Magnetic Fe3O4@SiO2 Core–Shell Nanoparticles Functionalized with Sulfamic Acid Polyamidoamine (PAMAM) Dendrimer for the Multicomponent Synthesis of Polyhydroquinolines and Dihydro-1H-Indeno[1,2-b] Pyridines

Full text of DOI:10.1080/00304948.2021.1957644

Organic Preparations and Procedures International
The New Journal for Organic Synthesis
ISSN: (Print) (Online) Journal homepage: https://www.tandfonline.com/loi/uopp20
Magnetic Fe3O4@SiO2 Core–Shell Nanoparticles
Functionalized with Sulfamic Acid Polyamidoamine
(PAMAM) Dendrimer for the Multicomponent
Synthesis of Polyhydroquinolines and Dihydro-1H-
Indeno[1,2-b] Pyridines
Soheila Sargazi Karbasaki, Ghodsieh Bagherzade, Behrooz Maleki & Milad
Ghani
To cite this article: Soheila Sargazi Karbasaki, Ghodsieh Bagherzade, Behrooz Maleki & Milad
Ghani (2021): Magnetic Fe3O4@SiO2 Core–Shell Nanoparticles Functionalized with Sulfamic Acid
Polyamidoamine (PAMAM) Dendrimer for the Multicomponent Synthesis of Polyhydroquinolines
and Dihydro-1H-Indeno[1,2-b] Pyridines, Organic Preparations and Procedures International, DOI:
10.1080/00304948.2021.1957644
To link to this article: https://doi.org/10.1080/00304948.2021.1957644
Published online: 04 Aug 2021.
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ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
https://doi.org/10.1080/00304948.2021.1957644
OPPI BRIEF
Magnetic Fe3O4@SiO2 Core–Shell Nanoparticles
Functionalized with Sulfamic Acid Polyamidoamine
(PAMAM) Dendrimer for the Multicomponent Synthesis of
Polyhydroquinolines and Dihydro-1H-Indeno[1,2-b] Pyridines
Soheila Sargazi Karbasakia, Ghodsieh Bagherzadea, Behrooz Malekib , and Milad
Ghanic
b
aDepartment of Chemistry, Faculty of Sciences, University of Birjand, Birjand, Iran; Department of
c
Chemistry, Hakim Sabzevari University, Sabzevar, Iran; Department of Analytical Chemistry, Faculty of
Chemistry, University of Mazandaran, Babolsar, Iran
ARTICLE HISTORY Received 4 November 2020; Accepted 16 May 2021
In recent years, the development of environmentally benign catalysts and conditions has
been one of the most important goals in the synthesis of widely used organic com-
pounds.1–3 Magnetic nanoparticles (MNPs) are promising materials for researchers due
to their strong magnetic properties, small size, high surface area, low-cost synthesis and
biocompatibility.4–5 MNPs have been used in a broad array of applications such as
catalysis,6 drug delivery,7 magnetic resonance imaging,8 sensors,9 nonlinear optics,10 and
gene therapy.11 Furthermore, Fe3O4 nanoparticles enable encapsulation or immobiliza-
tion of molecules such as dendrimers, proteins, and enzymes.12
Dendrimers are size- and shape-controlled macromolecules consisting of branches
connected to a central core. Dendrimers immobilized on magnetic nanoparticles have
been investigated intensively by our group and by other groups and have been used in
several applications.13–19 These catalytic materials are highly efficient in terms of reactiv-
ity and selectivity and are easily recyclable.
Multicomponent reactions (MCRs) have become powerful tools in organic, combina-
torial and medicinal chemistry, and have attracted much attention from synthetic
organic chemists because they can form complex molecules with a diverse range of
functionality from readily available starting materials.20–22
Polyhydroquinolines and dihydro-1H-indeno[1,2-b] pyridines are an important class of
fused heterocycles due to their broad range of potential biological activities, as well as their
importance in the preparation of drug molecules.23 Synthetic strategies mediated through the
use of variable catalytic systems have been reported in the literature for the synthesis of these
compounds including: Co3O4-CNTs,24 lanthanum chloride heptahydrate (LaCl3ꢀ7H2O),25 p-
TSA,26 scolecite,27 hafnium(IV)bis(perfluorooctanesulfonyl)imide,28 PPA-SiO2,29 TiO2 NPs,30
Fe3O4@chitosan,31 Fe3O4-SA-PPCA,32 MoO3-SiO2,33 1,3-di-bromo/chloro)-5,5-dimethylhydan-
toin (DBH or DCH),34 the polymeric catalyst [poly(AMPS-co-AA)],35 Fe3O4@SiO2/ZnCl2,36
CONTACT Behrooz Maleki
b.maleki@hsu.ac.ir
Department of Chemistry, Hakim Sabzevari University,
Sabzevar, Iran
Supplemental data for this article can be accessed online at https://doi.org/10.1080/00304948.2021.1957644.
ß 2021 Taylor & Francis Group, LLC

2
S. S. KARBASAKI ET AL.
Scheme 1. Synthesis of polyhydroquinoline and dihydro-1H-indeno[1,2-b] pyridines catalyzed by
Fe3O4@SiO2@PAMAM(G2)-SO3H.
magnetic Fe3O4 supported glutathione,37 L-proline,38 Yb(OTf)3 or Sc(OTf)3,39 and 2,2,2-tri-
fluoroethanol (TFE),40 MMWCNTs-D-(CH2)4-SO3H,41 the acidic ionic liquid [H-NP]HSO4
(H-NPBS),42 and tribromo melamine (TBM).43
Unfortunately, many of these synthetic methods, have limitations such as harsh reac-
tion conditions, long reaction times, low yields, or the use of hazardous solvents. In
order to overcome these limitations and in continuation of our research on heterocycle
synthesis,44–48 we became interested in using magnetic Fe3O4@SiO2 core–shell nanopar-
ticles functionalized with sulfamic acid polyamidoamine (PAMAM) dendrimer
[Fe3O4@SiO2@PAMAM(G2)-SO3H]17,18 for the synthesis of polyhydroquinolines and
dihydro-1H-indeno[1,2-b] pyridines (Scheme 1).
We now describe a method based on combining the features of magnetic nanopar-
ticles and dendrimers. The greater selectivity, large surface-to volume ratios, enhanced
reaction rates, simple workup (using an external magnet) and recyclability of the cata-
lyst are features that make magnetic Fe3O4@SiO2 core–shell nanoparticles functionalized
with sulfamic acid polyamidoamine (PAMAM) dendrimer [Fe3O4@SiO2@PAMAM(G2)-
SO3H] an attractive alternative heterogeneous catalyst. The silica coating can prevent
aggregation and improve the properties of magnetic nanoparticles due to its biocom-
patibility, inertness, and chemical stability. We have demonstrated this by growing a
polyaminoamido (PAMAM) dendron on nanomagnetic (Fe3O4) coated by a silica shell
(Fe3O4@SiO2-PAMAM-G2).17 Amino groups at the terminus of the polyamidoamine
(PAMAM) dendrimer were then sulfonated with chlorosulfonic acid, giving
Fe3O4@SiO2@PAMAM(G2)-SO3H.18
Chlorosulfonic acid is very hazardous to both human health and the environment,
since it is a corrosive liquid acid with high activity. This substance may be fatal if
inhaled, absorbed through the skin or swallowed and can cause eye damage and skin
burns. This strong oxidizer reacts violently with water to form the toxic gases hydrogen
chloride and sulfur dioxide,49 and contact with other materials may cause a fire.
Preparation of heterogeneous chlorosulfonic acid by functionalization of polyamido-
amine (PAMAM) dendrimer immobilized in nano magnetic particles is a suitable solu-
tion for safe use of this active and dangerous acid. Consequently, we were aiming to
develop an immobilized version of this acid, which should be readily accessible, robust

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
3
Table 1. Optimization of reaction conditions.
Entry
Catalyst (g)
Conditions
Time (min)
Yielda (%)
1
2
3
4
5
6
7
8
Fe3O4@SiO2@PAMAM(G2)-SO3H (0.05 g)
Fe3O4@SiO2@PAMAM(G2)-SO3H (0.05 g)
Fe3O4@SiO2@PAMAM(G2)-SO3H (0.05 g)
Fe3O4@SiO2@PAMAM(G2)-SO3H (0.05 g)
Fe3O4@SiO2@PAMAM(G2)-SO3H (0.05 g)
Fe3O4@SiO2@PAMAM(G2)-SO3H (0.04 g)
Fe3O4@SiO2@PAMAM(G2)-SO3H (0.03 g)
Fe3O4 (0.05 g)
Solvent-free/110 ꢁC
Solvent-free/100 ꢁC
Solvent-free/120 ꢁC
Ethanol (0.1 ml)/reflux
Methanol (0.1 ml)/reflux
Solvent-free/110 ꢁC
Solvent-free/110 ꢁC
Solvent-free/110 ꢁC
Solvent-free/110 ꢁC
Solvent-free/110 ꢁC
Solvent-free/80 ꢁC
Solvent-free/110 ꢁC
10
10
10
10
10
10
10
20
20
20
20
60
95
86
95
70
60
85
90
34
40
46
51
28
9
Fe3O4@SiO2 (0.05 g)
10
11
12
Fe3O4@SiO2@PAMAM(G2) (0.05 g)
ClSO3H (0.1 mL)b
c
–
aIsolated yield.
bThe ClSO3H was added dropwise to the reaction mixture in 2 min.
cThis reaction was carried out in the absence of Fe3O4@SiO2@PAMAM(G2)-SO3H.
and recyclable. Herein, we show how PAMAM dendrimer, with repeating amine/amide
branches as catchable sites of sulfonic acid groups, can be used as an attractive trans-
former of homogeneous to heterogeneous acidic catalysts.
In the present research, the catalytic activity of Fe3O4@SiO2@PAMAM(G2)-SO3H was
evaluated for the one-pot synthesis of polyhydroquinoline and dihydro-1H-indeno[1,2-
b] pyridine derivatives via a four-component reaction of aldehydes, ammonium acetate,
and ethyl acetoacetate with cyclic 1,3-dicarbonyl compounds (dimedone or
1,3-indandione).
In our preliminary studies, we optimized temperature, solvent, and amount of catalyst
using benzaldehyde (1 mmol, 0.106 g), dimedone (1 mmol, 0.140 g), ethyl acetoacetate
(1.2 mmol, 0.156 g), ammonium acetate (5 mmol, 0.385 g), and Fe3O4@SiO2@PAMAM
(G2)-SO3H as catalyst. The best conditions for this reaction were 0.05 g of catalyst under
ꢁ
solvent-free conditions at 110 C (Table 1, entry 1). We also performed the reaction in
the presence of Fe3O4, Fe3O4@SiO2, Fe3O4@SiO2@PAMAM(G2), and ClSO3H separ-
ately, but the results were not satisfactory (Table 1, entries 8-11). We did the reaction
in the absence of catalyst, and again the results were not acceptable (Table 1, entry 1ꢁ2).
Thus, we found that the optimal conditions for this reaction were heating at 110 C
using 0.05 g of Fe3O4@SiO2@PAMAM(G2)-SO3H catalyst (entry 1).
In order to demonstrate the generality and efficacy of the catalyst, ammonium acet-
ate, ethyl acetoacetate, and different kinds of aldehydes, containing either electron-
donating or electron-withdrawing groups, were reacted with dimedone or 1,3-indan-
dione; the results are summarized in Table 2. These reactions were very efficient and
the desired products were obtained in very good to excellent yields (88–95%) in rela-
tively short reaction times, without formation of by-products. Yields were uniformly
high, and the process does not appear to be especially sensitive to the electronic nature
of the substituent groups.
For the one-pot synthesis of polyhydroquinolines, the expected compounds (6a-h)
were obtained in high yields as the major products. For example, none of the corre-
sponding by-products (8a) and 2,2’-phenylmethylene bis(3-hydroxy-5,5-dimethyl-2-
cyclohexen-1-one) (9a) were formed (Figure 1).48
The recovery and reusability of catalysts are very important for commercial and
industrial purposes as well as for green chemistry considerations. The recovery and

4
S. S. KARBASAKI ET AL.
Table 2. Representative polyhydroquinolines and dihydro-1H-indeno[1,2-b] pyridines.
mp (ꢁC)
Entry
1
Products
Time (min)
10
Yield (%)
95
Found
Lit.
204-20636
202-204
(6a)
2
15
91
243-245
242-24436
(6b)
3
15
92
252-254
251-25236
(6c)
4
20
91
232-234
231-23436
(6d)
5
30
89
259-261
258-26036
(6e)
(continued)

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
5
Table 2. Continued.
mp (ꢁC)
Entry
6
Products
Time (min)
20
Yield (%)
88
Found
Lit.
254-256
253-25536
(6f)
7
15
94
178-179
178-17936
(6g)
8
30
88
192-194
193-19536
(6h)
9
10
95
220-221
218-22042
(7a)
10
10
91
215-217
210-21338
(7b)
(continued)

6
S. S. KARBASAKI ET AL.
Table 2. Continued.
mp (ꢁC)
Entry
11
Products
Time (min)
10
Yield (%)
94
Found
Lit.
177-179
176-17842
(7c)
12
20
90
196-198
198-19939
(7d)
13
15
91
211-213
212-21442
(7e)
14
15
90
161-163
160-16241
(7f)
reusability of Fe3O4@SiO2@PAMAM(G2)-SO3H was investigated in the sequential reac-
tion of benzaldehdye (1 mmol, 0.106 g), ethyl acetoacetate (1.2 mmol, 0.156 g), ammo-
nium acetate (5 mmol, 0.385 g), dimedone (1 mmol, 0.140 g) and the catalyst (0.05 g)

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
7
under solvent-free conditions at 110 ꢁC. The catalyst could be reused at least five times
without any significant loss in product yield (95%, 93%, 92% 90% and 87% in respective
runs).
In order to further demonstrate the efficiency of this method, Table 3 compares the
results of the synthesis of 6g and 7a with various catalysts. It can be concluded from
this table that the Fe3O4@SiO2@PAMAM(G2)-SO3H catalyst can be considered as one
of the best catalysts for these reactions because of the short reaction times, simple con-
ditions, and environmental friendliness.
We performed a hot filtration test. For this purpose, Fe3O4@SiO2@PAMAM(G2)-
SO3H (0.05 g) was added to a mixture of benzaldehyde (1 mmol, 0.106 g), ethyl acetoa-
cetate (1.2 mmol, 0.156 g), ammonium acetate (5 mmol, 0.385 g), and dimedone
(1 mmol, 0.140 g) in a 10 mL flask at room temperature, which was subsequently stirred
at 110 ꢁC for 5 min. At this step, the catalyst was separated from the reaction mixture
by the use of an external magnetic field. Then, the reaction proceeded for another
5 min under the same conditions. No increase in the amount of the product was
observed, which suggests that the leaching of sulfonic acid is low and the prepared cata-
lyst is stable. This result was confirmed by the recyclability investigations of the catalyst.
In summary, we have studied the synthesis of polyhydroquinoline and dihydro-1H-
indeno[1,2-b] pyridine derivatives using Fe3O4@SiO2@PAMAM(G2)-SO3H as a nano-
magnetic catalyst. This method has several advantages over the previous methods,
including high catalytic activity, generality, high yields, recyclability, short reaction
times, a simple experimental set-up, and an easy work-up procedure. We are continuing
to investigate the use of the title catalyst in further applications.
Experimental section
All reagents were obtained from commercial sources. The measurements of melting
points were performed using a Stuart BI Branstead Electrothermal IA9200 apparatus
and are uncorrected. A Shimadzu 435-U-04 spectrophotometer (KBr) was used for
1
recording FT-IR spectra. H NMR spectra were obtained using a Bruker 300 MHz spec-
trometer in DMSO-d6 or CDCl3 using TMS as the internal reference. The catalyst was
prepared according to the method previously described (see also Supplementary
Materials, Figures S1-S4).17,18
Preparation of Fe3O4@SiO2@PAMAM(G2)-SO3H
The Fe3O4@SiO2@PAMAM(G2)-SO3H was prepared according to the method previ-
ously described.17 Briefly, Fe3O4@SiO2@PAMAM(G2) (1.5 g) was sonicated in dry
dichloromethane for 20 min. The chlorosulfonic acid (CAUTION! 3.5 g, 30 mmol) was
added drop by drop over a period of 50 min at room temperature. After the complete
addition, the stirring was continued over a period of 8 h. The Fe3O4@SiO2@PAMAM
(G2)-SO3H catalyst was separated using an external magnet. Then, it was washed with
dichloromethane (2 X 10 ml), ethanol (2 X 10 ml), and acetone (2 X 10 ml). Finally, it
ꢁ
was dried in an oven for 7 h at 70 C to give the desired Fe3O4@SiO2@PAMAM(G2)-
SO3H catalyst.

8
S. S. KARBASAKI ET AL.
Figure 1. Product formation.
Table 3. Comparison of Fe3O4@SiO2@PAMAM(G2)-SO3H with some reported catalysts for synthesis of
polyhydroquinoline and dihydro-1H-indeno[1,2-b] pyridine derivatives.
Compounds
Conditionsref
Time (min)
Yield (%)
Fe3O4@SiO2@PAMAM(G2)-SO3H/solvent-free/
110 ˚C (present work)
15
94
LaCl3ꢀ7H2O /EtOH/rt25
180
120
60
79
85
87
95
90
80
92
86
93
86
95
p-TSA/ EtOH/rt26
Scolecite/EtOH/reflux27
Hf(NPf2)4/C10F18/60 ꢁC28
PPA-SiO2/solvent-free/80 ꢁC29
MoO3-SiO2/solvent-free/120 ꢁC33
DCH/solvent-free/130 ꢁC34
poly(AMPS-co-AA)/solvent-free/120 ꢁC35
Fe3O4@SiO2/ZnCl2/solvent-free/110 ꢁC36
nano-FGT/solvent-free/110 ꢁC37
120
55
(6g)
35
35
30
30
40
Fe3O4@SiO2@PAMAM(G2)-SO3H/solvent-free/
110 ꢁC (present work)
10
L-proline/water/reflux38
60
180
8
95
95
90
90
93
Yb(OTf)3/EtOH/us, rt39
TFE/rt40
HNPBS/solvent-free/rt42
TBM/solvent-free/70 ꢁC43
15
12
(7a)
General procedure for synthesis of polyhydroquinolines (6a-h) and dihydro-1H-
indeno[1,2-b] pyridines (7a-f) using Fe3O4@SiO2@PAMAM(G2)-SO3H
Fe3O4@SiO2@PAMAM (G2)-SO3H (0.05 g) was added to a mixture of aldehyde
(1 mmol), ethyl acetoacetate (1.2 mmol, 0.156 g), ammonium acetate (5 mmol, 0.385 g),
and 1,3-dicarbonyl compound [dimedone or 1,3-indandione (1 mmol, 0.140 or 0.146 g)]

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
9
ꢁ
in a 10 mL flask at room temperature. The temperature was then raised to 110 C and
maintained for the appropriate time (see Table 2) with stirring. The reaction progress
was monitored by TLC (n-hexane:ethyl acetate, 2:1). After completion of the reaction
2 mL hot ethanol was added to the reaction mixture, and stirring was continued for
2 minutes. The Fe3O4@SiO2@PAMAM(G2)-SO3H catalyst was separatedꢁusing an exter-
nal magnet, then washed with ethanol and acetone, and dried at 60 C for 3 h. The
resulting mixture was poured into crushed ice, and the final products (6a-h and 7a-f)
were obtained through filtration and recrystallization from ethanol. All of the products
of this study were known compounds, identified by matching their melting points with
the literature values in the references cited in Table 2. Representative spectroscopic data
are given below for 6b and 7a.
Larger Scale Preparation of 6a
Fe3O4@SiO2@PAMAM(G2)-SO3H (2.5 g) was added to a mixture of benzaldehyde
(50 mmol, 5.3 g,), ethyl acetoacetate (60 mmol, 9.36 g), ammonium acetate (250 mmol,
19.25 g), and dimedone (50 mmol, 7.00 g) in a 100 mL flask at room temperature. The
ꢁ
temperature was then raised to 110 C and maintained for 20 min with stirring. The
reaction progress was monitored by TLC (n-hexane:ethyl acetate, 2:1). After completion
of the reaction 40 mL hot ethanol was added to the reaction mixture, and stirring was
continued for 5 minutes. The nanomagnetic catalyst was separated from the reaction
mixture as described above and the product isolated as described above and recrystal-
lized from 96% ethanol (80 ml) to afford 88% of ethyl-1,4,7,8-tetrahydro-2,7,7-trimethyl-
4-(phenyl)5-(6H)-oxoquinoline-3-carboxylate (6a).
Ethyl-1,4,7,8-tetrahydro-2,7,7-trimethyl-4-(4-chlorophenyl)5-(6H)-oxoquinoline-3-
carboxylate (6b)
IR (KBr, disc, cmꢂ1): 3275, 3194, 3080, 2967, 1710, 1644, 1610, 1490, 1394, 1280, 790;
1H-NMR (300 MHz, DMSO-d6): d 0.94 (s, 3H), 1.06 (s, 3H), 1.19 (t, J ¼ 7.1 Hz, 3H),
2.14–2.36 (m, 4H), 2.36 (s, 3H), 4.07 (q, J ¼ 7.1 Hz, 2H), 5.04 (s, 1H), 6.12 (brs, 1H,
NH), 7.16 (d, J ¼ 8.4 Hz, 2H), 7.26 (d, J ¼ 8.4 Hz, 2H); 13C-NMR (75 MHz, DMSO-d6):
d 14.21, 19.46, 27.11, 29.43, 32.72, 36.21, 41.10, 50.66, 59.92, 105.76, 111.90, 128.00,
129.45, 131.6, 143.61, 145.56, 148.12, 167.22, 195.50.
2-Methyl-4-phenyl-5-oxo-4,5-dihydro-1H-indeno-[1,2-b]pyridine-3-carboxylic acid
ethyl ester (7a)
IR (KBr, disk, cmꢂ1): 3252, 2960, 1702, 1664, 1552, 1390, 1210, 780; 1H-NMR
(300 MHz, DMSO-d6) d 1.11 (t, 3H), 2.42 (s, 3H), 4.05 (q, 2H), 4.75 (s, 1H), 6.88 (s,
1H, NH), 7.14–7.30 (m, 5H), 7.42–7.66 (m, 4H); 13C-NMR (75 MHz, DMSO-d6) d
14.01, 18.13, 35.94, 51.02, 105.15, 109.07, 118.02, 121.34, 127.87, 129.09, 130.36, 131.04,
132.76, 133.62, 136.21, 144.77, 145.63, 154.08, 168.21, 191.53.

10
S. S. KARBASAKI ET AL.
Acknowledgments
The authors thank the Research Council of Hakim Sabzevari University, the University of
Birjand, and the University of Mazandaran for partial support of this work.
ORCID
Behrooz Maleki
Milad Ghani
http://orcid.org/0000-0002-0322-6991
http://orcid.org/0000-0003-1210-1856
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