Synthesis of quinazolines over recyclable Fe3O4@SiO2-PrNH2-Fe3+ nanoparticles: A green, efficient, and solvent-free protocol

Article abstract of DOI:10.1002/aoc.4573

A practical and efficient method is developed for efficient synthesis of quinazoline derivatives through condensation reaction of 2-aminoaryl ketone, an aldehyde, and ammonium acetate, over magnetic Fe₃O₄@SiO₂-PrNH₂

Full text of DOI:10.1002/aoc.4573

Received: 15 June 2018
DOI: 10.1002/aoc.4573
Revised: 3 August 2018
Accepted: 4 August 2018
F U L L P A P E R
Synthesis of quinazolines over recyclable
3
+
Fe O @SiO ‐PrNH ‐Fe nanoparticles: A green, efficient,
3
4
2
2
and solvent‐free protocol
1
1
2
Esmaiel Eidi | Mohamad Z. Kassaee
| Zahra Nasresfahani | Peter T. Cummings
1
Department of Chemistry, Tarbiat
A practical and efficient method is developed for efficient synthesis of
quinazoline derivatives through condensation reaction of 2‐aminoaryl ketone,
an aldehyde, and ammonium acetate, over magnetic Fe O @SiO ‐PrNH ‐
Modares University, P.O. Box 14155‐175,
Tehran, Iran
2
Chemical and Biomolecular Engineering,
3
4
2
2
Vanderbilt University, Nashville, TN
3+
Fe NPs as a recyclable nanocatalyst, under solvent‐free conditions. The as‐
prepared nanocatalyst was characterized using Fourier transform infrared
spectroscopy (FT‐IR), X‐ray diffraction (XRD), field emission scanning electron
microscopy (FE‐SEM), transmission electron microscopy (TEM), thermogravi-
metric analysis (TGA), and vibrating sample magnetometer (VSM). Mild
conditions, easy work up, high purity of the products, recyclability, readily
availability, nontoxicity, economical, and environmental‐friendly nature of
the iron catalyst are the attractive features of this methodology.
3
7240, USA
Correspondence
Mohamad Z. Kassaee, Visiting Scholar,
Department of Chemistry, Tarbiat
Modares University, P.O.Box 14155‐175,
Tehran, Iran.
Email: mohamad.z.kassaee@vanderbilt.edu;
kassaeem@modares.ac.ir
KEYWORDS
Iron catalyst, Magnetic nanoparticles, Quinazoline, Recyclable, Solvent‐free
1
| INTRODUCTION
Especially as catalyst, MNPs have attracted considerable
attention because of their easy separation from the
One of the most important nitrogen heterocycles found
in a wide variety of natural products is quinazoline. It
has received great attentions in organic synthesis and
mother solution by magnetic decantation rather than
[
28]
time‐consuming filtration.
The immobilization of cata-
lytically active metal complexes on MNPs offers the
advantages of a combination of high catalytic activity,
selectivity and stability with easier separation of the cata-
lysts from the reaction media, thus makes it a reusable
and efficient system. In this context, some of MNPs have
been coated with amorphous type silica which acts as a
[1–5]
medicinal chemistry.
Many of its derivatives exhibit
a broad range of remarkable biological and pharmaco-
[
6]
[7]
logical activities such as antimalerial, antibacterial,
[8]
[9]
[10]
antiasthmatic,
antiinflammatory,
antihypertensive,
anticancer,
antiviral,
etc. Others are
[11]
[4,12]
[
13–16]
building blocks for naturally occurring alkaloids,
stabilizer and improves their chemical stability and
[17]
[29,30]
microorganisms
as gefitinib (Iressa)
Scheme 1).
Therefore, the design of new strategy for synthesis of
and in several life‐saving drugs such
dispersibility.
Silica‐coated MNPs have appeared as
[5,18]
[19]
and erlotinib (Tarceva)
versatile supports for the immobilization of metal
complexes. Among transition metal catalysts, the readily
available iron complexes have found increasing
applications, as environmentally benign, economical,
(
quinazolinones has attracted many researchers. Recently,
there has been exponential growth in creating magnetic
nanoparticles (MNPs) and led to their potential
applications in some fields such as biomedicine, catalysis,
[
31]
and nontoxic efficient catalysts in hydrogenation,
oxi-
[
32]
[33]
dation,
epoxidation,
etc. Herein, we have combined
two complementary properties, high reactivity and
[
20–27]
3+
environmental protection, and energy storage.
stability of the catalyst by immobilization of Fe on
Appl Organometal Chem. 2018;e4573.
wileyonlinelibrary.com/journal/aoc
© 2018 John Wiley & Sons, Ltd.
1 of 9
https://doi.org/10.1002/aoc.4573

2
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EIDI ET AL.
O
N
Me
N
N
O
N
HN
N
MeO
Rutaecarpine
NH
F
2
H N
N
Vandetanib
H
N
N
OMe
OMe
Br
O
O
N
NH2 Me
MeO
MeO
Trimetrexate
N
OMe
F
NH
Tarceva
N
N
Me
N
N
H2N
MeO
N
O
Afloqualone
N
N
O
O
Cl
NH
O
Iressa
N
F
MeO
MeO
N
N
O
CO2H
HO2C
N
N
O
Prazosin
NH2
O
S
Me
Proquazone Me
N
O
HN
Me
N
Me
Me
N
Raltitrexed
SCHEME 1 Occurrence of quinazolines in some important biological and pharmacological compounds
MNPs and its employment as a reusable heterogeneous
catalyst for the synthesis of quinazoline derivatives via a
one‐pot three‐component reaction of 2‐aminoaryl
ketones, aldehydes, and ammonium acetate, under eco‐
friendly solvent‐free conditions (Scheme 2).
was recorded at room temperature using a Philips X‐Pert
1710 diffractometer with Co Kα (α = 1.79285 Å) voltage
of 40 kV, current of 40 mA, in the range of 20°–80° (2θ)
with a scan speed of 0.02°/s. TGA thermogravimetric
analyzer was used to study the thermal properties of the
compounds under an inert N atmosphere and heating
2
−
1
rate of 10 °C min . An energy dispersive detector (EDS)
coupled to the microscope was used to identify chemical
elements of the prepared catalyst. The particle morphol-
ogy was examined by scanning electron microscopy using
SEM (HITACHI S‐4160) on gold coated samples and TEM
(Zeiss ‐ EM10C ‐ 100 KV). Magnetic properties were
obtained by a vibrating magnetometer/Alternating Gradi-
ent Force Magnetometer (VSM/AGFM, MDK Co., Iran).
2
2
| Experimental
.1 | Materials and physical techniques
All chemical reagents used in our experiments were pur-
chased from Merck or Aldrich Chemical Company with
high purity. All solvents were distilled, dried and purified
using standard procedures. Thin layer chromatography
(TLC) was performed using aluminium plates coated with
silica gel 60 F‐254 (Merck). Melting points were measured
2
3
.2 | Preparation of magnetic Fe O4
1
13
on an Electro‐thermal 9100 apparatus. H NMR and
NMR spectra were recorded on a Bruker Avance (DPX
00 MHz and DPX 125 MHz) in pure deuterated CDCl3
C
magnetic nanoparticles (MNPs)
5
Magnetic nanoparticles were prepared via chemical co‐
precipitation using chlorine salts of Fe and Fe ions
with molar ratio of 2:1, in the presence of NH OH,
followed by the hydrothermal treatment. Typically,
FeCl ·6H O (1.76 g, 0.0065 mol) and FeCl ·4H O
3+
2+
solvent using tetramethylsilane (TMS) as an internal ref-
erence. Fourier transform infrared (FT‐IR) spectra were
recorded using KBr pellets on a Nicolet IR‐100 infrared
spectrometer. The powder X‐ray diffraction spectrum
4
3
2
2
2
Ph
O
Ph
R
R
N
H
O
3+
Fe3O4@SiO2-PrNH2- Fe
o
Solvent-free, 60 C
SCHEME 2 Catalytic synthesis of
+
+
NH4OAc
N
NH2
R
3 4 2
quinazoline derivatives over Fe O @SiO ‐
R
3+
2
PrNH ‐Fe

EIDI ET AL.
3 of 9
(
0.65 g, 0.0033 mol), were dissolved in 100ml of deionized
and refluxing for 24 hr under N2 atmosphere. The
product was separated by an external magnetic, washed
with toluene and anhydrous ethanol, and dried under
vacuum for 24 hr at 60 °C.
water and vigorously stirred under Ar atmosphere for 1 h.
Then 6ml of 25% NH OH was dropped into the reaction
mixture. The reaction was continued for another 60 min
at 80°C, the cooled mixture was separated by an external
magnet, washed with distilled water, and dried overnight
under vacuum at 50 °C.
4
2
.5 | Preparation of iron (III) Schiff base
grafted onto Fe O @SiO ‐PrNH
3
4
2
2
1
g Fe O @SiO ‐PrNH was sonicated in dry dichloro-
3
4
2
2
2
.3 | Preparation of silica coated magnetic
methane (25 ml), then an aqueous solution of Fe (acac)3
nanoparticles (Fe O @SiO )
3
4
2
(
100 mg in 10 ml) was added slowly into the above
Magnetic nanoparticles (1 g) was dispersed in a solution
of ethanol and water (40:10 ml) in an ultrasonic bath
for 30 min. The pH was adjusted to 10 with an ammonia
solution and 0.5 ml tetraethylorthosilicate (TEOS) that
was added drop‐wise into the mixture over a period of
mixture and refluxed for 24 hr. After cooling to room
temperature, the mixture was separated by an external
magnet, washed with copious amounts of dichlorometh-
ane and ethanol to remove the ungrafted Fe (acac) .
3
3+
Finally, Fe O @SiO ‐PrNH ‐Fe
was dried under
3
4
2
2
1
0 min. Then, the mixture was stirred using a mechanical
stirrer for 12 hr at 60 °C. The obtained Fe O @SiO
2
vacuum at 60 °C for 12 hr.
3
4
nanoparticles were collected using an external magnet,
subsequently washed with ethanol several times and
dried under vacuum.
2
.6 | General procedure for the synthesis
of quinolones
A mixture of 2‐aminoaryl ketone (1 mmol), aromatic
aldehyde (1 mmol), ammonium acetate (2.5 mmol) and
catalyst (10 mg) was placed in a round bottom flask and
heated in an oil bath at 60 °C. After completion of the
reaction which was indicated by TLC, ethanol (5 ml)
was added to the reaction mixture, the catalyst was
separated using an external magnet, washed several times
with water and ethanol and dried under vacuum at room
temperature to be ready for the next run. Then, solvent
2
.4 | Preparation of amino‐functionalized
magnetic nanoparticles (Fe O @SiO ‐
PrNH )
3
4
2
2
The surface of the silica coated magnetic
nanoparticles was functionalized with amino groups by
adding 3‐aminpropyltriethoxysilane (APTES) (1 ml) to a
suspension of Fe O @SiO (1 g) in dry toluene (25 ml)
3
4
2
3
+
3 4 2 2
SCHEME 3 Preparation of magnetic nanocatalyst Fe O @SiO ‐PrNH ‐Fe
3
+
3 4 2 3 4 2 2 3 4 2 2
FIGURE 1 FT‐IR spectra of: (a) Fe O @SiO , (b) Fe O @SiO –PrNH , (c) Fe O @SiO ‐PrNH ‐Fe

4
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EIDI ET AL.
was evaporated under reduced pressure. To afford pure
quinazoline derivatives, the solid residue was recrystal-
lized from ethanol.
immobilization of the metal complex on the
Fe O @SiO –PrNH surface, increasing the intensity of
3
4
2
2
the C―H stretching vibration can indirectly suggest that
metal acetylacetonate has been successfully grafted onto
the modified Fe O (Figure 1c).
3
4
3
| RESULTS AND DISCUSSION
In this section, we discuss the preparation, characteriza-
3+
tion and application of Fe O @SiO ‐PrNH ‐Fe as an
3
4
2
2
efficient, eco‐friendly and reusable heterogeneous
nanocatalyst for the synthesis of quinazoline derivatives.
The magnetic system is prepared in three steps
(Scheme 3). Then, characterization of catalyst is done
via FT‐IR, SEM, TEM, VSM, TGA/DTA and XRD.
The FT‐IR spectra of Fe O @SiO , Fe O @SiO –
3
4
2
3
4
2
3
+
PrNH , and Fe O @SiO ‐PrNH ‐Fe in Figure 1 show
2
3
4
2
2
−
1
an adsorption peak at around 565 cm that is attributed
to the vibration of Fe–O bonds and the bands at 450,
−
1
1
075, 1618 and 3430 cm which show silica has coated
as a shell on surface of Fe O . The presences of bands
3
4
−
1
in the 2925–2858 cm
region in spectra of
Fe O @SiO –PrNH are assigned to the stretching of
3
4
2
2
−
1
C―H bonds. Moreover, the band at 1558 cm is due to
the bending vibrations of H―N―H bond; however
absorption bands of the stretching vibration of –NH are
2
overlapped with the–OH stretching vibration. Thus, it
can be confirmed that surface modification of the silica
shell by APTES is successful (Figure 1b). After
FIGURE 2 Wide‐angle XRD patterns of (a) Fe
3
O
4
and (b)
3 4 2 2
FIGURE 3 Images of: (a) SEM, (b) TEM of Fe O @SiO ‐PrNH ‐
Fe and (c) TEM of recycled catalyst after last run
3
+
3+
Fe
3
O
4
@SiO
2
‐PrNH
2
‐Fe catalyst

EIDI ET AL.
5 of 9
The properties of crystallinity and phase purity of
room temperature, in the range from +1 to −1 T. The
magnetization hysteresis loops of them are S‐like curves
3+
the as‐synthesized Fe O and Fe O @SiO ‐PrNH ‐Fe
3
4
3
4
2
2
are investigated by wide angle XRD. For Fe O @SiO ‐
that indicate they are super paramagnetic (Figure 5).
3
4
2
3+
−1
PrNH ‐Fe NPs, XRD pattern are in agreement with
The magnetic saturation (M ) values are 24.0 emu g
2
sat
−
1
3+
standard patterns of inverse cubic spinel magnetite
and 68.0 emu g
for Fe O @SiO ‐PrNH ‐Fe
and
3
4
2
2
(
Fe O ) crystal structure, showing six diffraction peaks
Fe O , respectively. The decrease in Msat for
3 4
3 4
3+
at 2θ about 35.1°, 41.5°, 50.5°, 63.1°, 67.3° and 74.3°
Fe O @SiO ‐PrNH ‐Fe can be attributed to the modifi-
3
4
2
2
corresponding to the respective (220), (311), (400),
cation on the surface of the Fe O with nonmagnetic
3 4
3+
(422), (511), and (440) planes, respectively (Figure 2).
material [PrNH ‐Fe ]. These properties cause to facili-
2
Sharp peaks confirm the good crystallinity of the
prepared samples. The small and weak broad bands in
around 25 is related to the existence of amorphous silica
shell.
tate separation of magnetic nanoparticles with a conven-
tional magnet which is efficient for recovery of the
catalyst.
The size and morphology of the Fe O @SiO ‐PrNH ‐
3
4
2
2
3+
Fe NPs are determined via SEM and TEM analyses.
In SEM image, particles with uniformly spherical
morphology are observed. TEM image shows Fe O nano-
3
4
particles covered with organic and inorganic groups
Figure 3).
Thermal stability of Fe O @SiO ‐PrNH ‐Fe
(
3+
is
3
4
2
2
obtained from the thermogravimetric (TG) and differen-
tial thermal analysis (DTA), under an air flow from room
−
1
temperature to 800 °C at a rate of 10 °Cmin . In TGA
diagram, the first weight loss below 200°C is due to phys-
ically adsorbed water and solvents. This was followed by
a gradual decrease in the weight between 200 °C and
6
50 °C which is attributed to the decomposition of the
grafted organic molecule on the surface. These result
are indicate that the surface modification has occurred
(
Figure 4).
3+
The magnetic properties of the as‐synthesized Fe O
FIGURE 5 VSM curve of Fe O NPs, Fe O @SiO ‐PrNH ‐Fe
NPs and recycled catalyst after last run
3
4
3
4
3
4
2
2
3+
and Fe O @SiO ‐PrNH ‐Fe are measured by VSM at
3
4
2
2
3
+
3 4 2 2
FIGURE 4 TGA/DTA/DTG analysis of Fe O @SiO ‐PrNH ‐Fe

6
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EIDI ET AL.
TABLE 1 Optimization of the catalytic synthesis of quinazoline
derivatives over Fe O @SiO ‐PrNH ‐Fe
3 4 2 2
4
| CATALYST ACTIVITY
3
+a
3
+
b
Catalytic activity of Fe O @SiO ‐PrNH ‐Fe is probed
Catalyst
(mg)
Time
(h)
Yield
(%)
3
4
2
2
o
Entry
Solvent
T/ C
through synthesis of quinazoline derivatives in a three
component condensation reaction of 2‐aminoaryl
ketones, aldehydes, and ammonium acetate. Firstly, to
optimize conditions, model reaction is performed by
using 2‐aminobenzophenone, benzaldehyde, and ammo-
nium acetate. Effects of different amounts of the catalyst,
time and temperature of the reaction, as well as the
solvent effects are explored on the overall yield of the
reaction. In the absence of the catalyst, reaction yield in
low, while in its presence (10 mg) the yield of the product
increases at 40 °C. However, an amount higher than
10 mg does not improve the yield to an appreciable extent
at this temperature. It is found that the yield improves to
1
2
3
4
5
6
7
8
9
10
10
15
10
10
15
10
10
10
10
10
‐
‐
‐
‐
‐
‐
‐
25
40
40
40
60
60
60
80
60
70
60
60
5
4
4
5
4
4
4
4
4
4
4
4
37
70
73
75
95
95
68
80
84
89
39
H
H
2
2
O
O
EtOH
EtOH
10
11
12
9
5% at 60 °C and in solvent‐free conditions. The effect of
solvent is investigated for the model reaction using H O,
EtOH, and CH CN. The results show that conducting
3
CH CN
2
‐
Trace
3
a
Reaction conditions: 2‐aminobenzophenone (1 mmol), benzaldehyde
1 mmol), ammonium acetate (2.5 mmol).
the reaction under solvent‐free condition generates the
desired product in an excellent yield. Based on these
results, the optimal conditions are determined as that
(
b
Isolated yield.
3
+
a,b
3 4 2 2
TABLE 2 Synthesis of quinazoline derivatives over Fe O @SiO ‐PrNH ‐Fe under solvent‐free condition
a
Reaction conditions: 2‐aminoaryl ketone (1 mmol), aldehyde (1 mmol), ammonium acetate (2.5 mmol). 60 °C, 4 hr.
b
Isolated yield.

EIDI ET AL.
7 of 9
FIGURE 6 Recyclability of
3+
3 4 2 2
Fe O @SiO ‐PrNH ‐Fe NPs in catalytic
synthesis of quinazolines
SCHEME 4 A proposed mechanism for
the synthesis of quinazolines over
3+
3 4 2 2
Fe O @SiO ‐PrNH ‐Fe NPs
the reaction is catalyzed by 10 mg of catalyst under
solvent‐free conditions at 60 °C (Table 1).
noteworthy that no significant change in the activity are
observed for least 4 consecutive cycles which clearly
demonstrates the stability and durability of the catalyst
(Figure 6).
In order to further demonstrate the utility of this
methodology, we extend our studies with a wide range
of aldehydes. It can be clearly observed that electronic
and steric effects of substitutions on the aldehyde do not
appreciably affect the yield of the desired product.
Moreover, the reaction is well tolerated with other func-
tional group halide (Cl) substituent on the substrates of
A
possible mechanism for the synthesis of
3+
quinazolines over Fe O @SiO ‐PrNH ‐Fe NPs is pre-
sented (Scheme 4). The Fe O @SiO ‐PrNH ‐Fe NPs
3
4
2
2
3
+
3
4
2
2
acts as a Lewis acid, coordinates to the carbonyl groups
and increases the electrophilicity of the carbonyl groups
of 2‐aminoaryl ketones and aldehydes. In the first step,
the nucleophilic attack of the amine's substrate (1) on
the activated carbonyl group of aldehyde (2), leads to an
aldimine intermediate A. In the next step, condensation
of the keto group of benzophenone in intermediate A
2‐aminobenzophenone (Table 2).
Facility of catalyst recovery is very important parame-
ter in performance of catalytic system. To obtain an
insight into this issue, catalyst reusability experiments
are carried out under the same reaction conditions. After
3+
the reaction is completed, Fe O @SiO ‐PrNH ‐Fe is
with NH OAc (3), forms ketimine group in intermediate
3
4
2
2
4
easily separated with an external magnet from the
reaction solution, the recovered catalyst is washed with
ethanol, then dried and used in the next run. It is
B. Then, the intermediate C is obtained via cyclization
and transformation of hydrogen, which may render
desired product (4) through aerial oxidation.

8
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EIDI ET AL.
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| CONCLUSION
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Along this research line, we have developed a simple,
inexpensive and robust protocol to immobilize iron on
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heterogeneous catalyst for the synthesis of quinazoline
derivatives via a one‐pot three‐component reaction of 2‐
aminoaryl ketones, aldehydes, and ammonium acetate
under eco‐friendly conditions. The advantages of this pro-
tocol includes avoiding the use of solvent, high yields,
easy handling, short reaction time, simple experimental,
and product purity. These together with the simple
recovering of the catalyst make it a useful alternative for
the scale‐up for the synthesis of quinazoline derivatives.
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How to cite this article: Eidi E, Kassaee MZ,
Nasresfahani Z, Cummings PT. Synthesis of
quinazolines over recyclable Fe O @SiO ‐PrNH ‐
Fe nanoparticles: A green, efficient, and solvent‐
free protocol. Appl Organometal Chem. 2018;e4573.
https://doi.org/10.1002/aoc.4573
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