Synthesis and characterization of MgO nanoparticles supported on ionic liquid-based periodic mesoporous organosilica (MgO@PMO-IL) as a highly efficient and reusable nanocatalyst for the synthesis of novel spirooxindole-furan derivatives

Article abstract of DOI:10.1002/aoc.4805

The synthesis and catalytic application of a novel MgO containing periodic mesoporous organosilica with ionic liquid framework (MgO@PMO-IL) is described. The prepared MgO@PMO-IL was characterized by Fourier transform-infrared spectroscopy, N₂ adsorption/desorption, transmission electron microscopy, field emission-scanning electron microscopy, thermogravimetric and inductively coupled plasma analyses. This nanocatalyst was successfully applied as a highly efficient and recoverable catalyst for the synthesis of novel spirooxindole-furan derivatives via the three-component reaction of 1,3-dicarbonyl compounds, N-phenacyl pyridinium salts and isatin derivatives. The products were achieved in high to excellent yields with a simple work-up procedure and short reaction times, and the catalyst could be recovered through a simple filtration process and successfully reused seven times without any significant decrease in its efficiency.

Full text of DOI:10.1002/aoc.4805

Received: 25 September 2018
DOI: 10.1002/aoc.4805
Revised: 30 November 2018
Accepted: 20 December 2018
S P E C I A L I S S U E A R T I C L E
Synthesis and characterization of MgO nanoparticles
supported on ionic liquid‐based periodic mesoporous
organosilica (MgO@PMO‐IL) as a highly efficient and
reusable nanocatalyst for the synthesis of novel
spirooxindole‐furan derivatives
1
2
1
Robabeh Baharfar
| Daryoush Zareyee
| Seyedeh Leila Allahgholipour
1
Department of Organic Chemistry,
Faculty of Chemistry, University of
Mazandaran, 4741695447 Babolsar, Iran
The synthesis and catalytic application of a novel MgO containing periodic
mesoporous organosilica with ionic liquid framework (MgO@PMO‐IL) is
described. The prepared MgO@PMO‐IL was characterized by Fourier
2
Department of Chemistry, Qaemshahr
Branch, Islamic Azad University,
Qaemshar, Iran
transform‐infrared spectroscopy, N adsorption/desorption, transmission elec-
2
tron microscopy, field emission‐scanning electron microscopy, thermogravi-
metric and inductively coupled plasma analyses. This nanocatalyst was
successfully applied as a highly efficient and recoverable catalyst for the syn-
thesis of novel spirooxindole‐furan derivatives via the three‐component reac-
tion of 1,3‐dicarbonyl compounds, N‐phenacyl pyridinium salts and isatin
derivatives. The products were achieved in high to excellent yields with a sim-
ple work‐up procedure and short reaction times, and the catalyst could be
recovered through a simple filtration process and successfully reused seven
times without any significant decrease in its efficiency.
Correspondence
Robabeh Baharfar, Department of Organic
Chemistry, Faculty of Chemistry,
University of Mazandaran, 4741695447,
Babolsar, Iran.
Email: baharfar@umz.ac.ir
KEYWORDS
multi‐component reaction, nanocatalyst, nanoparticles, novel spirooxindole‐furan derivatives,
periodic mesoporous organosilica
1
| INTRODUCTION
Synthesis of spirooxindole‐furan derivatives has been
performed through the interrupted Feist–Benary reac-
[
7]
Spirocyclic compounds with a nitrogen‐containing ring
system fused at central carbon, particularly
spirooxindoles, are important heterocyclic compounds
playing fundamental roles in pharmacological and bio-
logical fields. Spirooxindole derivatives have been used
as antitumor, antimicrobial, antibiotic, anti‐HIV,
tion (IFB)
under homogeneous conditions in the
a
presence of organic and inorganic base catalysts, such
[
8]
as K CO , DBU, DABCO, DIPEA and NEt
3.
However,
2
3
these methods suffer from some disadvantages, includ-
[1]
ing toxicity and expensiveness, difficult work‐up and
[2]
[3]
[4]
[8–14]
catalyst
times,
recovery
processes,
long
reaction
high amounts
and non‐ecofriendly reaction condi-
To overcome these problems, recently
[5]
[8,11–14]
[9,10,12]
antimalarial,
anti‐Alzheimer and anti‐tuberculosis
low reaction yields,
[1]
[9,11–13]
agents. On the other hand, heterocyclic compounds
containing furan rings have effective pharmacological
activities, such as antidepressant, antimicrobial, anti‐
of catalyst,
[
8–14]
tions.
some recoverable heterogeneous catalysts have been
[6]
[15–19]
fungal and anti‐inflammatory properties.
developed.
Appl Organometal Chem. 2019;e4805.
wileyonlinelibrary.com/journal/aoc
© 2019 John Wiley & Sons, Ltd.
1 of 12
https://doi.org/10.1002/aoc.4805

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BAHARFAR ET AL.
In the past few years, periodic mesoporous
yields, low reaction time and simple work‐up in the pres-
ence of a highly efficient and recoverable nanocatalyst.
[8]
organosilica (PMO) hybrid nanomaterials have attracted
much attention because of their uniform pore sizes, large
pore volumes, high surface areas, high loading of organic
functional groups, and good thermal and mechanical
2 | RESULTS AND DISCUSSION
[20,22–31]
stability.
Ionic liquids (ILs) are liquid salts with low‐
temperature melting points (< 100°C), which are used
as media for different applications in various chemical
processes. These materials are good solvents for catalytic
reactions and have many advantages, such as easy separa-
tion, very low vapor pressure, non‐flammability, high
With the purpose of the preparation of a novel
nanocatalyst (MgO@PMO‐IL) with high surface areas,
uniform pore sizes, large pore volumes, high loading of
organic functional groups, and good thermal and
mechanical stability, we designed a method that is shown
in Scheme 2.
[32–36]
thermal stability and low toxicity.
At first, PMO‐IL was prepared by hydrolysis and poly-
merization of tetramethoxysilane and 1,3‐bis(3‐
Ionic liquid‐based PMO (PMO‐IL) is an efficient sup-
port for metal catalysts, and can be recovered and reused
several times without any remarkable decrease in its
[
29]
trimethoxysilylpropyl) imidazolium chloride
using
Pluronic P123 [poly (ethylene glycol)‐poly (propylene gly-
col)‐poly (ethylene glycol)] as a structure‐directing agent.
PMO‐IL was synthesized in a simpler modified procedure
[22–25]
activity and efficiency.
Metal oxide nanoparticles such as magnesium oxide
[
41]
(MgO‐NPs) have been used as heterogeneous catalysts
compared with the last synthesis reports.
We used
in the synthesis of numerous organic compounds because
of their high surface area leading to small particle site
and high concentration of corner/edge. In addition,
MgO nanoparticles have a dual role that contains a num-
sodium imidazolide instead of imidazole and sodium
[
21,30]
hydride
pot process (instead of absence of light condition).
Then, magnesium oxide nanoparticles [MgO‐NPs; 20 nm
and normal reaction conditions in the one‐
[42]
2
−
−
2 −1
ber of (O /O ) as anionic oxidic Lewis basic and OH as a
diameter, specific surface area (SSA): > 60 m g ] were
supported on the pore walls of PMO‐IL in dimethyl sulf-
oxide to produce MgO@PMO‐IL nanocatalyst. The pre-
pared nanocatalyst was characterized by various selected
2+
hydroxylic Brønsted basic site along with Mg as a Lewis
[37]
acid site.
For these reasons, we immobilized MgO
nanoparticles on PMO‐IL for the first time for the synthe-
sis of a novel nanocatalyst as MgO@PMO‐IL.
techniques, including N adsorption/desorption, Fourier
2
Due to expanding the scope of the IFB reaction, and
in continuation of our previous works for the synthesis
of novel heterocyclic compounds using heterogeneous
transform‐infrared (FT‐IR), thermogravimetric analysis
(TGA), transmission electron microscopy (TEM) and field
emission‐scanning electron microscopy (FE‐SEM).
FT‐IR of PMO‐IL (Figure 1) showed a broad peak at
[37–40]
catalysts,
we have developed a strategy for the prep-
−
1
aration of a novel MgO containing PMO‐IL (MgO@PMO‐
IL) and examined its application in the Feist–Benary
reaction for the synthesis of novel spirooxindole‐furan
derivatives via three‐component reaction of isatin deriva-
tives with 1,3‐dicarbonyl compounds and N‐phenacyl
pyridinium salts (Scheme 1). The products were synthe-
sized under green reaction conditions with excellent
3448 cm for the O‐H stretching vibration, and a peak
−
1
at 2924 cm for saturated C‐H stretching. In addition,
−
1
other absorption bands were observed at 1634 cm for
C=N stretching of the imidazolium ring, at 1090 and
−
1
964 cm for asymmetric and symmetric stretching vibra-
−
1
tions of Si‐O‐Si, at 799 cm for C‐Si stretching, and at
−
1
465 cm for Si‐O‐Si bending vibration.
SCHEME 1 Preparation of 6‐benzoyl‐1,3‐dimethyl‐1H‐spiro [furo [2,3‐d]pyrimidine‐5,3′‐indoline]‐ 2,2′,4(3H,6H)‐trione (4c) in the
presence of MgO@PMO‐IL

BAHARFAR ET AL.
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SCHEME 2 Preparation of the
MgO@PMO‐IL nanocatalyst
FIGURE 1 Fourier transform‐infrared
spectroscopy (FT‐IR) of ionic liquid‐based
periodic mesoporous organosilica
(
PMO‐IL)
Thermogravimetric analysis of PMO‐IL (Figure 2)
Moreover, the PMO‐IL displayed a high Brunauer–
2
−1
showed a weight loss of about 5% below 100°C related
to elimination of water. Also, 2% mass loss occurring
from 100 to 232°C and the main weight loss of 17% from
32 to 800°C can be attributed to the pyrolysis of P123
and IL functional groups. The results of TGA clearly dem-
onstrate the high thermal stability of the catalyst.
Emmett–Teller surface area of 623 m g with a total
3
−1
pore volume of 1.89 cm g , and the Barrett–Joyner–
Halenda calculations illustrated highly uniform pore
diameter distribution of 5.3 nm for PMO‐IL. Further-
more, decreasing SSA and pore volume of MgO@PMO‐
2
2
−1
3 −1
IL to 523 m g and 0.80 cm g clearly showed that
MgO has been successfully immobilized inside the pores
of the PMO‐IL (see Supporting Information).
As can be seen in Figure 3, N adsorption–desorption
2
analysis of PMO‐IL showed a type IV isotherm with an
H1 hysteresis loop, which is characteristic of mesoporous
materials with a uniform pore size distribution.
Scanning
emission
microscopy
analysis
of
[
23,43]
MgO@PMO‐IL was also performed to study the

4
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BAHARFAR ET AL.
FIGURE 2 Thermogravimetric analysis
(
TGA) of the ionic liquid‐based periodic
mesoporous organosilica (PMO‐IL)
morphology of the material (Figure 4a and b). These
images illustrate a uniform structure. The TEM image of
MgO@PMO‐IL (Figure 4c) clearly showed a two‐
dimensional hexagonal mesostructure with a well‐
ordered and regular mesoporous. These SEM and TEM
images were in good agreement with the data obtained
from nitrogen sorption.
Finally, the MgO content in MgO@PMO‐IL was
−
1
determined to be 0.6 mmol g using the induced coupled
plasma (ICP) technique.
To investigate the catalytic performance of the syn-
thesized MgO@PMO‐IL, we chose the three‐component
reaction of 1,3‐dimethyl barbituric, N‐phenacyl
pyridinium bromide and isatin as model reaction
(
(
Scheme 1), and studied different reaction parameters
Table 1). First, the model reaction in the presence of
MgO@PMO‐IL nanocatalyst was examined in various
solvents, including tetrahydrofuran, dichloromethane,
water, combination of water and ethanol (1:1), and
solvent‐free conditions at 50°C (Table 1, entries 1–6). It
was found that ethanol gave the best result with 95%
yield in 40 min. The reaction time and the product yield
in the presence of MgO@PMO‐IL in ethanol did not
change with increasing the temperature to 78°C
(
Table 1, entries 6–8). The effect of catalyst amount on
the reaction conditions was also explored, and it was
observed that the use of 1 mol% MgO@PMO‐IL is suffi-
cient to conduct the model reaction with excellent yield
in short reaction time (Table 1, entries 6, 9 and 10).
FIGURE 3 (a) N
distributions isotherms of ionic liquid‐based periodic mesoporous
organosilica (PMO‐IL) and MgO@PMO‐IL
2
adsorption–desorption; and (b) pore size
[
37]
Performing the model reaction with MgO
and PMO‐
IL significantly decreased the product yield and the

BAHARFAR ET AL.
5 of 12
FIGURE 4 Scanning electron microscopy (SEM) images (a and b) and transmission electron microscopy (TEM) image (c) of MgO@PMO‐
IL catalyst
reaction rate in comparison with MgO@PMO‐IL
molecular ion peak at m/z: 437, which is consistent with
the molecular weight of this product. The IR spectrum of
(Table 1, entries 11 and 12).
−
1
The efficiency of MgO@PMO‐IL nanocatalyst was
compared with different homogeneous catalysts, includ-
4d showed a broad peak at 3452 cm corresponding to
the vibration of the N‐H group, and a sharp peak at
−
1
ing K CO , DBU, DABCO and NEt in ethanol at 50°C
2955 cm that is related to saturated C‐H stretching.
2
3
3
−
1
(Table 1, entries 13–16). As shown, MgO@PMO‐IL gave
Moreover, the peaks in the region 1742–1643 cm are
1
more yield and shorter reaction time than homogenous
catalysts in ethanol at 50°C (Table 1, entry 6). In addition,
the reaction did not proceed in the absence of any catalyst
related to the C=O stretching. The H‐NMR spectrum of
4d in CDCl showed two singlets at 3.23 and 3.57 ppm
3
related to the two methyl groups of barbiturate acid,
3
(Table 1, entry 17). Thus, MgO@PMO‐IL was selected
one doublet at 6.28 ppm ( J = 9.2 Hz) for the CH group
HH
as an optimum catalyst for the model reaction in ethanol
at 50°C.
of oxindole, and one singlet at 6.57 ppm associated to the
CH group of the furan ring. The aromatic protons
appeared as three multiplets at about 6.90–6.93,
7.26–7.30 and 7.44–7.47 ppm. The NH proton of oxindole
appeared as one broad singlet at 8.95 ppm. The proton‐
decoupled C‐NMR spectrum of 4d showed 22 distinct
resonances in agreement with the proposed structure,
including two signals at 27.9 and 30.1 ppm for N‐CH3,
and two signals at 58.8 and 91.1 ppm for the spiro carbon
atom and the furan carbon atom, respectively.
In order to expand the scope of the reaction, we
used MgO@PMO‐IL for the synthesis of novel
spirooxindole‐furan derivatives through the three‐
component reaction of 1,3‐dicarbonyl compounds with
N‐phenacyl pyridinium salts and isatin derivatives
13
(Table 2) under the optimized reaction conditions, and
the products were obtained in high yields at short reac-
tion times.
The structures of novel spirooxindole‐furan deriva-
A plausible mechanism is illustrated in Scheme 3,
which is supported by the previous literature.
To evaluate the recoverability and reusability
of MgO@PMO‐IL, we used this catalyst in the three‐
1
13
[8,40]
tives were confirmed by FT‐IR, H‐NMR, C‐NMR and
mass spectroscopy (see Supporting Information). For
instance, the mass spectrum of 4d exhibited the

6
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BAHARFAR ET AL.
a
TABLE 1 Optimization for the three‐component reaction of 1,3‐dimethyl barbituric, N‐phenacyl pyridinium bromide and isatin
Entry
Catalyst (mol%)
Solvent
Temp. (°C)
Time
Yield (%)
1
2
3
4
5
6
7
8
9
MgO@PMO‐IL (1)
MgO@PMO‐IL (1)
MgO@PMO‐IL (1)
MgO@PMO‐IL (1)
MgO@PMO‐IL (1)
MgO@PMO‐IL (1)
MgO@PMO‐IL (1)
MgO@PMO‐IL (1)
MgO@PMO‐IL (0.7)
MgO@PMO‐IL (1.5)
PMO‐IL (1)
DCM
50
50
50
50
50
50
25
78
50
50
50
50
50
50
50
50
50
8 hr
65
65
70
50
60
95
70
96
70
96
25
80
45
60
65
85
–
H
H
2
2
O
6 hr
O‐Ethanol (1:1)
5 hr
THF
8 hr
–
10 hr
40 min
8 hr
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
40 min
40 min
40 min
6 hr
10
11
12
13
14
15
16
17
MgO (1)
2 hr
K
2
CO
3
(1)
15 hr
15 hr
18 hr
10 hr
24 hr
DBU (1)
DABCO (1)
3
NEt (1)
–
a
Reaction conditions: 1,3‐dimethyl barbituric acid (1 mmol), N‐phenacyl pyridinium bromide (1 mmol) and isatin (1 mmol).
component reaction of 1,3‐dimethyl barbituric, N‐
phenacyl pyridinium bromide and isatin under the opti-
mized conditions. The catalyst was recovered through a
simple filtration process and reused for at least seven
times without a significant decrease in its catalytic activ-
ity (Figure 5).
products were prepared under mild reaction conditions
with good yields, short reaction times and a simple
work‐up procedure. In addition, the catalyst was recov-
ered and reused for at least seven times without a signif-
icant decrease in its catalytic activity.
The FT‐IR analysis of the recovered catalyst (Figure 6)
showed that the stability of IL units during reaction con-
ditions was in good agreement with the data achieved
from the recoverability of the nanocatalyst.
4
| EXPERIMENTAL
All of the chemicals and solvents were purchased from
Merck and Aldrich without need for further purification.
The progress of the reactions was monitored by thin‐layer
chromatography (TLC) using silica gel SIL G/UV 254
plates. Melting points were measured on an Electrother-
mal 9100 apparatus and are uncorrected. IR spectra
(KBr) were recorded on a FT‐IR BRUKER VECTOR 22
spectrometer. H‐ and C‐NMR spectra were measured
with Bruker DRX‐400 Avance instrument (400.13 and
100.61 MHz, respectively), and Bruker Avance 300 NMR
3
| CONCLUSION
In conclusion, with the aim of preparing a novel
nanocatalyst, the supported nano‐MgO on PMO‐IL
1
13
(MgO@PMO‐IL) with uniform pore size, large pore vol-
umes, high surface areas, high loading of organic func-
tional groups and good thermal stability was
synthesized
and
then
characterized
by
N2
(300.13 and 75.46 MHz, respectively) in CDCl and (D6)
3
adsorption/desorption, FT‐IR, TEM, FE‐SEM, TGA and
ICP analyses. The catalytic performance of MgO@PMO‐
IL was investigated in the synthesis of novel
spirooxindole‐furan derivatives through the three‐
component reaction of 1,3‐dicarbonyl compounds, N‐
phenacyl pyridinium salts and isatin derivatives. These
DMSO. Mass spectra were recorded on a Finnigan‐Matt
8430 mass spectrometer operating at an ionization poten-
tial of 70 eV. The TGA was measured by BAHR‐
Thermoanalyse (GmbH STA 503) from room temperature
to 800°C. The size and structure of the materials were
shown using TEM (Zeiss‐EM10C‐100 kV), FE‐SEM

BAHARFAR ET AL.
7 of 12
a
TABLE 2 Synthesis of novel spirooxindole‐furan derivatives in the presence of MgO@PMO‐Il
1
2
3
Entry
R
R
R
1‐3‐Dicarbonyl compound
Product
4a
Time (min)
m.p. (°C)
Yield (%)
b
b
1
H
H
H
H
H
40
275–276 (275–277)
90
2
Cl
4b
40
261–263 (260–263)
95
b
3
4
H
H
H
H
H
4c
4d
40
30
244–248 (245–247)
297–300
95
97
Cl
5
6
H
CH
CH
3
2
H
H
4e
4f
50
30
216–218
213–215
90
95
Cl
CO
2
Et
7
8
H
H
PhCH
2
H
H
4 g
4 h
30
30
261–263
225–227
97
97
CH
2
2
CO
2
CH
3
9
H
H
Cl
CH
H
C ≡ CH
H
F
4i
30
30
30
261–263
229–231
322–324
97
95
95
1
1
0
1
4j
H
F
4 k
a
Reaction conditions: 1,3‐dicarbonyl compound (1 mmol), N‐phenacyl pyridinium salt (1 mmol) and isatin derivatives (1 mmol), MgO@PMO‐IL (1 mol%),
EtOH (5 mL), 50°C, stirring.
b
Reported m.p.
(
MIRA3 XMU), and were verified further by N2
xysilane (1.35 mL) were added to a well‐dried two‐
necked flask containing dry THF (20 mL). The mixture
was stirred under reflux conditions for 24 hr under argon
atmosphere. Then it was cooled to room temperature
and the solvent was removed under reduced pressure.
Thereafter, 3‐chloropropyltrimethoxysilane (1.35 mL)
and dry toluene (20 mL) were added, and the mixture
was heated at 80°C for 48 hr. The toluene phase was
adsorption/desorption analysis [BELsorp‐max (Japan)].
The ICP technique was determined by VARIAN VISTA‐
PRO instrument.
4
.1 | Synthesis of imidazolium ionic liquid
The IL was prepared according to the previously reported
removed, and then dry CH
NaCl. The CH Cl phase was transferred to another
flask, and CH Cl was removed under reduced pressure.
2 2
Cl was added to precipitate
[30,35,42]
procedures with a few modifications.
Typically,
2
2
sodium imidazolide (0.5 g) and 3‐chloropropyltrimetho
2
2

8
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BAHARFAR ET AL.
SCHEME 3 Proposed mechanism for the preparation of spirooxindole‐furan derivatives using MgO@PMO‐IL as heterogenous
nanocatalyst
Finally, the obtained viscous yellow product was washed
with dry toluene several times.
4.2 | Synthesis of PMO‐IL
The PMO‐IL was synthesized according to the last
[
30,35,42]
reported literature.
P123 (1.67 g), KCl (8.8 g),
HCl (2 M, 46.14 g) and distilled H O (10.5 g) were mixed
2
and stirred at 40°C until a homogenous solution was
obtained. Then IL (0.86 g) and
a
solution of
tetramethoxysilane (2.74 g) in dry methanol were added
to the mixture and stirred at 40°C for 24 hr, then it was
aged at 100°C for 48 hr. Thereafter, the mixture was
cooled to room temperature and washed with deionized
water. The surfactant was extracted by a Soxhlet extractor
FIGURE 5 Recyclability test of MgO@PMO‐IL during the three‐
component reaction of 1,3‐ dimethyl barbituric acid with N‐
phenacyl pyridinium bromide and isatin in the presence of
MgO@PMO‐IL in ethanol at 50°C

BAHARFAR ET AL.
9 of 12
FIGURE 6 Fourier transform‐infrared
(
FT‐IR) analysis of the recovered
MgO@PMO‐IL
1
using ethanol (100 mL) and HCl (3 mL) for each 1 g of
PMO‐IL for six times over 12 hr. Finally, PMO‐IL was
dried at 50°C in vacuum.
(C=O), 1476 (C=C), 1257 (Csp2 ‐O), 1065 (Csp3‐O); H‐
NMR (400 MHz, CDCl ), δ (ppm): 1.15 and 1.22 (2 s,
6H, 2CH ), 2.13 and 2.31 (2d, 2H, J = 16.4 Hz, AB‐
system, CH ), 2.64 and 2.70 (2d, 2H, JHH = 18.0 Hz,
AB‐system, CH ), 6.46 (d, 1H, J = 7.6 Hz, CHOxindole),
3
H
2
3
HH
2
2
3
2
HH
4.3 | Synthesis of MgO@PMO‐IL
6
.47 (s, 1H, CHfuran), 6.87–6.88 (m, 2H, 2CH ), 6.97–7.01
Ar
(
3
m, 1H, CH ), 7.23–7.28 (m, 2H, 2CH ), 7.40–7.45 (m,
Ar
Ar
First, PMO‐IL (0.2 g) was dispersed in DMSO (1 mL).
Then, nano‐MgO (0.1 mmol) was added and the mixture
was stirred at 50°C for 6 hr, and then at 100°C for 2 hr.
Subsequently, the mixture was cooled to room tempera-
ture and washed with ethanol several times and dried at
13
H, 3CH ), 7.79 (br s, 1H, NH); C‐NMR (100 MHz,
Ar
CDCl ), δ (ppm): 27.7 and 29.4 (2CH ), 34.5 (CMe ),
3
(
1
1
1
3
C
3
2
7.7 and 50.8 (2CH ), 58.9 (Cspiro), 91.4 (CHfuran), 109.6
2
CH ), 114.5 (Cq), 122.9 and 124.8 (2CH ), 126.5 (Cq),
Ar Ar
27.5 and 128.5 (4CH ), 129.1 and 133.7 (2CH ),
Ar Ar
6
0°C for 12 hr.
34.6, 139.6 and 177.3 (3Cq), 178.1 (COamide), 192.2 and
+
●
92.3 (2COketone); MS, m/z: 387 (M ).
4.4 | General procedure for the synthesis
of compounds 4a–k
4
6
.5.2 | 2‐Benzoyl‐5′‐chloro‐6,6‐dimethyl‐
,7‐dihydro‐2H‐spiro [benzofuran‐3,3′‐
A mixture of 1,3‐dicarbonyl compounds (1 mmol), isatin
indoline]‐2′,4(5H)‐dione (4b)
(1 mmol) and N‐phenacyl pyridinium bromide (1 mmol)
in ethanol (5 mL) in the presence of MgO@PMO‐IL (1
mol%) as catalyst was stirred at 50°C for the specified time
period. The reaction was monitored by TLC (EtOAc/n‐
hexane, 1:1). After completion of the reaction, the solvent
was evaporated under reduced pressure and the product
was obtained by recrystallization from methanol.
White powder, m.p.: 261–263°C; yield (0.40 g, 95%); IR
−
1
(
KBr) (vmax, cm ): 3291 (NH), 2958 (C ‐H), 1727–1644
sp3
1
(
C=O), 1223 (Csp2 = O), 1065 (Csp3 = O); H‐NMR (400
MHz, CDCl ), δ (ppm): 1.20 and 1.30 (2 s, 6H, 2CH ),
3
H
3
2
2
2
6
.17 and 2.30 (2d, 2H, J = 16.4 Hz, AB‐system, CH2),
.64 and 2.71 (2d, 2H, J = 18.0 Hz, AB‐system, CH2),
.40 (d, 1H, JHH = 8.4 Hz, CHOxindole), 6.46 (s, 1H,
CHfuran), 6.85 (d, 1H, JHH = 2.4 Hz, CHAr), 6.97 (dd, 1H,
HH
2
HH
3
4
4.5 | Physical and spectral data for
3
4
compounds 4a–k
J
HH = 8.4 Hz, JHH = 2.0 Hz, CHAr), 7.27–7.31 (m, 2H,
2
CH ), 7.44–7.48 (m, 3H, 3CH ), 7.77 (br s, 1H, NH);
Ar
Ar
13
4.5.1 | 2‐Benzoyl‐6,6‐dimethyl‐6,7‐dihydro‐
2H‐spiro [benzofuran‐3,3′‐indoline]‐
2′,4(5H)‐dione (4a)
C‐NMR (100 MHz, CDCl
3
), δ
C
(ppm): 28.0 and 29.2
), 58.9 (Cspiro),
91.2 (CHfuran), 110.6 (CHAr), 114.3 (Cq), 125.1 and 127.6
4CH ), 128.2 and 128.3 (2Cq), 128.7, 129.1 and 133.9
(2CH ), 34.5 (CMe ), 37.7 and 50.8 (2CH
3 2 2
(
Ar
White powder, m.p.: 275–276°C; yield (0.34 g, 90%); IR
(3CH ), 134.5, 138.3 and 176.9 (3Cq), 178.6 (CO
191.9 and 192.3 (2COketone); MS, m/z: 423 and 421 (M ).
),
amide
Ar
−
1
+●
(KBr) (vmax, cm ): 3430 (NH), 2939 (Csp3‐H), 1725–1645

10 of 12
BAHARFAR ET AL.
4
[
2
.5.3 | 6‐Benzoyl‐1,3‐dimethyl‐1H‐spiro
furo [2,3‐d]pyrimidine‐5,3′‐indoline]‐
,2′,4(3H,6H)‐trione (4c)
108.1, 123.2 and 124.8 (3CHAr), 125.2 (Cq), 127.4 and
128.4 (4CHAr), 129.7 and 133.8 (2CHAr), 134.2, 142.5
and 151.3 (3Cq), 158.0, 163.1 and 175.3 (3COamide),
+
●
190.7 (COketone); MS, m/z: 417 (M ).
White powder, m.p.: 244–248°C; yield (0.38 g, 95%); IR
−
1
(
(
KBr) (vmax, cm ): 3430 (NH), 2925 (C ‐H), 1709–1646
sp3
1
C=O), 1190 (Csp2‐O), 1111 (Csp3‐O); H‐NMR (400
MHz, CDCl ), δ (ppm): 3.23 and 3.58 (2 s, 6H, 2 N‐
4.5.6 | Ethyl 2‐(6‐benzoyl‐5′‐chloro‐1,3‐
dimethyl‐2,2′,4‐trioxo‐2,3,4,6‐tetrahydro‐1H‐
spiro [furo[2,3‐d]pyrimidine‐5,3′‐indolin]‐
1′‐yl) acetate (4f)
3
H
3
CH ), 6.48 (d, 1H, JHH = 7.6 Hz, CH
), 6.60 (s,
3
Oxindole
4
3
1
H, CHfuran), 6.90 (td, 1H, J = 7.6 Hz, J = 0.8 Hz,
HH HH
3
4
CH ), 6.94 (td, 1H, J = 8.0 Hz, J = 0.8 Hz, CHAr),
Ar
HH
HH
3
4
7
.01 (td, 1H, J = 7.6 Hz, J = 1.6 Hz, CH ), 7.25–
HH
HH
Ar
7
.29 (m, 2H, 2CH ),7.42–7.47 (m, 3H, 3CH ), 7.97 (br
White powder, m.p.: 216–218°C; yield (0.50 g, 95%); IR
Ar
Ar
13
−1
s, 1H, NH); C‐NMR (100 MHz, CDCl ), δ (ppm): 27.9
and 30.1 (2CH ), 58.8 (Cspiro), 91.1 (CHfuran), 109.9 and
1
(KBr) (vmax, cm ): 3434 (NH), 2924 (C ‐H), 1746–1613
3
C
sp3
1
(C=O), 1216 (Csp2‐O), 1175 (Csp3‐O); H‐NMR (400
3
3
23.2 (2CH ), 125.4 and 125.6 (2Cq), 127.5 and 128.7
MHz, CDCl ), δ (ppm): 1.33 (t, 3H, JHH = 7.2 Hz,
Ar
3
H
(
(
(
4CH ), 129.6 and 134.1 (2CH ), 139.7 (Cq), 148.0
CH ), 3.21 and 3.57 (2 s, 6H, 2 N‐CH ), 4.27 (m, 2H,
Ar
Ar
3
3
2
CH ), 151.4 and 158.1 (2Cq), 163.2, 176.9 and 179.8
OCH ), 4.28 and 4.63 (2d, 2H, J = 17.6 Hz, AB‐system,
Ar
2
HH
+
●
3
3COamide), 190.6 (COketone); MS, m/z: 403 (M ).
N‐CH ), 6.43 (d, 1H, J = 8.4 Hz, CHOxindole), 6.57 (s,
2
HH
4
furan HH Ar
1
(
2
2
H, CH
), 6.94 (d, 1H, J = 2.0 Hz, CH ), 7.037
3
4
dd, 1H, JHH = 8.4 Hz, JHH = 2.0 Hz, CH ), 7.35 (t,
Ar
4
.5.4 | 6‐Benzoyl‐5′‐chloro‐1,3‐dimethyl‐
H‐spiro [furo [2,3‐d]pyrimidine‐5,3′‐
3
3
H, J = 7.6 Hz, 2CH ), 7.48 (t, 1H, J = 7.6 Hz,
HH Ar HH
1
3
13
CH ), 7.56 (d, 2H, J = 8.8 Hz, 2CHAr); C‐NMR
Ar
HH
indoline]‐2,2′,4(3H,6H)‐trione (4d)
(
100 MHz, CDCl ), δ (ppm): 14.2, 27.9 and 30.1 (3CH ),
3
C
3
4
2.0 (N‐CH ), 58.1 (C
), 62.0 (CH ), 88.7 (Cq), 89.9
2
spiro
2
White powder, m.p.: 297–300°C; yield (0.42 g, 97%); IR
(
(
(
CHfuran), 109.3 and 125.8 (2CH ), 126.4 (Cq), 127.9
2CH ), 129.0 (Cq), 129.1 (2CH ), 129.6 (CH ), 133.7
Cq), 134.3 (CH ), 140.4 and 151.2 (2Cq), 157.9 (COester),
−
1
Ar
(
KBr) (vmax, cm ): 3452 (NH), 2955 (C ‐H), 1742–1643
sp3
1
Ar
Ar
Ar
(C=O), 1255 (Csp2‐O), 1182 (Csp3‐O); H‐NMR (400
Ar
MHz, CDCl ), δ (ppm): 3.24 and 3.58 (2 s, 6H, 2 N‐
3
H
163.5, 166.7 and 175.4 (3COamide), 190.0 (COketone); MS,
3
CH ), 6.28 (d, 1H, JHH = 9.2 Hz, CHOxindole), 6.57 (s,
3
+●
m/z: 523 (M ).
1
2
H, CHfuran), 6.90–6.93 (m, 2H, 2CH ), 7.26–7.30 (m,
Ar
H, 2CH ), 7.44–7.47 (m, 3H, 3CH ), 8.95 (br s, 1H,
Ar
Ar
13
NH); C‐NMR (100 MHz, CDCl ), δ (ppm): 28.0 and
3
C
3
1
1
1
1
0.2 (2CH ), 58.5 (Cspiro), 89.0 (Cq), 91.1 (CHfuran),
3
4
.5.7 | 6‐Benzoyl‐1′‐benzyl‐1,3‐dimethyl‐
H‐spiro [furo[2,3‐d]pyrimidine‐5,3′‐
11.2. and 125.4 (2CH ), 127.2 (Cq), 127.6 (2CH ),
Ar
Ar
1
28.3 (Cq), 128.8 (2CH ), 129.6 (CH ), 133.9 (Cq),
Ar
Ar
indoline]‐2,2′,4(3H,6H)‐trione (4g)
34.2 (CH ), 138.9 and 151.0 (2Cq), 158.5, 163.5 and
Ar
+
●
76.4 (3COamide), 190.2 (COketone); MS, m/z: 437 (M ).
White powder, m.p.: 213–215°C; yield (0.48 g, 97%); IR
−
1
(
KBr) (vmax, cm ): 3434 (NH), 2926 (C ‐H), 1722–1665
sp3
1
4
.5.5 | 6‐Benzoyl‐1,1′,3‐trimethyl‐1H‐spiro
furo [2,3‐d]pyrimidine‐5,3′‐indoline]‐
,2′,4(3H,6H)‐trione (4e)
(2C=O), 1216 (Csp2‐O), 1175 (Csp3‐O); H‐NMR (400
MHz, CDCl ), δ (ppm): 3.24 and 3.59 (2 s, 6H, 2 N‐
CH ), 4.55 and 5.11(2d, 2H, JHH = 16 Hz, AB‐system,
N‐CH ), 6.31 (d, 1H, J = 7.6 Hz, CHOxindole), 6.64 (s,
[
2
3
H
2
3
3
2
HH
White powder, m.p.: 233–237°C; yield (0.40 g, 97%); IR
1H, CHfuran), 6.87–6.91 (m, 1H, CH ), 6.94–6.99 (m,
Ar
−
1
(
KBr) (vmax, cm ): 3520 (NH), 2937 (C ‐H), 1722–1612
2H, 2CH ), 7.13–7.17 (m, 2H, 2CH ), 7.27–7.36 (m,
sp3
1
Ar
Ar
13
(C=O), 1261 (Csp2‐O), 1194 (Csp3‐O); H‐NMR (400
7H, 2CH ), 7.41–7.46 (m, 1H, CH ); C‐NMR (100
Ar
Ar
MHz, CDCl ), δ (ppm): 3.10, 3.20 and 3.58 (3 s, 9H,
MHz, CDCl ), δ (ppm): 28.0 and 30.1 (2 N‐CH ), 44.6
3
H
3
C
3
3
3
N‐CH ), 6.42 (d, 1H, J = 8.0 Hz, CHOxindole), 6.58
(N‐CH ), 58.3 (Cspiro), 89.4 (Cq), 91.1 (CHfuran), 109.3
3
HH
2
(
s, 1H, CHfuran), 6.92–6.98 (m, 2H, 2CH ), 7.08 (td, 1H,
and 123.3 (2CH ), 125.1 and 125.2 (2Cq), 127.1 and
Ar
Ar
3
4
JHH = 6.4 Hz, JHH = 2 Hz, CH ), 7.22–7.25 (m, 2H,
127.5 (4CH ), 127.6 (Cq), 128.6 and 128.9 (4CH ),
Ar
Ar
Ar
2
CH ), 7.28–7.31 (m, 2H, 2CH ), 7.49 (m, 1H, CH );
129.5 and 133.9 (2CH ), 134.2 and 134.7 (2Cq), 141.9
Ar
Ar
Ar
Ar
1
3
C‐NMR (100 MHz, CDCl ), δ (ppm): 26.8 and 27.9,
and 151.3 (2Cq), 157.9, 163.0 and 175.6 (3COamide),
3
C
+
●
3
0.1 (3CH ), 58.3 (Cspiro), 89.0 (Cq), 91.7 (CHfuran),
190.7 (COketone); MS, m/z: 493 (M ).
3

BAHARFAR ET AL.
11 of 12
1
4
.5.8 | Methyl 2‐(6‐benzoyl‐1,3‐dimethyl‐
,2′,4‐trioxo‐2,3,4,6‐tetrahydro‐1H‐spiro
(C=O), 1259 (Csp2‐O), 1230 (Csp3‐O); H‐NMR (400
MHz, CDCl ), δ (ppm): 3.23 and 3.56 (2 s, 6H, 2 N‐
CH ), 6.47 (d, 1H, JHH = 7.7 Hz, CHOxindole), 6.53 (s,
1H, CHfuran), 6.86–7.03 (m, 5H, CHAr), 7.56 (dd, 2H, JHH
2
3
H
3
[
furo[2,3‐d]pyrimidine‐5,3′‐indolin]‐1′‐yl)
3
3
acetate (4h)
4
13
=
9.0 Hz, J = 6 Hz, CH ), 8.50 (br s, 1H, NH); C‐
HH
Ar
White powder, m.p.: 225–227°C; yield (0.46 g, 97%); IR
NMR (100 MHz, CDCl ), δ (ppm): 28.0 and 30.1
3 C
−
1
(
KBr) (vmax, cm ): 3442 (NH, OH), 2924 (C ‐H),
(2CH ), 58.6 (Cspiro), 89.3 (Cq), 90.1 (CHfuran), 110.3,
sp3
3
1
1
755–1662 (C=O), 1262 (Csp2‐O), 11 203 (Csp3‐O); H‐
123.1 and 125.2 (5CH ), 125.4 (Cq), 129.7 (CH ), 130.2
Ar
Ar
NMR (400 MHz, CDCl ), δH (ppm): 3.21 and 3.58 (2 s,
and 130.3 (2CH ), 130.5 (Cq), 140.0 (CH ), 151.1 (Cq),
3
Ar
Ar
6
H, 2 N‐CH ), 3.83 (s, 3H, OCH ), 4.35–4.65 (2d, 2H,
158.3, 163.2 and 176.9 (3COamide), 189.0 (COketone); MS,
m/z: 421 (M ).
3
3
2
3
+●
JHH = 17.6 Hz, AB‐system, N‐CH ), 6.50 (d, 1H, J
=
2
HH
7
.6 Hz, CH
), 6.58 (s, 1H, CHfuran), 6.89 (td, 1H,
Oxindole
4
3
3
JHH = 7.6 Hz, J = 0.8 Hz, CH ), 6.97 (dd, 1H, J
=
Hz, JHH = 1.2 Hz, CH ), 7.33–7.34 (m, 2H, 2CH ),
7
HH
Ar
HH
4
.5.11 | 5′‐Chloro‐6‐(4‐fluorobenzoyl)‐1,3‐
dimethyl‐1H‐spiro [furo[2,3‐d]pyrimidine‐
,3′‐indoline]‐2,2′,4(3H,6H)‐trione (4k)
4
3
7.6 Hz, J = 0.8 Hz, CH ), 7.07 (td, 1H, J = 7.6
HH Ar HH
4
Ar
Ar
5
13
.46 (m, 1H, CH ), 7.52–7.54 (m, 2H, 2CH ); C‐NMR
Ar
Ar
(
(
(
(
(
100 MHz, CDCl ), δ (ppm): 27.9 and 30.1 (2CH ), 41.8
3 C 3
White powder, m.p.: 322–324°C; yield (0.43 g, 95%); IR
N‐CH ), 52.8 (OCH ), 57.1 (Cspiro), 83.7 (Cq), 90.2
−1
2
2
(
KBr) (vmax, cm ): 3447 (NH), 2922 (C ‐H), 1741–1598
sp3
1
CHfuran), 108.3 and 123.6 (2CH ), 124.7 (Cq), 125.4
Ar
(
C=O), 1233 (Csp2‐O), 1202 (Csp3‐O); H‐NMR (400
CH ), 127.8 and 128.9 (4CH ), 129.7 (CH ), 133.7
Ar
Ar
Ar
MHz, CDCl ), δ (ppm): 3.24 and 3.57 (2 s, 6H, 2 N‐
3
H
Cq), 134.1 (CH ), 141.8 and 151.6 (2Cq), 154.8 (COacid),
3
Ar
CH ), 6.38 (d, 1H, J = 8.3 Hz, CHOxindole), 6.52 (s,
3
HH
1
57.9, 167.5 and 176.2 (3COamide), 190.4 (COketone); MS,
3
1
H, CHfuran), 6.92–6.92 (d, 1H, JHH = 3 Hz, CH ),
.97–7.00 (m, 3H, 3CH ), 7.50 (dd, 2H, J = 9.0 Hz,
JHH = 6 Hz, CH ), 8.54 (br s, 1H, NH); C‐NMR (100
Ar
+
●
m/z: 475 (M ).
3
6
Ar
HH
4
13
Ar
MHz, DMSO and CDCl ), δ (ppm): 27.1 and 29.4
4
.5.9 | 6‐Benzoyl‐1,3‐dimethyl‐1′‐(prop‐2‐
yn‐1‐yl)‐1H‐spiro [furo[2,3‐d]pyrimidine‐
,3′‐indoline]‐2,2′,4(3H,6H)‐trione (4i)
3
C
(
2CH ), 58.0 (Cspiro), 88.1 (Cq), 90.3 (CHfuran), 110.5,
3
1
24.7 and 126.6 (5CH ), 127.2 (Cq), 128.7 and 129.8
5
Ar
(
2CH ), 129.9, 130.1 and 130.2 (3Cq), 139.6 (CH ),
Ar Ar
White powder, m.p.: 261–263°C; yield (0.43 g, 97%); IR
150.5 (Cq), 157.1, 162.6 and 176.0 (3COamide), 188.7
(COketone); MS, m/z: 455 (M ).
−
1
+●
(
KBr) (vmax, cm ): 3443 (NH), 2924 (C ‐H), 1710–1613
sp3
1
(C=O), 1262 (Csp2‐O), 1186 (Csp3‐O); H‐NMR (400
4
MHz, CDCl ), δ (ppm): 2.23 (t, 1H, JHH = 2.4 Hz,
3
H
ACKNOWLEDGEMENT
CHalkin), 3.20 and 3.57 (2 s, 6H, 2 N‐CH ), 4.31 and 4.70
3
3
4
(
2
2d, 2H, JHH = 7.6 Hz, JHH = 2.4 Hz, AB‐system,
CHOxindole), 6.60 (s, 1H, CHfuran), 6.74 (d, 1H, J = 8
Hz, CH ), 6.92–6.99 (m, 2H, CH ), 7.19 (td, 1H, J
7.6 Hz, JHH = 1.6 Hz, CH ), 7.24–7.26 (m, 2H,
The authors would like to thank the Research Council of
Mazandaran University for financial support.
2
HH
3
Ar
Ar
HH
4
=
Ar
CONFLICT OF INTEREST
2
CH ), 7.36–7.38 (m, 2H, 2CH ), 7.40–7.44 (m, 1H,
Ar
Ar
13
CH ); C‐NMR (100 MHz, CDCl ), δ (ppm): 27.9 and
There are no conflicts to declare.
Ar
3
C
3
0.1 (2CH ), 30.1 (CH), 58.2 (Cspiro), 72.8 (Calkin), 76.0
3
(
1
Cq), 89.1 (Cq), 90.9 (CHfuran), 109.2 and 123.6 (2CHAr),
ORCID
25.0 and 125.1 (2Cq), 127.3 and 128.8 (4CH ), 129.6
Ar
and 134.0 (2CH ), 138.3 and 140.8 (2Cq), 151.2 (Cq),
Robabeh Baharfar https://orcid.org/0000-0002-8215-1851
Daryoush Zareyee https://orcid.org/0000-0001-9405-5683
Ar
1
57.9, 163.1 and 174.6 (3COamide), 190.4 (COketone); MS,
+
●
m/z: 441 (M ).
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1
.5.10 | 6‐(4‐fluorobenzoyl)‐1,3‐Dimethyl‐
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