Dendrimer-Functionalized Magnetic Graphene Oxide for Knoevenagel Condensation

Full text of DOI:10.1080/00304948.2021.1875799

Organic Preparations and Procedures International
The New Journal for Organic Synthesis
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Dendrimer-Functionalized Magnetic Graphene
Oxide for Knoevenagel Condensation
Behrooz Maleki, Fatemeh Taheri, Reza Tayebee & Fatemeh Adibian
To cite this article: Behrooz Maleki, Fatemeh Taheri, Reza Tayebee & Fatemeh Adibian (2021)
Dendrimer-Functionalized Magnetic Graphene Oxide for Knoevenagel Condensation, Organic
Preparations and Procedures International, 53:3, 284-290, DOI: 10.1080/00304948.2021.1875799
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ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
021, VOL. 53, NO. 3, 284–290
2
https://doi.org/10.1080/00304948.2021.1875799
EXPERIMENTAL PAPER
Dendrimer-Functionalized Magnetic Graphene Oxide for
Knoevenagel Condensation
a
a
a
b
Behrooz Maleki
, Fatemeh Taheri , Reza Tayebee
, and Fatemeh Adibian
a
b
Department of Chemistry, Hakim Sabzevari University, Sabzevar, Iran; School of Chemistry, Damghan
University, Damghan, Iran
ARTICLE HISTORY Received 14 June 2020; Accepted 30 September 2020
A great deal of attention has been paid to developing methods for heterogenizing
homogeneous catalysts in order to combine the advantages of both homogeneous and
1
heterogeneous catalysis. Among these methods, the binding of catalysts to organic
2
3
polymer solids or inorganic solids is widely used. Although the heterogenized catalysts
can be recycled and easily separated from the reaction mixtures, they are significantly
less reactive and selective than their homogeneous counterparts. For this reason, there
is a need to find new methods and strategies in order to overcome these limitations.
Graphene oxide (GO) and functionalized GOs are suitable for achieving this purpose.
GO has a large amount of functional groups on its basal plane, and these allow for the
4–6
modification of GO for further applications.
The large surface area and functional
groups act as active sites. GO is a suspension in pure water but generally aggregates in
7
salt solutions or in biological solutions. To overcome this problem and also to permit
easy separation by an external magnet, magnetic nanoparticles have been used.
Magnetic nanoparticles (MNPs) such as magnetite (Fe O ) are of much current interest
3
4
because of their magnetic and electrical properties, high specific surface area, unique
8
–10
catalytic powers and wide applications.
Dendrimers are a comparatively new class of polymeric materials. They are highly
branched, monodisperse macromolecules. The structure of these materials has a great
impact on their physical and chemical properties. As a result of their unique character-
istics, including enormous surface areas in relation to volume, the presence of internal
cavities and the possibility of encapsulating guest molecules, dendrimers are suitable for
a wide range of biomedical and industrial uses. For example, polyamidoamine
1
1–14
(PAMAM), has been beneficially applied.
We now describe a useful synthetic organic method based on combining the features
of magnetic nanoparticles, GO and dendrimers. The objective of this strategy is to hom-
ogenize a heterogeneous catalyst. Thus we sought to: (i) use magnetic nanoparticles to
minimize the support for the immobilization of the catalyst, while at the same time
keeping it easily separable; and (ii) use the dendrimerization process to produce organic
arms on the support. The latter action will enhance the compatibility of the material
with the medium, allow it to mimic real homogeneous catalysts and promote our
CONTACT Behrooz Maleki
b.maleki@hsu.ac.ir
Department of Chemistry, Hakim Sabzevari University,
Sabzevar, Iran
ß 2021 Taylor & Francis Group, LLC

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
285
a
Table 1. Optimization of reaction conditions for 3a.
Entry
Catalyst (g)
Conditions
Time (min)
Yield (%)
ꢀ
1
2
3
4
5
6
7
8
9
Fe
Fe
Fe
Fe
Fe
Fe
Fe
Fe
Fe
3
3
3
3
3
3
3
3
3
O
O
O
O
O
O
O
O
O
4
4
4
4
4
4
4
4
4
@GO@PAMAM (G
@GO@PAMAM (G
@GO@PAMAM (G
@GO@PAMAM (G
@GO@PAMAM (G
@GO (0.008)
2
2
2
2
2
) (0.008)
) (0.007)
) (0.008)
) (0.008)
) (0.008)
Solvent-free/60 C
20
20
20
20
60
20
20
20
20
30
95
85
82
92
42
20
75
40
32
ꢀ
Solvent-free/60 C
ꢀ
Solvent-free/50 C
ꢀ
Solvent-free/70 C
ꢀ
Solvent-free/25 C
ꢀ
Solvent-free/60 C
ꢀ
@GO@PAMAM (G
@GO@PAMAM (G
@GO@PAMAM (G
1
2
2
) (0.008)
) (0.008)
) (0.008)
Solvent-free/60 C
ꢀ
Water/60 C
ꢀ
Ethanol/60 C
b
ꢀ
c
1
1
–
Solvent-free/60 C
–
a
Reaction conditions: benzaldehyde (1 mmol) and malononitrile (1.2 mmol).
This reaction was carried out in the absence of Fe O @GO@PAMAM (G ).
3 4 2
b
c
No product 3a observed.
Scheme 1. Synthesis of benzylidenemalononitrile derivatives catalyzed by Fe O @GO@PAMAM (G ).
3
4
2
synthetic purpose. We thus grew a PAMAM dendron on nanomagnetite Fe O @GO.
3
4
The preparation of the Fe O @GO@PAMAM (G ) was accomplished according to a
3
4
2
1
5
procedure described in the literature.
The Knoevenagel condensation of aldehydes with compounds containing activated
methylene groups is an important reaction for C ¼ C bond formation in organic com-
pounds. Because of its simplicity, economy and efficiency, this process is frequently
1
6–21
used,
exchanged NaY zeolite [RE(72%)NaY],
and we may note the use of numerous catalysts, including rare-earth (RE)
22
cetyltrimethyl ammonium bromide
2
3
24
2þ
25
(
CTMAB), MgO/ZrO2, Zn exchanged Hß (Znß), polyvinyl chloride supported
tetraethylenepentamine (PVC-TEPA), Na S/Al O , magnesium fluoride, Ni–SiO2,
ceria-zirconia (C/Z-30/70), La O –MgO/KOH, guanidine supported on magnetic
nanoparticles Fe O (Fe O @guanidine), BEA or TS-1 or CuBTC or FeBTC, gallium
2
6
27
28
29
2
2 3
31
3
0
2
3
3
2
33
3
4
3 4
3
4
35
chloride (GaCl3),
polyvinyl amine coated Fe O @SiO (Fe O @SiO -PVAm),
3 4 2 3 4 2
3
6
Fe O @UiO-66-NH ,
N-(3-trimethoxysilylpropyl)diethylenetriamine)
coated
3
4
2
7
3
3 4 2 3 4 3 4 2
38
(
Fe O @SiO -3N), Fe O @P4VP@ZIF-8, magnetic Fe O @SiO @Ni-Zn-Fe layered
39
40
double hydroxide (LDH) (Fe O @SiO @Ni-Zn-Fe LDH), and fiber (PAN F-3).
3
4
2
P
In furtherance of our studies of organic reactions in the presence of benign heteroge-
4
1–50
neous and homogeneous catalysts,
we now demonstrate the preparation of benzyli-
denemalononitrile (BMN) derivatives by Knoevenagel condensation of benzaldehydes
(1 mmol) and malononitrile (1.2 mmol) using [Fe O @GO@PAMAM (G )] as catalyst
3 4 2
(Scheme 1).

2
86
B. MALEKI ET AL.
Table 2. Preparation of benzylidenemalononitrile derivatives (3a-j).
ꢀ
m.p ( C)
Entry
Product (3a-j)
Time (min)
20
Yield (%)
95
Found
80-82
Reported
2
3
3a
3b
3c
81-82
2
2
7
7
30
30
95
90
102-104
159-161
101-103
161-162
4
0
3
3
d
e
15
15
86
80
103-105
79-80
102-104
2
3
7
80-81
84-86
2
3
3
f
35
30
82
90
85-87
2
3
g
164-166
162-163
4
2
0
3
3
3
h
i
40
40
90
90
151-152
178-180
148-150
179-180
2
7
3
j
60
85
136-137
137-138
To define the best conditions for this reaction, we optimized the type and amount of
catalyst, temperature and solvent. Our study started by using benzaldehyde (1 mmol)
and malononitrile (1.2 mmol) in a model reaction. Our results on optimization are
shown in Table 1. The best results are represented by Entry 1, when the model reaction
was carried out in the presence of Fe O @GO@PAMAM (G ) (0.008 g) under solvent-
3
4
2
ꢀ
free conditions at 60 C.
To probe the generality of this reaction we reacted malononitrile with ten aryl alde-
hydes substituted with both electron-withdrawing and electron-donating groups, includ-
ing aldehydes with ortho substituents. The experiments were repeated three times for

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
287
Figure 1. Reusability of Fe O @GO@PAMAM (G ).
3
4
2
each aldehyde and the average yields are reported in Table 2. The products were formed
in high to excellent yields (see Experimental section; mean yield 88%).
The recyclability of the Fe O @GO@PAMAM (G ) was checked in the model reac-
3
4
2
tion under optimized conditions. After completing the reaction, 1 mL ethanol was added
to the reaction mixture and then the catalyst was easily separated using an external
magnet. Fe O @GO@PAMAM (G ) was reused in the model reaction after washing
3
4
2
with acetone and deionized water and drying. As shown in Figure 1, the nanocatalyst
could be reused in four reaction runs before considerable loss in activity was observed.
Table 3 shows the efficiency of the present procedure for the synthesis of 2-benzyli-
dene malononitrile (3a), compared with previously reported procedures in the literature.
The data suggest that Fe O @GO@PAMAM (G ) stands among the best catalysts and
3
4
2
has the desirable attributes of high yield, short reaction time and the avoidance
of solvents.
In conclusion, our work illustrates the advantages of heterogenizing homogeneous
catalysts in order to improve synthetic organic preparations. The efficiency of
Fe O @GO@PAMAM (G ) as a reusable and highly effective catalyst was illustrated for
3
4
2
the synthesis of benzylidenemalononitrile derivatives through the Knoevenagel reaction.
Over-all, this synthetic approach provides excellent yields and short reaction times.
Among the green characteristics of this method are low waste generation, the avoidance
of solvent, simple work-up, easy separation and reusability of catalyst. We hope that
our catalyst can be applied for the promotion of a wide range of Knoevenagel reactions
and other related reactions.
Experimental section
All reagents were obtained from commercial sources. Melting points were determined
on an Electrothermal 9200 apparatus and are uncorrected. IR spectra were recorded at
room temperature on a Shimadzu 435-U-04 spectrophotometer using KBr disks and are
ꢁ
1
1
reported in cm . A Bruker DRX-400 Avance spectrometer was used for recording H
1
3
and C NMR spectra at 400 MHz and 100 MHz in CDCl or DMSO-d using tetrame-
3
6
thylsilane as an internal standard. First order aromatic couplings were within the
expected range and are not enumerated. The catalyst was prepared according to the
1
5
method previously described.

2
88
B. MALEKI ET AL.
Table 3. Comparison of methods for the synthesis of 2-benzylidene malononitrile (3a).
Time
(min)
Conditions
@GO@PAMAM (G )/Solvent-free/60 C
Yield (%)
ꢀ
Fe
3
O
4
2
20
720
90
20
360
60
95
78
91
93
16
75
90
93
100
82
73
93
99
92
22
RE(72%)NaY/CH
3
CN/rt
2
3
CTMAB/H
MgO/ZrO
Znß/Solvent-free/140 C
2
O/rt
ꢀ
24
2
/Solvent-free/60 C
ꢀ
25
2
6
PVC-TEPA/EtOH/reflux
Na S/Al /CH Cl /reflux
MgF /EtOH/rt
Ni–SiO /Toluene/reflux3
C/Z-30/70/EtOH/reflux
27
2
2
O
3
2
2
20
2
8
(
3a)
2
150
900
50
60
12
120
90
2
9
2
0
ꢀ
36
Fe
Fe
Fe
Fe
3
O
3
O
3
O
3
O
4
4
4
4
@UiO-66-NH
@SiO -3N/Water/75 C
@P4VP@ZIF-8/Toluene/23 C
2
-3/DMF/80 C
ꢀ
37
2
ꢀ
38
4
0
2
@SiO @Ni-Zn-Fe/EtOH/reflux
General procedure for synthesis of benzylidenemalononitrile derivatives (3a-j)
catalyzed by Fe O @GO@PAMAM (G )
3
4
2
Fe O @GO@PAMAM (G ) (0.008 g) was added to a mixture of the benzaldehyde
3
4
2
ꢀ
(
1 mmol) and malononitrile (1.2 mmol). The mixture was heated at 60 C on an oil bath
under solvent-free conditions for the appropriate time (Table 2). The progress of reac-
tion was monitored by TLC (silica gel; n-hexane:ethyl acetate, 4:1). After completion of
the reaction, 1 mL ethanol was added to the mixture and then the nanocatalyst was eas-
ily separated using an external magnet. The resulting mixture was poured into crushed
ice to precipitate the product. The product was filtered off and was recrystallized from
ethanol (96%) to get the respective pure 2-benzylidenemalononitrile derivatives (3a-j).
All of the compounds in this study were known and were identified by matching their
melting points with the literature values cited in Table 2. For the sake of completeness,
1
13
representative IR, H-NMR and C-NMR are provided below for compounds 3d
and 3h.
2
-(3-Methoxybenzylidene)malononitrile (3d)
ꢁ
1 1
IR (KBr) 3039, 2217, 1575, 1470, 1249, 756, 613 cm ; H-NMR (DMSO-d , 400 MHz)
6
d: 8.47 (s, 1H, CH), 7.95-7.97 (d, 1H, CH, aromatic), 7.66-7.70 (d, 1H, CH aromatic),
13
7
.13-7.24 (m, 2H, 2CH aromatic), 3.906 (s, 3H, OCH3); C-NMR (DMSO-d ,100 MHz)
6
d: 159.10, 156.50, 136.99, 129.33, 120.39, 120.35, 114.88, 113.73, 112.89, 81.99, 56.52.
2
-(3-Hydroxybenzylidene)malononitrile (3h)
ꢁ
1 1
IR (KBr) 3359, 3014, 2235, 1573, 1467, 781, 673 cm ; H-NMR (DMSO-d , 400 MHz)
6
d: 8.44 (s, 1H, CH), 7.07-7.09 (d, 1H, CH aromatic), 7.35-7.43 (m, 3H, 3CH aromatic),
1
3
1
1
0.13 (s, 1H, OH); C-NMR (DMSO-d , 100 MHz) d: 162.10, 158.34, 132.86, 131.06,
6
22.50, 122.27, 116.57, 114.76, 113.66, 81.58.

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
289
Acknowledgment
The authors are grateful to the Research Council of Hakim Sabzevari University for partial sup-
port of this work.
ORCID
Behrooz Maleki
Reza Tayebee
Fatemeh Adibian
http://orcid.org/0000-0002-3740-7096
http://orcid.org/0000-0003-1211-1472
http://orcid.org/0000-0002-6365-9780
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