfaces of mesoporous
SBA by the incorporation of Brønsted basic ionic liquid units to
render it suitable as an organized mesoporous tunable pore
nanocatalyst for green, rapid and efficient multicomponent
synthesis of benzopyranopyrimidine derivatives under ultra-
sonic and solvent-free conditions.
(TEM) images were obtained using a Zeisss-EM10C at 80 kV.
2.2. Synthesis of chloropropyl-graed SBA-15 (SBA-Cl)
Chloropropyl-graed SBA-15 (SBA-Cl) was prepared according to
the reported method.36 Pluronic 123 (4 g) was dissolved in 125 g
of 2.0 M HCl solution at room temperature. Then, TEOS (8.41 g,
40.41 mmol) was added and equilibrated at 40  C for prehy-
drolysis. To the mixture, CPTMS (1.3 g, 6.5 mmol) was slowly
added and stirred at 40  C for 20 h and reacted at 95  C under
static conditions for 24 h. The solid product was recovered by
ltration and dried at room-temperature overnight. The template
was removed from the as-synthesized material by reuxing in
95% ethanol for 48 h (1.5 g of the as-synthesized material per
400 mL of ethanol). Then, the product was ltered, washed
several times with water and ethanol, and dried at 50  C.
2.3. Synthesis of SBA-propyl-3-aminoethyl imidazolium
bromide, SBA-IM-NH2
To a solution of imidazole (0.476 g, 1 mmol) in 25 mL of dry
toluene, sodium hydride (0.167 g, 7 mmol) was added and
stirred under a nitrogen atmosphere at room temperature for
2 h to obtain sodium imidazole. Then, SBA-Cl (5.00 g) was
added and the mixture was reuxed under a nitrogen atmo-
sphere for 24 h. The resulting product was ltered and washed
with ethanol (3  20 mL) and dried under vacuum at 100  C for
8 h to obtain 3-(1-imidazole)propyl-SBA (SBA-Im).
To prepare SBA-propyl-3-aminoethyl imidazolium bromide,
SBA-IM-NH2, 0.6 g of SBA-Im was suspended in 25 mL of
acetonitrile. 2-Bromo ethyl amine hydrobromide (0.4 g, 2 mmol)
was added slowly and the mixture was reuxed at 80  C for 12 h.
The excess of 2-bromo ethyl amine hydrobromide was removed

2. Experimental
2.1. General
Tetraethyl orthosilicate (TEOS), 3-chloropropyltrimethoxysilane
(CPTMS), Pluronic P123 triblock copolymer (EO20 PO70 EO20,
MW ¼ 5800) and 2-bromo ethyl amine hydrobromide were
supplied by Aldrich. Other chemical materials were purchased
from Fluka and Merck companies and used without further
purication. The products were characterized by comparison of
their physical data, such as IR, 1H NMR and 13C NMR spectra,
with known samples. NMR spectra were recorded in CDCl3 on a
Bruker Advance DPX 400 MHz spectrometer using TMS as the
internal standard. The determination of the purity of the products
and reaction monitoring were performed by TLC on silica gel Poly
Gram SIL G/UV 254 plates. Elemental analysis was performed on a
Perkin-Elmer CHN-2400 analyzer. Melting points were Scheme 1 The synthesis route of SBA-IM-NH2.

75492 | RSC Adv., 2015, 5, 75491–75499 This journal is © The Royal Society of Chemistry 2015
 View Article Online

Paper RSC Advances

Published on 10 August 2015. Downloaded by UNIVERSIDAD ESTADUAL DE CAMPINAS on 27/01/2016 17:16:18.

Fig. 1 The FT-IR spectra of SBA-15, SBA-Cl and SBA-IM-NH2.

Table 1 Elemental compositions of sample analyzed using the CHN

technique

Samples C (wt%) N (wt%) H (wt%)

SBA-IM-NH2 13.2 3.2 4.5

Fig. 3 The TEM and SEM images of SBA-IM-NH2.

by ltration and washing with ethanol. The resulting solid was
washed with NaOH (0.03 g, 50 mmol) for neutralization and
dried in an oven at 80  C for 6 h under vacuum. The reaction
sequence and the possible structure of SBA-IM-NH2 are shown
in Scheme 1.
The basic capacity of the nanocomposite was determined by
potentiometry and conrmed by acid–base titration. Therefore,
SBA-IM-NH2 (0.1 g) was placed in an aqueous solution of NaCl
(1 M, 25 mL, initial pH ¼ 6) and the resulting mixture was stirred
for 24 h; the pH of the solution increased to 8.50. The basic
capacity of the nanocomposite is 2.5  104 mmol OH per gram
of composite. This result was also conrmed by back-titration.

2.4. General procedure for the synthesis of

benzopyranopyrimidines
Fig. 4 TGA-DTG analysis of SBA-IM-NH2.
A mixture of 2-hydroxybenzaldehyde (2 mL), malononitrile
(1 mL), secondary amine (1 mmol) and 0.005 g of SBA-IM-NH2

was reacted at room temperature under ultrasonic conditions.

Aer the completion of the reaction, as indicated by TLC, the
solid product was dissolved in CH2Cl2 and then the catalyst was
separated from the reaction mixture by centrifugation. Then,
solvent was removed by evaporation and the crude solid product
was puried by a recrystallization procedure in ethanol to
obtain the corresponding benzopyranopyrimidines as pure
products in good yields. To recover the catalyst, SBA-IM-NH2
was washed with CH2Cl2 and dried under reduced pressure.

3. Results and discussion

The route for the preparation of highly ordered mesoporous
Fig. 2 XRD pattern of SBA-IM-NH2. SBA-15 having Brønsted basic ionic liquid units, SBA-IM-NH2

This journal is © The Royal Society of Chemistry 2015 RSC Adv., 2015, 5, 75491–75499 | 75493
 View Article Online

RSC Advances Paper

Published on 10 August 2015. Downloaded by UNIVERSIDAD ESTADUAL DE CAMPINAS on 27/01/2016 17:16:18.

Fig. 5 Pore size distributions of SBA-Cl (a) and SBA-IM-NH2 (c) and nitrogen adsorption–desorption isotherms of SBA-Cl (b) and
SBA-IM-NH2 (d).

Table 2 Specific surface area (SBET), diameter pore and total pore Table 3 Optimization of the amount of the SBA-IM-NH2
volume nanocomposite

BET surface Diameter Pore volume Entry Catalyst (mg) Time (min) Yield (%)
Samples area (m2 g1) (nm) (cm3 g1)
1 — 60 —
SBA-Cl 753 9.72 1.25 2 2 20 70
SBA-IM-NH2 367.27 3.76 0.31 3 5 8 95
4 10 10 90

nanocomposite, is schematically illustrated in Scheme 1. The

SBA-Cl was initially synthesized by the direct incorporation of
chloropropyl groups through the co-condensation of
TEOS and CPTMS precursors in the presence of Pluronic
P123 triblock copolymer as a supra molecular template
to direct the organization of polymerizing silica.
Subsequently, 2-amino ethyl-3-propyl imidazolium bromide
functionalized mesoporous SBA-15, SBA-Im-NH2, was
synthesized by a nucleophilic substitution reaction of SBA-Cl
with imidazole and then quaternization with 2-bromo ethyl-
amine hydrobromide.

75494 | RSC Adv., 2015, 5, 75491–75499 This journal is © The Royal Society of Chemistry 2015
 View Article Online

Paper RSC Advances

Table 4 The preparation of benzopyranopyrimidines derivatives

Published on 10 August 2015. Downloaded by UNIVERSIDAD ESTADUAL DE CAMPINAS on 27/01/2016 17:16:18.

Entry X Amine Product Time (min) Yielda (%) mp ( C) found (reported)

1 H 10 80 178–180 (177–179)37

2 H 8 90 199–201 (197–199)38

3 H 10 93 201–203 (—)

4 H 10 85 185–189 (186–188)39

5 3-Cl 8 80 195–197 (197)40

This journal is © The Royal Society of Chemistry 2015 RSC Adv., 2015, 5, 75491–75499 | 75495
 View Article Online

RSC Advances Paper

Table 4 (Contd. )
Published on 10 August 2015. Downloaded by UNIVERSIDAD ESTADUAL DE CAMPINAS on 27/01/2016 17:16:18.

Entry X Amine Product Time (min) Yielda (%) mp ( C) found (reported)

6 3-Cl 5 95 246–250 (249–251)40

7 3-Cl 8 95 242–245 (—)

8 3-Cl 8 89 191–194 (192–195)41

9 2-OMe 15 65 190–192 (190)40

10 2-OMe 15 75 225–227 (224–226)38

75496 | RSC Adv., 2015, 5, 75491–75499 This journal is © The Royal Society of Chemistry 2015

Paper
Table 4 (Contd. )
Published on 10 August 2015. Downloaded by UNIVERSIDAD ESTADUAL DE CAMPINAS on 27/01/2016 17:16:18.
Entry X Amine Product
11 2-OMe
12 2-OMe
a
Isolated yields.
To characterize the catalyst, and to conrm the immobili-
zation of the active components on the pore surface, FT-IR
spectroscopy was utilized. The FT-IR spectra of the SBA-15,
SBA-Cl and SBA-IM-NH2 (Fig. 1) in the range of 400–4000
cm1 exhibited peaks at 1220, 1078, 804, and 470 cm1 related
to stretching, bending and vibration modes of Si–O–Si. In
addition, the FT-IR spectra of the SBA-IM-NH2 exhibited two
new peaks at 1560 and 1645 cm1, which were assigned to the
C]C and C]N bands of the imidazole rings, respectively. The
absorbance of the C–N stretching vibration is normally
observed around 1000–1200 cm1, which cannot be resolved
due to its overlap with the absorbance of Si–O–Si stretch. The
presence of amino groups in the SBA-IM-NH2 was further
corroborated by a broad band at 2800–3400 cm1 attributed to
the O–H vibration of the physically adsorbed water.
The graing of organic units to SBA-15 was also conrmed by
CHN analysis. The results of elemental analysis showed the
presence of carbon, nitrogen and hydrogen in SBA-Im-NH2
(Table 1).
The representative powder X-ray diffraction (XRD) patterns
of SBA-IM-NH2 are shown in Fig. 2. The low-angle XRD pattern
of SBA-IM-NH2 exhibits two weak lines (for 110 and 200) and a
single strong peak (100), which conrm the long range order
and excellent textural uniformity of the mesoporous material.
This journal is © The Royal Society of Chemistry 2015
View Article Online
RSC Advances
Time (min) Yielda (%) mp ( C) found (reported)
15 72 220–224 (—)
15 70 159–161 (158–160)39
The size and morphology of the SBA-IM-NH2 nanocomposite
was characterized by TEM and SEM (Fig. 3). The TEM images of
the organocatalyst indicate the mesoporous structure and
orderly pore arrangement, with an average diameter of
approximate 30 nm. It can be clearly seen that the samples
maintain the unique pore structure of the parent support,
SBA-15, very well.
Thermogravimetric analysis (TGA) was employed to deter-
mine the organic content of the graed silica and their thermal
stability. Fig. 4 shows the thermogravimetric analysis-derivative
thermogravimetric analysis (TGA-DTG) for SBA-IM-NH2. It can
be seen that SBA-IM-NH2 nanocomposite yielded about 9.2%
weight loss from ca. 25 to 195  C, which was attributed to the
desorption of physically adsorbed water as well as dehydration
of the surface –OH groups. The decline in the temperature
range from ca. 280 to 650  C should be ascribed to the removal
of the organic parts on the surface of the nanocomposite during
hydrothermal treatment. As shown in Fig. 4, the weight losses of
the organic parts are 0.277 g/g of the sample. Therefore, the
nanocatalyst is completely stable below 280  C and can be
applied without degradation.
Fig. 5 shows the characterization of surface area, pore
volume, and pore size distribution of SBA-Cl and SBA-IM-NH2,
which were determined through BET and BJH method from the
RSC Adv., 2015, 5, 75491–75499 | 75497

RSC Advances
Published on 10 August 2015. Downloaded by UNIVERSIDAD ESTADUAL DE CAMPINAS on 27/01/2016 17:16:18.
Fig. 6 Catalyst reusability.
adsorption of nitrogen at 77 K on a Micrometrics Gemini ana-
lyser. The hysteresis curves exhibited the characteristics of type
IV isotherm. The experimentally determined main structural
characteristics are listed in Table 2. The BJH pore size and the
surface areas of the samples ranged from 753 to 367.27 m2 g1.
Aer SBA-Cl loading, the surface areas decreased by approxi-
mately 48%, indicating that the SBA-Cl pores were occupied by
organic molecules. A corresponding decrease in the pore
volume of the SBA-IM-NH2 relative to the SBA-Cl by approxi-
mately 25% is also observed, which correlates with the presence
of organic molecules inside the SBA-Cl pores. The BJH pore size
distribution analysis shows that the material possesses
uniform-sized mesopores centered at ca. 97.2 Å for SBA-Cl and
centered at 37.6 Å for the SBA-IM-NH2 samples.
To investigate the catalytic activity of SBA-IM-NH2 as a
heterogeneous catalyst in the synthesis of benzopyranopyr-
imidines, the reaction of 2-hydroxy benzaldehyde, malononi-
trile and morpholine in a 2 : 1 : 1 molar ratio was selected as a
model system under ultrasonic conditions at room tempera-
ture. As shown in Table 3, the best result was obtained when the
reaction was carried out in the presence of 5 mg of SBA-IM-NH2.
With the optimized conditions in hand, we investigated the
use of a wide range of amines 3 and salicylic aldehydes 1 in this
pseudo four components condensation using 5 mg of SBA-IM-
NH2 under ultrasonic and solvent-free conditions at room
temperature, where the desired products were afforded in high
to excellent isolated yields (Table 4). With regard to substitu-
ents, both aldehydes with electron-withdrawing and electron-
donating groups participated in the reaction, but the former
reacted better.
Reusability of the SBA-IM-NH2 catalyst was tested by
consecutively recovering and then reusing the catalyst up to
four times. The reaction was carried out repeatedly under one
constant set of operating conditions (Fig. 6). Therefore, the
recyclability of catalyst makes the process economically and
potentially viable for commercial applications.
4. Conclusion
In the present study, a highly ordered mesoporous SBA-15
having Brønsted basic ionic liquid pore channels was
75498 | RSC Adv., 2015, 5, 75491–75499
View Article Online
Paper
synthesized via a surfactant-templated sol–gel methodology and
a post modication process. The catalytic activity of the basic
nanocomposite has been successfully applied for the one-pot
pseudo four-components reaction of salicylaldehydes, malono-
nitrile and secondary amines under ultrasonic and ambient
conditions. This solvent-less catalytic system certainly contrib-
utes to better environmental and green technology for the facile
preparation of the benzopyranopyrimidine derivatives. This
method offers several advantages including high yield, clean
reaction media, short reaction time, easy separation and recy-
clability of the solid catalyst.
Acknowledgements
We are grateful to the Research Council of Shahid Chamran
University for nancial support.
Notes and references
1 J. S. Beck, J. C. Vartuli, W. J. Roth, M. E. Leonowicz,
C. T. Kresge, K. D. Schmitt, C. T. W. Chu, D. H. Olson,
E. W. Sheppard, S. B. McCullen, J. B. Higgins and
J. L. Schlenker, J. Am. Chem. Soc., 1992, 114, 10834.
2 C. T. Kresge, M. E. Leonowicz, W. J. Roth, J. C. Vartuli and
J. S. Beck, Nature, 1992, 359, 710.
3 D. Y. Zhao, J. L. Feng, Q. S. Huo, N. Melosh,
G. H. Fredrickson, B. F. Chmelka and G. D. Stucky, Science,
1998, 279, 548.
4 X. Fan, J. Li, Z. Zhao, Y. Wei, J. Liu, G. Jiang and A. Duan, RSC
Adv., 2015, 5, 28305.
5 J. Jarupatrakorn and J. D. Tilley, J. Am. Chem. Soc., 2002, 124,
8380.
6 Y. M. Liu, J. Xu, L. He, Y. Cao, H. Y. He, D. Y. Zhao,
J. H. Zhuang and K. N. Fan, J. Phys. Chem., 2008, 112, 16575.
7 J. N. Li, L. N. Wang, T. Qi, Y. Zhou, C. H. Liu and J. L. Chu,
Microporous Mesoporous Mater., 2008, 110, 442.
8 E. A. Sujandi, D. S. Prasetyanto, S. C. Han and S. E. Lee Park,
Catal. Today, 2009, 141, 374.
9 J. N. Li, T. Qi, L. N. Wang, C. H. Liu and Y. Zhang, Mater. Lett.,
2007, 61, 3197.
10 A. Vinu, K. Z. Hossain and K. Ariga, J. Nanosci. Nanotechnol.,
2005, 5, 347.
11 (a) S. Jin Bæ, S. W. Kim, T. Hyeon and B. Moon Kim, Chem.
Commun., 2000, 31; (b) T. Luts, R. Frank, W. Suprun,
S. Fritzsche, E. Hey-Hawkins and H. Papp, J. Mol. Catal. A:
Chem., 2007, 273, 250.
12 T. Salesch, S. Bachmann, S. Brugger, R. Rabelo-Schaefer,
K. Albert, S. Steinbrecher, E. Plies, A. Mehdi, C. Reyé,
R. J. P. Corriu and E. Lindner, Adv. Funct. Mater., 2002, 2,
134.
13 (a) L. Mercier and T. J. Pinnavaia, Adv. Mater., 1997, 9, 500;
(b) X. Feng, G. E. Fryxxell, L. Q. Wang, A. Y. Kim, J. Liu and
K. M. Kemner, Science, 1997, 276, 923.
14 (a) W. Zhang, J. Wang, P. T. Tanev and T. J. Pinnavaia, Chem.
Commun., 1996, 979; (b) X. Feng, G. E. Fryxell, L. Q. Wang,
A. Y. Kim, J. Liu and K. M. Kemner, Science, 1997, 279, 923.
This journal is © The Royal Society of Chemistry 2015

Paper
15 (a) D. Moelans, P. Cool, J. Baeyens and E. F. Vansant, Catal.
Commun., 2005, 6, 591; (b) A. Galarneau, G. Renard,
M. Mureseanu, A. Tourrette, C. Biolley, M. Choi, R. Ryoo,
F. Di Renzo and F. Fajula, Microporous Mesoporous Mater.,
2007, 104, 103.
Published on 10 August 2015. Downloaded by UNIVERSIDAD ESTADUAL DE CAMPINAS on 27/01/2016 17:16:18.
16 J. P. Lorimer and T. J. Mason, Chem. Soc. Rev., 1987, 16, 239.
17 J. Safari, S. H. Banitaba and S. Dehghan Khalili, Ultrason.
Sonochem., 2012, 19, 1061.
18 J. Safari, S. H. Banitaba and S. D. Khalili, Ultrason.
Sonochem., 2013, 20, 401.
19 B. Datta and M. A. Pasha, Ultrason. Sonochem., 2013, 20, 303.
20 General Introduction–Multicomponent Reactions in Organic
Synthesis, ed. J. Zhu, Q. Wang and M. X. Wang, 2014.
21 K. C. Joshi, R. Jain, K. Sharma, S. K. Bhattacharya and
R. K. Goel, J. Indian Chem. Soc., 1988, 65, 202.
22 A. H. Shamroukh, M. E. A. Zaki, E. M. H. Morsy, F. M. Abdel-
Motti and F. M. E. Abdel-Megeid, Arch. Pharm., 2007, 340,
236.
23 (a) M. S. Mostafa, J. Environ. Sci., 2008, 36, 255; (b) F. A. Eid,
A. H. F. Abd El-Wahab, G. A. M. El-Hag Ali and
M. M. Khafagy, Acta Pharm., 2004, 54, 13; (c) A. H. Bedair,
H. A. Emam, N. A. El-Hady and K. A. R. Ahmed, Farmaco,
2001, 56, 965; (d) V. K. Ahluwalia, M. Chopra and
R. Chandra, J. Chem. Res., 2000, 162.
24 V. K. Akluwalia and M. Bala, Indian J. Chem., Sect. B: Org.
Chem. Incl. Med. Chem., 1996, 35, 742.
25 (a) L. Alvey, S. Prado, V. Huteau, B. Saint-Joanis, S. Michel,
M. Koch, S. T. Cole, F. Tillequin and Y. L. Janin, Bioorg.
Med. Chem., 2008, 16, 8264; (b) T. Symeonidis,
M. Chamilos, D. J. Hadjipavlou-Litina, M. Kallitsakis and
K. E. Litinas, Bioorg. Med. Chem. Lett., 2009, 19, 1139.
This journal is © The Royal Society of Chemistry 2015
View Article Online
RSC Advances
26 T. Narender, S. Shweta and S. Gupta, Bioorg. Med. Chem.
Lett., 2004, 14, 3913.
27 (a) S. J. Mohr, M. A. Chirigos, F. S. Fuhrman and J. W. Pryer,
Cancer Res., 1975, 35, 3750.
28 V. K. Tandon, M. Vaish, S. Jain, D. S. Bhakuni and
R. C. Srimal, Indian J. Pharm. Sci., 1991, 53, 22.
29 M. Brunavs, C. P. Dell, P. T. Gallagher, W. M. Owton and
C. M. Smith, Eur. Pat. Appl., 1993, 75, 557.
30 M. Longobardi, A. Bargagna, E. Mariani, P. Schenone and
E. Marmo, Rev. Bras. Farmacogn., 1990, 45, 399.
31 T. Narender, S. Shweta, S. Gupta, K. Gorlitzer, A. Dehre and
E. Engler, Arch. Pharm., 1983, 316, 264.
32 F. Eiden and F. Denk, Arch. Pharm., 1991, 324, 875.
33 C. Bruhlmann, F. Ooms, P. Carrupt, B. Testa, M. Catto,
F. Leonetti, C. Altomare and A. Cartti, J. Med. Chem., 2001,
44, 3195.
34 S. R. Kesten, T. G. Heffner, S. J. Johnson, T. A. Pugsley,
J. L. Wright and D. L. Wise, J. Med. Chem., 1999, 42, 3718.
35 J. Davarpanah and A. Kiasat, Catal. Commun., 2014, 46, 75.
36 X. Wang, K. S. K. Lin, J. C. C. Chan and S. Cheng, J. Phys.
Chem. B, 2005, 109, 1763.
37 R. Ghahremanzadeh, T. Amanpour and A. Bazgir,
Tetrahedron Lett., 2010, 51, 4202.
38 H. R. Shaterian and M. Aghakhanizadeh, Res. Chem.
Intermed., 2013, 39, 3877.
39 B. Umamahesh, T. R. Mandlimath and
K. I. Sathiyanarayanan, RSC Adv., 2015, 5, 6578.
40 A. Zonouzi, F. Hosseinzadeh, N. Karimi, R. Mirzazadeh and
S. W. Ng, ACS Comb. Sci., 2013, 15, 240.
41 S. Amirnejat, F. Movahedi, H. Masrouri, M. Mohadesi and
M. Z. Kassaee, J. Mol. Catal. A: Chem., 2013, 378, 135.
RSC Adv., 2015, 5, 75491–75499 | 75499