Sonosynthesis of furan-2(5H)-ones using nanosilica-tethered polyhedral oligomeric silsesquioxanes

Article abstract of DOI:10.1007/s13738-019-01711-5

Abstract: An easy and rapid method for the synthesis of 3,4,5-substituted furan-2 (5H)-ones has been achieved through a three-component reaction of aniline, dialkyl acetylenedicarboxylate, and aromatic aldehydes using nanosilica-tethered polyhedral oligom

Full text of DOI:10.1007/s13738-019-01711-5

Journal of the Iranian Chemical Society
https://doi.org/10.1007/s13738-019-01711-5
ORIGINAL PAPER
Sonosynthesis of furan‑2(5H)‑ones using nanosilica‑tethered
polyhedral oligomeric silsesquioxanes
Hossein Shahbazi‑Alavi1 · Sheida Khojasteh‑Khosro2 · Javad Safaei‑Ghomi2 · Seyed Hadi Nazemzadeh2
Received: 27 November 2017 / Accepted: 7 June 2019
© Iranian Chemical Society 2019
Abstract
An easy and rapid method for the synthesis of 3,4,5-substituted furan-2 (5H)-ones has been achieved through a three-
component reaction of aniline, dialkyl acetylenedicarboxylate, and aromatic aldehydes using nanosilica-tethered polyhedral
oligomeric silsesquioxanes with eight branches of 3-aminopropyltriethoxysilane as catalyst under ultrasonic irradiations.
We reported a class of organic–inorganic hybrid material based on nanosilica-tethered polyhedral oligomeric silsesquiox-
anes with eight branches of 3-aminopropyltriethoxysilane (nanosilica @APTPOSS). The catalyst has been characterized
by proton nuclear magnetic resonance (1H NMR), scanning electronic microscopy, energy dispersive X-ray, DLS (dynamic
light scattering), and thermal gravimetric analysis. The high efciency, short reaction times, simple workup, reusability of
the catalyst up to six runs without considerable loss of activity, using the sonochemical procedure as green process, and an
alternative energy source are some benefts of this method.
* Hossein Shahbazi-Alavi
hosseinshahbazi99@yahoo.com
1
Young Researchers and Elite Club, Kashan Branch, Islamic
Azad University, Kashan, Iran
2
Department of Organic Chemistry, Faculty of Chemistry,
University of Kashan, Kashan 51167, Iran
Vol.:(0123456789)
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Journal of the Iranian Chemical Society
Graphic abstract
Keywords Organic–inorganic hybrid · Nanocatalyst · Furan-2 (5H)-ones · Ultrasonic conditions · One-pot
inorganic core of oxygen and silicon has size ~0.45 nm in
Introduction
diameter [13, 14]. In continuation of our works on synthesis
of nanoparticles [15–18], a series of polyhedral oligomeric
silsesquioxanes with eight branches of 3-aminopropyltri-
ethoxysilane (APTPOSS) has been anchored on the surface
of colloidal silica nanoparticles. In the current study, we
investigated an easy and rapid method for the synthesis of
3,4,5-substituted furan-2 (5H)-ones through a three-com-
ponent reaction of aniline, dialkyl acetylenedicarboxylate,
and aromatic aldehydes using nanosilica-tethered polyhedral
oligomeric silsesquioxanes with eight branches of 3-ami-
nopropyltriethoxysilane as catalyst under ultrasonic irradia-
tions (Scheme 1). Recently, several nanocatalysts have been
utilized for the preparation of organic compounds under
ultrasonic conditions [19, 20]. The ultrasound approach
decreases times and increases yields of products by creat-
ing the activation energy in microsurroundings [21, 22].
Cavitation process generates high temperature and pressure
in the microsurroundings which causes a disturbed current
in the liquid and elevated mass transfer [23, 24]. Compared
Furan-2(5H)-ones represent biological properties such
as anti-cancer [1], antimicrobial [2], antifungal [3], anti-
ulcer [4], and anti-HIV [5]. Hence, seeking easy and
brief techniques for the preparation of Furan-2(5H)-
ones is a signifcant subject. Recently, reports have been
developed on synthesis of furan-2 (5H)-ones using
the catalysts such as cyclodextrin [6], Al(HSO4)3 [7],
(CH3CH2CH2CH2)4N(HSO4) [8], HCOOH [9], Maltose
[10], SnCl2 [11], and Vitamin B12 [12]. Despite the use of
these ways, there remains adequate purpose to ofer a new
way for an efcient method to achieve such systems. The
use of highly efcient, economic, and retrievable catalysts,
with low or nil toxicity, is required from the green chemis-
try viewpoint. The surface of nanoparticles (NPs) can be
modifed through loading by desirable functionalities such as
polyhedral oligomeric silsesquioxanes (POSS). Silsesquiox-
ane is an organosilicon compound with the chemical formula
[RSiO3/2]n (R=H, alkyl, vinyl, aryl, alkoxy), including of an
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Journal of the Iranian Chemical Society
Scheme 1 Synthesis of
3,4,5-substituted furan-2(5H)-
ones under ultrasound irradia-
tions
O
CO2R
C
C
catalyst
EtOH
O
RO
Ar
NHC6H5
O
+
C6H5NH2
+
Ar
H
US (40 W)
O
CO2R
1
3
4
2
R = CH3 , C2H5
O
O
O
H
N
O
Si
Si
N
H
Si
O Si
O
O
H
N
O
O
O
O
O
O
O
Si
O
Si
N
H
Si
O
O
O
Si
Si
Si
H
N
Si
O
Si
SiO2
O
Si
Si
Si
O
O
SiO2
O
O
H
O
Si
N
O
H
N
O
N
Si
O
H
O
O
O
O
O
O
Si
cat.
to conventional heating which creates thermal energy in
the macrosystem, ultrasound irradiation is able to activate
numerous reactions by the activation energy in microenvi-
ronment [25].
2953, 1439, 1104,810. 1H NMR (400 MHz, CDCl3; δ, ppm):
0.81 (m, 2H), 1.88 (m, 2H), 3.54 (m, 2H).
Preparation of octakis[3‑(3‑aminopropyltrieth
oxysilane)propyl]octasilsesquioxane (APTPOSS)
Experimental
Firstly, 2 mmol (2.07 g) of Cl-POSS was added in 20 mmol
(4.43 g) of 3-aminopropyltriethoxysilane and was trans-
ferred to a round-bottom fask under N2 atmosphere. The
mixture was heated in an oil bath at 110 °C for 2 days. After
the reaction was complete, the mixture was cooled to room
temperature and the mixture was fltered and washed with
acetone and methanol to wash the additional reactants.
Finally, the resultant pale brown precipitates were dried in
a vacuum oven at 70 °C for 12 h (36% yield). Anal. Calcd
for C96H224N8O36Si16 (2516): C, 45.82; H, 8.97; N, 4.45.
Found: C, 45.56; H, 8.67; N, 4.32. IR (KBr; ν, cm−1): 2924,
1633, 1112, 1025.
All organic materials were purchased commercially from
Sigma-Aldrich and Merck and were used without further
purifcation. A multiwave ultrasonic generator (Sonicator
3200; Bandelin, MS 73, Germany), equipped with a con-
verter/transducer and titanium oscillator (horn), 12.5 mm
in diameter, operating at 20 kHz with a maximum power
output of 200 W, was used for the ultrasonic irradiation.
The ultrasonic generator automatically adjusted the power
level. CHN compositions were measured by Carlo ERBA
Model EA 1108 analyzer. The thermogravimetric analysis
(TGA) curves are recorded using a V5.1A DUPONT 2000.
To investigate the morphology and particle size of the syn-
thesis structures, NPs, FE-SEM images, and EDS spectrum
of the products were visualized by a Sigma ZEISS, Oxford
Instruments Field Emission Scanning Electron Microscope.
Preparation of nanosilica @APTPOSS
In a typical procedure, 0.3 mL of colloidal silica nanopar-
ticles (LUDOX SM colloidal silica 30 wt.% suspensions in
H2O) was diluted in 2 mL of deionized water. After that
0.6 g (0.24 mmol) of APTPOSS was dispersed in 3 mL of
deionized water by ultrasonic vibration for 15 min. Then,
the suspension was added slowly during 1h to above solu-
tion. The mixture was kept at 80 °C for one day (Scheme 2).
Finally, the nano-colloidal silica-attached APTPOSS was
separated by centrifugation and washed with acetone and
ethanol for several times, and then, the mixture was dried in
vacuum at 50 °C (28% yield) [26, 27].
Preparation of octakis(3‑chloropropyl)
octasilsesquioxane (Cl‑POSS)
3-Chloropropyltrimethoxysilane (80 g, 0.403 mol) was
added to a stirred mixture of methanol (1800 mL) and con-
centrated hydrochloric acid (90 mL). The reaction mixture
was stirred for 5 weeks at room temperature. Then, the
resultant solution was fltered and dried to give a white solid
in 42% yield. Anal. Calcd for Si8O12C24H48Cl8 (1036.9): C,
27.80; H, 4.67. Found: C, 27.74; H, 4.60. IR (KBr; ν, cm−1):
1 3

Journal of the Iranian Chemical Society
e
OM
Scheme 2 Preparation of nano-
e
e
OM
colloidal silica @APTPOSS
Cl
Si
OM
e
M
5
OH HCl
,
wee
k
Cl
Cl
Si
O
Si
O
Si
O
Cl
t
OE
O
O
O
Cl
Si
Si
O
Si
t
OE
O
S
i
+
O
H2N
S
i
O
O
Si
O
OEt
Cl
Cl
C
l
Cl
110 o
C
,
a
2 d
y
un er
d
N2
APTPOSS
EtO OEt
Et
t
OE
EtO
EtO
H
N
i
O
S
Si
N
H
EtO
Si
t
OE
Si
O
Si
O
Si
O
S
i
N
H
EtO
O
Et
H
O
O
O
i
N
S
Si
Si
O
Si
EtO
EtO
O
O
O
O
O
Si
co o a s ca
ll id l ili
M
S
HN
+
NH
N
H
t
OE
EtO Si
Si
NH
O
Et
EtO
t
OE
t
OE
t
OE
80 o
C
,
a
1 d
y
Si
Si
EtO
EtO
t
OE
t
OE
EtO
H
N
O
O
O
O
O
Si
Si
N
H
Si OSi
O
H
N
O
O
O
O
O
Si
Si OSi
Si
O
O
N
H
O Si
H
S
i
O
O
O
SiO2
Si
O
i
O
Si
S O2
N
O
Si
H
Si
O
O
N
O
H
N
O
Si OSi
Si
H
O
O
N
O
O
O
Si
O
O
General procedure for the synthesis
of furan‑2(5H)‑ones
Spectra data of new compounds
Ethyl 2‑(4‑chlorophenyl)‑2,5‑dihydro‑5‑oxo‑4‑
A mixture of aldehyde (2 mmol), aniline (2 mmol),
dialkyl acetylenedicarboxylate (2 mmol), and 14 mg of
nano-colloidal silica@APTPOSS in ethanol (15 mL)
was sonicated at 40 W power for the appropriate times
(monitored by TLC). After completion of the reaction,
the reaction mixture was diluted in CH2Cl2; the catalyst
was isolated by simple filtration, and the heterogeneous
catalyst was recovered. The CH2Cl2 was evaporated, and
the solid separated out was filtered and was washed with
ethanol to get pure product.
(phenylamino)furan‑3‑carboxylate (4j)
White powder; m.p.: 181–184 °C; IR (KBr): ꢀ̄=3220, 2922,
1687, 1596, 1239, 11368 cm−1; 1H NMR (400 MHz, CDCl3):
δ=1.20 (t, 3 H, J=7.2 Hz, CH3), 4.05 (m, 2H, J=7.2 Hz,
OCH2), 5.73 (s, 1H, benzylic), 7.12–7.52 (m, 9H, ArH),
8.95 (br s, 1H, NH) ppm; 13C NMR (100 MHz, CDCl3):
δ=168.95 (COO), and 165.04 (COOCH2), 156.07 (C-NH
of aromatic), 137.85 (C-NH alkene), 135.22 (C of aromatic),
134.96 (C–Cl of aromatic), 133.22 (CH of aromatic), 129.16
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Journal of the Iranian Chemical Society
(CH of aromatic), 126.19 (CH of aromatic), 123.22 (C of
alkene), 122.54 (CH of aromatic), 114.48 (CH of aromatic),
60.92 (OCH2), 52.18 (CH of benzylic), 14.32 (CH3) ppm;
Anal. Calcd for C19H16ClNO4: C, 63.78; H, 4.51; N, 3.91;
Found: C, 63.70; H, 4.45; N, 3.84.
(–Si–CH2CH2CH2Cl) and signals at δ 1.88 ppm and 3.54
are, respectively, assigned to the resonance of the methylene
protons (–Si–CH2CH2CH2Cl) and (–Si–CH2CH2CH2Cl).
1
The H NMR reveals that Cl-POSS was successfully
prepared.
Figure 2 shows FE-SEM image of nano-colloidal silica @
APTPOSS (nanocatalyst). It is observed that the particles are
strongly aggregated and glued with very large and continu-
ous aggregates easily observed.
Ethyl 2,5‑dihydro‑2‑(4‑nitrophenyl)‑5‑oxo‑4‑(phenylamino)
furan‑3‑carboxylate (4k)
White powder; m.p.: 250–252 °C; IR (KBr): ̄ꢀ = 3305,
2927, 2843, 1722, 1665, 1508, 1339, 1225 cm−1; 1H NMR
(400 MHz, CDCl3): δ = 1.22 (t, 3 H, J = 7.2 Hz, CH3),
4.07 (m, 2H, J = 7.2 Hz, OCH2), 5.82 (s, 1H, benzylic),
7.22–8.32 (m, 9H, ArH), 9.12 (br s, 1H, NH) ppm; 13C NMR
(100 MHz, CDCl3): δ=165.2 (COO), and 163.2 (COOCH3),
155.4 (C-NH of aromatic), 144.2 (C-NO2 of aromatic),
142.1 (C-NH alkene), 134.1 (C of aromatic), 130.2 (CH of
aromatic), 129.0 (CH of aromatic), 127.10 (CH of aromatic),
124.75 (CH of aromatic), 120.72 (C of alkene), 113.9 (CH of
aromatic), 61.3 (OCH2), 52.1 (benzylic), 14.32 (CH3) ppm;
Anal. Calcd for C19H16N2O6: C, 61.95; H, 4.38; N, 7.61;
Found: C, 61.82; H, 4.20; N, 7.50.
Results and discussion
The preparation steps of nanosilica-tethered polyhedral
oligomeric silsesquioxanes with eight branches of 3-ami-
nopropyltriethoxysilane have been described in Scheme 2.
In the frst step, Cl-POSS was synthesized by the hydroly-
sis of 3-chloropropyltrimethoxysilane under acidic condi-
tions. Afterward, reaction of 3-aminopropyltriethoxysilane
(20 mmol) with Cl-POSS (2 mmol) yields APTPOSS (36%
yield). Then, reaction of nanosilica with APTPOSS aforded
nanosilica @APTPOSS.
Fig. 2 FE-SEM image of nano-colloidal silica @APTPOSS
1
Figure 1 shows the H NMR spectra for the octakis(3-
chloropropyl)octasilsesquioxane (Cl-POSS) in CDCl3.
The NMR spectra of Cl-POSS are consistent with
expected results. The 1H NMR spectra of Cl-POSS display
a signal at δ 0.81 ppm due to the methylene protons
Fig. 3 Energy dispersive spectroscopy for APTPOSS and nano-col-
Fig. 1 1H NMR spectrum of Cl-POSS
loidal silica @APTPOSS
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Journal of the Iranian Chemical Society
We commenced our investigation by testing the reac-
tion of dimethyl acetylene dicarboxylate, aniline, and
4-chlorobenzaldehyde as model reaction for the synthesis
of furan-2 (5H)-ones. To obtain the ideal reaction condi-
tions for the synthesis of compound 4a, we studied the
diverse catalysts and solvents which are shown in Table 1.
Screening of diferent catalysts such as ZrOCl2·8H2O,
BF3·Et2O, nano-CeO2, nano-Fe3O4, APTPOSS, and
nano-colloidal silica@APTPOSS revealed nano-colloidal
silica@APTPOSS (14 mg) as the most efective catalyst to
perform this reaction under ultrasonic irradiation (40 W)
(Table 1). In this research, ultrasound irradiation is used
as green and complementary techniques for preparation
of furan-2 (5H)-ones. When the catalysis was performed
under ultrasound irradiations, the reaction rate increased
considerably. Longer reaction times were required under
conventional heating and assistance of ultrasound irradia-
tion did improve the yields of the reactions and shorten-
ing the reaction times. The possible explanation for the
positive association of irradiation is that the ultrasonic
irradiation could increase the number of active cavitation
bubbles and the size of the individual bubbles, both of
which are predictable to result in higher maximum col-
lapse temperature and accelerated respective reaction. We
explored the feasibility of the reaction by choosing some
representative substrates (Table 2). It has been considered
that better yields are achieved with substrates having elec-
tron-withdrawing groups. In addition, we examined isatin
instead of benzaldehydes in the reaction, but we could not
fnd considerable amount of the title product from isatin.
This reaction could not be observed when the isatins were
used as a substrate.
Fig. 4 TGA of nano-colloidal silica @APTPOSS
Fig. 5 DLS (dynamic light scattering) of nano-colloidal silica @
APTPOSS
We also checked reusability of nano-colloidal silica
@APTPOSS as an efcient catalyst; its reusability was
achieved by the reaction of dimethyl acetylene dicarboxy-
late, aniline, and 4-chlorobenzaldehyde and 14 mg of nano-
colloidal silica@APTPOSS under optimized conditions.
After completion of the reaction, the catalyst was washed
with water and acetone and was used with new substrates
under the same conditions. The results showed that the nano-
colloidal silica @APTPOSS can be reused several times
(yields 95 to 93%) in Fig. 6.
The components of the APTPOSS and silica @APTPOSS
were analyzed using EDS (Fig. 3). EDS confrmed the pres-
ence of C (45.70%), N (4.52%), O (22.90%), and Si (17.92%)
in APTPOSS, and the higher intensity of Si peak compared
with C peak in the nanocatalyst indicates SiO2 is loaded
with APTPOSS.
Thermogravimetric analysis (TGA) evaluates the thermal
stability of the nano-colloidal silica-tethered APTPOSS. The
curve shows a weight loss lower than 210 °C related to des-
orption of physically adsorbed water, while a weight loss
at the temperature from 210 to 560 °C could be due to the
decomposition of organic spacer attaching to the silica nano-
particles. Thus, the nanocatalyst was stable up to 210 °C
(Fig. 4).
A proposed mechanism for the formation of 4 is shown
in Scheme 3. An initial condensation of dimethyl acetylen-
edicarboxylate and aromatic amine generated intermediate
I. Subsequently, the reaction of aromatic aldehyde and inter-
mediate I and then cyclodehydration produced furan-2(5H)-
ones. In this mechanism, nano-colloidal silica @APTPOSS
acts as a highly efcient and green catalyst activating the
C=O, COO groups for better reaction with nucleophiles. It
is assumed that catalytically active site of catalyst contains
SiO2 that acts as a Lewis acid and APTPOSS (−NH−) that
acts as a Lewis basic.
In order to study the size distribution of nanocatalyst,
DLS (dynamic light scattering) measurements of the nano-
particles are shown in Fig. 5. The dispersion for DLS analy-
sis (2.5 g nanocatalyst at 50 mL ethanol) was prepared using
an ultrasonic bath (60 W) for 30 min.
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Journal of the Iranian Chemical Society
Table 1 Optimization of
reaction conditions using
diferent catalysts under
diferent conditionsa
Entry
Solvent (conditions)
Catalyst
Time (min)
Yieldd
%
1
2
3
4
5
6
7
8
EtOH (refux)
EtOH (refux)
CH3CN (refux)
DMF (refux)
EtOH (refux)
CH3CN (refux)
DMF (refux)
H2O (refux)
CH3CN (refux)
EtOH (refux)
No catalyst
ZrOCl2·8H2O (2 mol%)
BF3·Et2O (2 mol%)
Nano-CeO2 (4 mol%)
Nano-Fe3O4 (4 mol%)
APTPOSS (10 mol%)
Nano-colloidal silica@APTPOSS (14 mg)
Nano-colloidal silica@APTPOSS (14 mg)
Nano-colloidal silica@APTPOSS (14 mg)
Nano-colloidal silica@APTPOSS (14 mg)
Nano-colloidal silica@APTPOSSc (14 mg)
Nano-colloidal silica@APTPOSS (14 mg)
Nano-colloidal silica@APTPOSS (14 mg)
Nano-colloidal silica@APTPOSS (14 mg)
Nano-colloidal silica@APTPOSS (14 mg)
Nano-colloidal silica@APTPOSS (14 mg)
Nano-colloidal silica@APTPOSS (12 mg)
Nano-colloidal silica@APTPOSS (16 mg)
–
800
400
600
350
350
120
120
120
120
120
15
15
10
10
10
10
10
10
15
Trace
40
35
40
28
45
48
54
59
76
66
72
75
85
95
95
89
95
40
52
9
10
11
12
13
14
15
16
17
18
19
20
DMF (US: 40 W)b
H2O (US: 40 W)
CH3CN (US: 40 W)
EtOH (US: 30 W)
EtOH (US: 40 W)
EtOH (US: 50 W)
EtOH (US: 40 W)
EtOH (US: 40 W)
EtOH (US: 40 W)
EtOH (US: 40 W)
Nano-colloidal silica
10
a4-Chlorobenzaldehyde (2 mmol), aniline (2 mmol), dimethyl acetylenedicarboxylate (2 mmol)
bUltrasonic irradiation
cNano-colloidal silica@APTPOSS (4 mol% of APTPOSS)
dIsolated yield
Table 2 Synthesis of
Entry
Aldehyde
R
Product
Time (min)
Yield/a %
m.p °C
3,4,5-substituted furan-2(5H)-
ones using nano-colloidal
silica@APTPOSS (14 mg)
under ultrasonic irradiation
(40 W) in ethanol
1
2
3
4
5
6
7
8
4-Cl-C6H4
C6H5
4-O-Me-C6H4
2-Cl-C6H4
4-Br-C6H4
4-NO2-C6H4
2-NO2-C6H4
3-NO2-C6H4
4-CH(CH3)2-C6H4
4-Cl-C6H4
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
4a
4b
4c
4d
4e
4f
4g
4h
4i
10
10
15
10
10
10
10
10
15
10
10
95
92
86
92
95
96
93
91
88
92
92
148–151 [11]
160–163 [11]
240–243 [11]
274–276 [11]
180–181 [12]
176–179 [10]
200–201 [12]
199–202 [12]
202–204 [12]
181–184 [11]
250–252 [12]
9
10
12
CH3
CH3CH2
CH3CH2
4j
4k
4-NO2-C6H5
aIsolated yield
eight branches of 3-aminopropyltriethoxysilane as catalyst
under ultrasound irradiations. The remarkable advantages
of this methodology are easy workup, short reaction times,
high to excellent product yields, operational simplicity,
little catalyst loading, and use of ultrasonic irradiations as
a valuable and powerful technology.
Conclusion
In conclusion, we demonstrated an efcient method for the
synthesis of 3,4,5-substituted furan-2 (5H)-ones through
a three-component reaction of aniline, dialkyl acetylen-
edicarboxylate, and aromatic aldehydes using nanosil-
ica-tethered polyhedral oligomeric silsesquioxanes with
1 3

Journal of the Iranian Chemical Society
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C
H
Ar1
Ar1
H
H
N
CO2R
O
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+
Ο_
OR
Ar2
H
C
)))))))))))
H
CO2R
CO2R
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I
Ar2
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HN
nano-colloidal silica@APTPOSS
=
RO2C
Ar1
O
O
18. J. Safaei-Ghomi, A. Hatamia, H. Shahbazi-Alavi, A. Ziarati, Sci.
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Scheme 3 Possible mechanism for the synthesis of 3,4,5-substituted
furan-2(5H)-ones in the presence of nano-colloidal silica@APTPOSS
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Acknowledgements The authors are grateful to University of Kashan
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for supporting this work by Grant NO: 159196/XXI.
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1 3