Efficient synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones in the presence of nanocomposites under microwave irradiation

Article abstract of DOI:10.1016/j.molcata.2014.02.013

The preparation of quinazolinones has been developed by the condensation of aromatic aldehydes and 2-aminobenzamide in the presence of transition metal-CNTs nanocomposites as novel and recyclable catalyst under microwave and solvent-free conditions. This methodology provides a high speed path for the green and mild synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones with high structural diversity. The present methodology has advantages such as high activity and reusability of catalysts, heterogeneous nature of catalysts, no use of hazardous organic solvents and green conditions.

Full text of DOI:10.1016/j.molcata.2014.02.013

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Efficient synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones in the
presence of nanocomposites under microwave irradiation
Javad Safari∗, Soheila Gandomi-Ravandi
Laboratory of Organic Compound Research, Department of Organic Chemistry, College of Chemistry, University of Kashan, PO Box: 87317-51167, Kashan,
Islamic Republic of Iran
a r t i c l e i n f o
a b s t r a c t
Article history:
The preparation of quinazolinones has been developed by the condensation of aromatic aldehydes and
2-aminobenzamide in the presence of transition metal-CNTs nanocomposites as novel and recyclable
catalyst under microwave and solvent-free conditions. This methodology provides a high speed path for
the green and mild synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones with high structural diversity.
The present methodology has advantages such as high activity and reusability of catalysts, heterogeneous
nature of catalysts, no use of hazardous organic solvents and green conditions.
Received 12 December 2013
Received in revised form 4 February 2014
Accepted 6 February 2014
Available online xxx
Keywords:
Quinazolinones
Co-MWCNTs
© 2014 Elsevier B.V. All rights reserved.
Green chemistry
Microwave irradiation
Nanocomposites
1. Introduction
o-azidobenzamide with aldehydes and ketones [25]. Among the
diverse synthetic methods for the preparation of 2,3-dihydro-
Natural and synthetic quinazolinone derivatives constitute an
important class of fused heterocycles, which influence numer-
ous cellular processes. These scaffolds as a core unit have been
extensively studied in a number of biologically active compounds
because of their broad range of biological, medicinal, physiological
and pharmacological properties and their potential clinical applica-
tions [1–14]. Thus, extensive efforts have been exerted to develop
methodology for the synthesis of quinazolinone derivatives. A vari-
ety of synthetic methods have been extended for the synthesis of
quinazolinones and aryl-substituted quinazolinones included ami-
dation of 2-aminobenzonitrile followed by oxidative ring closure
[15], catalytic heterocyclization of nitoarenes [16], reduction of
the azide functionality [17] and cyclization of oacylaminobenza-
mides [18]. The other methods are such as solid-phase synthesis
of 2-arylamino-substituted quinazolinones [19] and preparation
from isatoic anhydrides and Schiff bases [20]. Also, a literature
survey showed that many methods were reported for the syn-
thesis of 2,3-dihydro-2-aryl-4(1H)-quinazolinones [21–23]. These
methods involve condensation of o-aminobenzamide with ben-
zyl [24] and also reductive cyclization of o-nitrobenzamide or
2-aryl-4(1H)-quinazolinones, the most popular method includes
condensation of derivatives of o-aminobenzamide with struc-
turally diverse aldehydes or ketones [21]. The antitumor activities
of a number of 2,3-dihydro-2-aryl-4-quinazolinone derivatives
were designated for the first time over three decades ago [26,27].
2-phenyl-4-quinazolinones exhibit a wide range of biological
activities such as cytotoxicity as potent tubulin polymerization
inhibitors [28]. Therefore, 2,3-dihydro-2-phenylquinazolin-4(1H)-
ones are inhibitors of tubulin polymerization with impressive
antiprolivative activity against several human cancers with IC50
value in nano molar concentration. They act like colchicine
(inhibitors of tubulin polymerization) by binding to ␣,␤-tublin [28].
Recently, also these analogs have been evaluated as antimitotic
agents [29]. Due to the biological and pharmaceutical importance
of quinazolinone derivatives, it has a great importance to develop
greener process for the synthesis of 2,3-dihydro-2-aryl-4(1H)-
quinazolinones.
Recently, much attention has been attracted to the usage of
carbon nanotubes (CNTs) in composite materials. Carbon nano-
tubes with unique morphology, good chemical stability and high
electrical conductivity are ideal materials to support heteroge-
neous catalysis [30]. Many studies have been developed to decorate
metal nanoparticles on the CNTs, which lead to optimal prop-
erties and superior performance [30,31]. The nanosized metallic
∗
Corresponding author. Tel.: +98 361 591 2320; fax: +98 361 591 2397.
E-mail address: Safari@kashanu.ac.ir (J. Safari).
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1381-1169/© 2014 Elsevier B.V. All rights reserved.
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2
O
O
H
NH2
NH
O
Metal-CNTs
M.W.
+
NH2
N
H
2
1
R
3
R
Scheme 1. Direct condensation of anthranilamide with aldehydes catalyzed by metal-CNTs under microwave irradiation.
particles/CNTs have unique properties with respect to the specific
particle morphology (size and shape), concentration, metal disper-
sion and the electronic properties of the metal on the CNTs surface
[32]. Additionally, metal NPs/CNTs nanocomposites have presented
attractive applications in many fields including sensors, catalysis,
fuel cells, electroanalysis and surface-enhanced Raman scattering
[33–37]. Several approaches have been developed to prepare CNT-
metal NPs assemblies involving electrochemical reduction [38,39],
the direct decoration of metal nanoparticles [40], spontaneous
reduction [41] and substrate-enhanced electrochemical reduction
[42]. However, the investigations have shown that the surface of
the CNTs is hydrophobic and highly inert because of high graphiti-
zation [43,44]. In order to active the surfaces of the tubes, surface
modification of CNTs has been done by using different acid treat-
ments to create carboxylic, carbonyl and hydroxyl groups [45]. The
presence of acidic groups makes CNTs surface more hydrophilic
[46] and enhances the affinity between the metal and carbon,
approving the incorporation of metallic nanoparticles and avoiding
agglomeration [47]. Therefore, conjunction of metal NPs with func-
tionalized CNTs increases the catalytic properties of metal, which
helps electron–hole pair separation and free migration of electrons
from the metal to the electron-accepting CNT surface [48].
We employed microwave energy because of the extensive appli-
cation of microwave technology in organic synthesis particularly
in solid state. Also, it accelerates unique chemical processes with
special attributes including reduced polluting, greater selectivity,
enhanced reaction rates and ease of manipulation [49]. Current
study has been employed as an alternative new methodology for
the synthesis of 2,3-dihydro-2-aryl-4(1H)-quinazolinones under
microwave irradiation. Herein, we would like to introduce some
metals supported on multi-walled carbon nanotubes as hetero-
geneous catalysts for the synthesis of quinazolinones. Therefore,
we have introduced the reaction of substituted aldehydes with
anthranilamide (2-aminobenzamide) as the source of nitrogen in
the presence of these catalytic systems (Scheme 1). The catalysts
are efficient, recyclable and easy to be separated from the reaction
mixture via simple filtration. The green and neat approach, easiness
and variability in derivatives in the present procedure makes it an
attractive method.
spectra were obtained in DMSO-d6 solution by a Bruker DRX
400 MHz spectrometer and chemical shifts are expressed in ı ppm
downfield from TMS as an internal standard. X-ray diffraction
(XRD) pattern of the as-synthesized material was carried out on a
Holland Philips Xpert X-ray diffraction (XRD) diffractometer (CuK,
radiation, ꢀ = 0.154056 nm and 40 kV voltage), at a scanning speed
of 2◦ min−1 from 10◦ to 100◦ (2ꢁ). The nanocomposites were char-
acterized using a KYKY scanning electron microscope (SEM) model
EM3200 operated at a 25 kV accelerating voltage. The TEM images
were recorded on a Zeiss EM10 C Transmission electron micro-
scope (TEM) operated at 80 kV accelerating voltage. The Raman
spectra were measured by a Bruker SENTERRA spectrometer with
spectral range: 200–3500 cm−1 and Laser wavenumber 785 nm.
2.1. General procedure for the preparation of quinazolinones
under microwave irradiations
Co-CNTs (0.025 g) were added to the mixture of benzaldehyde
(1 mmol) and 2-aminobenzamide (1 mmol) in a 25 mL pyrex flask
and microwave energy were irradiated under solvent free condi-
tion. The reactions were followed by thin layer chromatography
(TLC) using petroleum ether/ethyl acetate (7:3) as a mobile phase.
After completion, hot ethanol was added to the resulting mixture
and the heterogeneous catalyst was separated by filtration. Then,
the filtrate precipitated onto crushed ice while was being stirred for
several minutes. Insoluble products were filtered and recrystallized
from ethanol to afford the pure product.
3. Results and discussion
Interest in the environmental control of chemical processes
to provide an eco-friendly system has increased significantly in
recent years. The most important principles of the green chemistry
are the elimination of toxic and hazardous solvents in chemi-
cal synthesis, avoidance from the generation of waste and use of
environmentally friendly and recyclable catalyst. A solvent-free
or solid state reaction reduces pollution and cost and the formed
products are pure enough without the need to chromatography.
Therefore, it was interesting to investigate the catalytic effect of
a number of transition metals supported on CNTs in the synthe-
sis of the quinazolinone compounds under microwave irradiation
in solvent free conditions as a green media. To exploit environ-
mental friendly, facile and suitable conditions for the generation of
2-substituted 2,3-dihydroquinazolin-4(1H)-ones, the solvent free
treatment of substituted aldehydes and anthranilamide under
microwave irradiation was selected as a model reaction. From a
practical perspective, these catalysts can be easily prepared from
available reagents according to literature procedures [50–53] and
they can also be recycled. In addition, the functionalization process
can be carried out by pretreatment of CNTs in mixture of HNO3
and H2SO4 for surface modification of CNTs. The acidic sites using
improvement of the surface hydrophilicity can act as nucleation
2. Experimental
All materials and reagents were purchased from Merck Com-
pany. Melting points were recorded by Electrothermal MK3
apparatus using open capillaries and they are uncorrected.
MWCNTs were purchased from Nanotech Port Co. (Taiwan).
These MWCNTs were produced via the chemical vapor deposition
(CVD, or sometimes called catalytic pyrolysis) method. The outer
diameter of CNTs was between 10 and 20 nm. The progress of
the reactions and the purity of the products were monitored by
thin-layer chromatography (TLC). FT-IR spectra were obtained by
a Perkin Elmer FT-IR 550 spectrophotometer (KBr pellets). NMR
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Table 3
3
Table 1
Condensation of anthranilamide and benzaldehyde in presence of different catalysts.
Effect of irradiation power on the yield of dihydroquinazolinones.
Entry
Catalyst
Time (min)
Yield (%)
Entry
Power (W)
Time (min)
Yield (%)
1
2
3
4
Ag-CNTs
Co-CNTs
Cu-CNTs
Pt-CNTs
25
10
20
15
75
98
80
89
1
2
3
4
5
6
100
200
300
400
500
600
59
37
25
20
10
10
50
65
70
87
98
98
Table 2
Effects of different amounts of Co-CNTs nanocomposites on the model reaction.
Table 4
Entry
Catalyst (g)
Time (min)
Yield (%)
Reusability of Co-CNTs in the synthesis of 4a.
1
2
3
4
5
6
0
49
35
20
15
10
10
10
61
76
90
98
94
Run
1
2
3
4
5
0.01
0.015
0.02
0.025
0.03
Yield (%)
98
97
97
95
95
adsorption of the corresponding product in the excess active sites
and restricted dispersion of the adsorbed product within the active
sites of the catalytic system.
center for the deposition of metal NPs on the surface of CNTs. Our
initial study was started by employing a number of nanocompos-
ites such as Ag-CNTs, Co-CNTs, Cu-CNTs and Pt-CNTs to evaluate
the capability and efficiency of their catalytic activity and to pro-
mote the model condensation reaction. As Table 1 shows, initial
screening studies identified that all the above-mentioned catalysts
show a good catalytic activity for the model reaction but Co-CNTs
exhibited the highest catalytic activity as compared with other
catalysts in terms of time, yield and reaction conditions. Catalytic
activity of these nanocomposites decreases in the following order:
Co-CNTs > Pt-CNTs > Cu-CNTs > Ag-CNTs. The advantage of the Co-
CNTs for this reaction is the more number of unfilled d-orbitals of
the metal particles, its better Lewis acid character, greater selectiv-
ity and more stability. With notice to these results, Co-CNTs were
chosen as the best catalyst for further work.
During the present synthesis, the effect of amount of catalyst
in yield and reaction time was evaluated. Table 2 shows that the
yields of 2-aryl-2,3-dihydroquinazolin-4(1H)-one were improved
initially with increase in the amount of catalyst at short reaction
times. The optimum amount of catalyst was found to be 0.025 g
with respect to product yield, reaction time and concentration of
catalyst. The use of excessive amounts of the catalyst can increase
The rapid microwave-assisted organic synthesis (MAOS) of
quinazolinones under solvent-free conditions results shorten reac-
tion times, improved reaction yields and easier work up in
agreement with green chemistry protocols. It is noticed that the
synergetic effects of MW/nanocomposites couple have promoted
this solvent free condensation. Also, the effect of irradiation power
on the reaction progress was studied. As shown in Table 3, it was
observed that the yield and reaction time were significantly influ-
enced by irradiation power. Increasing the power to 500 W led to
the reduction of reaction time and improvement of the yield of
products. A further increasing in power did not increase the product
yield.
The use of heterogeneous and reusable catalysts represents one
of the greenest procedures in chemical technology. Moreover, het-
erogeneous catalysts should not only be stable and active, but also
require easy separating and reusing for useful applications. For this
purpose, hot ethanol was added to the mixture reaction and the
solid catalyst separated by filtration, was washed in ethyl acetate
and dried at 100 ◦C for 1 h, and finally was reused for the same
reaction process. It is noteworthy to highlight that catalyst could
be recovered efficiently and could be recycled while no decrease in
Table 5
Cobalt supported on CNTs promoted synthesis of substituted dihydroquinazolinones under microwave irradiation.
Entry
R
Product
Time (min)
Yield (%)
M.p (◦C)
Found
Reported
1
2
3
4
5
6
7
8
H
4-OH
3-NO2
2,4-(OMe)2
4-OMe
4-Cl
4-Me
4-CN
3-F
2-Naphthyl
2-Br
2-Cl
2-OH
2,4-Cl2
4-F
4-(NMe2)
4-Br
2-NO2
2,3-Cl2
3-Cl
2-OMe
2,3-(OMe)2
2-F
3a
3b
3c
3d
3e
3f
3g
3h
3i
3j
3k
3l
3m
3n
3o
3p
3q
3r
10
35
10
25
20
15
30
10
10
20
15
10
35
15
10
30
10
10
20
15
20
30
10
98
77
95
81
82
89
86
93
96
84
88
90
75
85
89
78
86
91
84
87
80
78
90
216–218
279–280
196–198
184–186
181–183
205–206
225–227
250–252
264–266
225–226
172–173
204–205
222–224
167–169
203–204
208–210
195–197
193–194
223–225
185–187
173–174
239–241
265–267
217–219 [54]
278–280 [55]
195–196 [54]
186–187 [55]
182–184 [56]
206–207 [54]
224–226 [54]
249–251 [57]
266–267 [55]
225–227 [58]
173–175 [59]
203–205 [56]
221–223 [60]
165–167 [56]
203–205 [61]
210–212 [54]
197–199 [62]
190–192 [60]
225–227 [63]
186–188 [64]
173–175 [64]
238–240 [65]
266–267 [66]
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
3s
3t
3u
3v
3w
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Fig. 1. The scanning electron microscope (SEM) micrographs of the (a) Co-CNTs, (b) Pt-CNTs, (c) Ag-CNTs and (d) Cu-CNTs.
Fig. 2. Images of the TEM of Co nanoparticles supported on carbon nanotubes.
Fig. 3. FT-IR of (a) acid treatment CNTs and (b) Co-CNTs.
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the presence of several metal-CNTs as novel green promoters
under microwave irradiation. Therefore, we have investigated the
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Acknowledgment
The authors would like to thank the University of Kashan for
financial support of this work by Grant No. 256722/28.
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