Synthesis of polyhydroquinolines and propargylamines through one-pot multicomponent reactions using an acidic ionic liquid immobilized onto magnetic Fe3O4as an efficient heterogeneous catalyst under solvent-free sonication

Article abstract of DOI:10.1039/d0ra04008h

A nano-sized Fe3O4-supported Lewis acid ionic liquid catalyst for the synthesis of polyhydroquinolines and propargylamines under ultrasound irradiation has been developed. LAIL&at;MNP was synthesized from imidazolium chlorozincate(ii) ionic liquid grafted onto the surface of Fe3O4 nanoparticles and evaluated by FT-IR, TGA, SEM, Raman, TEM, ICP-OES, and EDS. The multicomponent synthesis of polyhydroquinolines and propargylamines proceeded smoothly to afford the desired products in high yields. LAIL&at;MNP can be separated easily from the reaction mixture and reused for several runs without a significant degradation in catalytic activity.

Full text of DOI:10.1039/d0ra04008h

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Synthesis of polyhydroquinolines and
propargylamines through one-pot
Cite this: RSC Adv., 2020, 10, 25358
multicomponent reactions using an acidic ionic
liquid immobilized onto magnetic Fe3O4 as an
efficient heterogeneous catalyst under solvent-free
sonication†
ab
ab
ab
*
Hai Truong Nguyen,
Vy Anh Truong
and Phuong Hoang Tran
A nano-sized Fe3O4-supported Lewis acid ionic liquid catalyst for the synthesis of polyhydroquinolines and
propargylamines under ultrasound irradiation has been developed. LAIL@MNP was synthesized from
imidazolium chlorozincate(II) ionic liquid grafted onto the surface of Fe3O4 nanoparticles and evaluated
by FT-IR, TGA, SEM, Raman, TEM, ICP-OES, and EDS. The multicomponent synthesis of
polyhydroquinolines and propargylamines proceeded smoothly to afford the desired products in high
yields. LAIL@MNP can be separated easily from the reaction mixture and reused for several runs without
a significant degradation in catalytic activity.
Received 4th May 2020
Accepted 28th June 2020
DOI: 10.1039/d0ra04008h
rsc.li/rsc-advances
antagonists,21 and antidiabetic properties22 (Scheme 1). Various
methods have been developed to synthesize polyhydroquino-
lines,23–25 pyridines,26 pyridylalanines,27 pyrroles,28 furans,28 etc.
Introduction
The application of heterogeneous catalysts in organic synthesis
has attracted much attention due to the prominent features of
these catalysts, such as high efficiency, simple recovery, and
reusability.1 However, the major limitation of heterogeneous
catalysts is their low catalytic activity and selectivity because of
slow dispersibility in the solvent.2 Magnetic nanoparticles
(MNPs) are known as a new type of catalyst support because of
their easy synthesis, good stability, high surface area, and facile
separation from the reaction mixture.3 Currently, there are
many reports about the catalytic performance of Fe3O4@ZrO2/
via the multicomponent Hantzsch reaction. Recently, different
catalysts for the synthesis of PHQ from aldehydes, b-dicarbonyl
compounds, active methylene compounds, and ammonium
acetate have been reported including metal triates,29 zeolites,30
ionic liquids,31–33 nanoparticles,34–40 heterogeneous nano-
catalyst,41,42 metal halide,43–45 organic solid acid,46 enantiose-
49
lective organocatalysis,47 nanocomposites,48 Bronsted acidic.
¨
Propargylamine derivatives are widely used in the pharma-
ceutical industry (Scheme 2),50 which are known as precursors
in the formation of quinolines,51 oxazoles,52 imidazoles,53
indolizines,54 oxazolidinones,55 aza-anthraquinone,56 phenan-
throlines,57 pyrroles,58 pyrrolidines,59 dihydropyridine,60 and
pyridocoumarins.61 Moreover, some propargylamine derivatives
had been committed as energetic anti-apoptotic agents62 and
useful in treating Parkinson's disease patients.63 There were
2À
SO4 MNPs,4 Fe3O4@SiO2–SO3H MNPs,5,6 CoFe2O4@SiO2–
SO3H MNPs,7 Fe3O4@ ZrO2–Pr–SO3H MNPs,8 and CuFe2O4
@SO3H MNPs9 in organic synthesis. Recently, Lewis acidic ionic
liquids supported on magnetic nanoparticles have been exten-
sively studied in organic synthesis due to high efficiency, simple
recovery by an external magnet, excellent thermal stability, and
reuse without loss of the activity.10–14
Polyhydroquinoline heterocycles (PHQ) have received
considerable interest owing to their pharmacological activities
such as anticancer,15 antiplasmodial,16 antiatherosclerotic,17
antibacterial,18 antiproliferative,19 antimalarial,20 calcium
aDepartment of Organic Chemistry, Faculty of Chemistry, University of Science, Ho Chi
Minh City, 721337, Vietnam. E-mail: thphuong@hcmus.edu.vn
bVietnam National University, Ho Chi Minh City, 721337, Vietnam
† Electronic supplementary information (ESI) available. See DOI:
10.1039/d0ra04008h
Scheme 1 Some bioactive polyhydroquinolines.
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spectrum (ESI, Fig. S1–S4†). The amount of zinc element in
LAIL@MNP was found to be 0.3 mmol gÀ1 by ICP-MS.
Synthesis of polyhydroquinolines
The multicomponent reaction is one of the attractive tools in
the synthesis of bioactive compounds.66,67 The catalytic activity
of LAIL@MNP-catalyzed was performed the synthesis of poly-
hydroquinolines via Hantzsch reaction, four-component
condensation reactions of dimedone, ethyl acetoacetate,
ammonium acetate and aldehydes under solvent-free sonica-
tion. As shown from Table S1 (please see in ESI†), the conden-
sation reaction between benzaldehyde, dimedone, ethyl
acetoacetate, and ammonium acetate in the presence of
LAIL@NMP (15 mg) provided in 68% yield under sonication at
room temperature for 60 min (Table S1,† entry 5). Interestingly,
the excellent yield was observed when the reaction 80 ꢀC within
45 min (Table S1,† entry 9). Then, the loading of LAIL@NMP
was examined in various weights ranging from 1 mg to 20 mg,
and the best yield was attained with 15 mg of LAIL@NMP. Table
1 shows that LAIL@MNP is also a suitable catalyst for the
synthesis of polyhydroquinolines.
LAIL@NMP catalyzed the Hanzsch condensation of aldehyde
(1.0 mmol), dimedone (1.0 mmol), ethyl acetoacetate (1.0
mmol), and ammonium acetate (2.0 mmol) solvent-free soni-
cation. As shown in Table 2, the reaction was proceeded
smoothly with cyclohexanecarbaldehyde to provide the product
in 88% yield was for 45 min under sonication. Ortho- or para-
substituted benzaldehydes containing electron-poor groups
Scheme 2 Some bioactive propargylamines.
several classical methods for the preparation of propargyl-
amines, and the straightforward and efficient method was A3-
coupling from alkynes, aldehydes, and amines.64
As a continuation of previous work involving the application
of Lewis acidic ionic liquids supported onto magnetic nano-
particles in organic synthesis,65 we report herein the use of the
material as a recyclable catalyst for multicomponent reactions
in the synthesis of polyhydroquinolines through Hantzsch
condensation and propargylamines through A3-coupling reac-
tion under solvent-free sonication.
Results and discussion
Synthesis of LAIL@MNP
The LAIL@MNP was synthesized following a previously re- such as chloro and uoro exhibited weaker activity than benz-
ported procedure.65 The magnetic nanoparticle supported ionic aldehyde. For those bearing electron-rich groups such as
liquid catalyst was prepared in a few steps. MNPs were obtained methyl, methoxy, and tert-butyl at the para position, the yields
by a simple co-precipitation method in the presence of KOH were nearly equal to that of benzaldehyde. Substrates contain-
solution. Next, the imidazole chloride ionic liquid was synthe- ing o-substituted polar functional groups, such as –OH and
sized from 3-chloroethoxypropylsilane and imidazole. Then, –COOH, afforded the respective products whose yields were
imidazole-functionalized
magnetic
Fe3O4
nanoparticle 20% less than that of benzaldehyde. The method was also effi-
(IL@MNP) was reacted with ZnCl2 to afford the LAIL@MNP. cient for furan aldehydes to give the desired products in 79–89%
Characterization of the synthesized nano-Fe3O4 and yields.
LAIL@MNP was determined using Fourier transform infrared
A plausible mechanism for the synthesis of poly-
(FT-IR) spectroscopy, scanning electron microscopy (SEM), hydroquinolines using LAIL@NMP was demonstrated in
transmission electron microscopy (TEM), thermo-gravimetric Scheme 3. The zinc species of LAIL@MNP catalyst coordinated
analysis (TGA), energy dispersive spectrum (EDS), and Raman with oxygen on the carbonyl group of benzaldehyde which
Table 1 Comparative effectiveness for the four-component synthesis of polyhydroquinolines
Temperature
Entry
Catalyst
(ꢀC)
Time (h)
Yield (%)
1
2
3
4
5
6
7
8
9
10
Yb(OTf)3/EtOH (5 mol%)
p-TSA/EtOH (10 mol%)
Scolecite/EtOH (200 mg)
Hf(NPf2)4/C10H18 (1 mol%)
SSA/solvent-free (0.20 mmol, 0.08 g)
Sc(OTf)3/EtOH (5 mol%, 25 mg)
DBH/solvent-free (10 mol%)
Nano Pd-(0)/THF (2 step)
Cs2.5H0.5PW12O40/melting metal (0.01 mmol)
Present work: LAIL@MNP (15 mg), solvent-free
r.t.
r.t.
reux
60
60
5
2
0.75
3
0.75
4
0.5
4.3
0.1
0.75
90 (ref. 29)
93 (ref. 68)
93 (ref. 69)
95 (ref. 24)
92 (ref. 70)
93 (ref. 23)
90 (ref. 71)
87 (ref. 35)
92 (ref. 72)
97
r.t.
130
reux
110
80
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Table 2 The synthesis of various polyhydroquinolines using LAIL@MNP under solvent-free sonicationa
a
Aldehyde (1 mmol), ethyl acetoacetate (1.0 mmol), dimedone (1 mmol), and ammonium acetate (2.0 mmol) in the presence of LAIL@MNP (15 mg)
under solvent-free sonication. Yields are isolated yield.
enhanced the electrophilicity of carbonyl carbon, providing rise
to a better nucleophilic attack of dimedone to benzaldehyde to
produce an intermediate (A). In the second step, b-ketoester
(ethyl acetoacetate) is activated by acid catalysis with the release
of ammonia from ammonium acetate (NH4OAc) to produce
enamine (B) along with CH3COOH as a by-product. Then, the
Michael additive reaction occurs between (A) and (B), followed
by the cyclization creating intermediate (C) and (D). Finally, the
deprotonation of (D) provides the Hantzsch 1,4-
dihydropyridines.
Synthesis of propargylamines
The catalytic activity of LAIL@MNP was demonstrated through
a one-pot multicomponent reaction of phenylacetylene, piperi-
dine, and aldehydes under solvent-free sonication. The effect of
various parameters including time, temperature, amount of
catalyst, and different solvents was investigated. As can be seen
from Table S3,† the reaction of phenylacetylene (1.5 mmol),
piperidine (1.2 mmol) and benzaldehyde (1.0 mmol) was con-
ducted at 30 ꢀC or 80 ꢀC under sonication. Interestingly, a yield
of propargylamine was obtained at 80 ꢀC for 45 min in the
presence of LAIL@MNP. The excellent yield of (1,3-
diphenylprop-2-yn-1-yl)piperidine was achieved at an optimized
molar ratio 1 : 1.5 : 1.2 of benzaldehyde, phenylacetylene, and
piperidine (entry 19). The effect of catalytic loading and solvent
was also examined (entries 24–27). The results showed that the
use of 10 mg of LAIL@NMP afforded the highest yield of the
product under solvent-free sonication (Table S4†). The current
method was compared with other reports (Table 3), and
LAIL@MNP catalyst demonstrated good catalytic performance
in the preparation of propargylamines.
The scope of the substrate was explored with some aromatic
aldehydes. Under the optimal conditions, the reaction proceeded
smoothly to produce the corresponding propargylamines in good
Scheme
3 Proposed mechanism for one-pot four-component
synthesis of polyhydroquinolines.
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Table 3 Comparison methods for the preparation of propargylamines
Entry
Catalytic system
Temp. (ꢀC)
Time (h)
Yield (%)
1
2
3
4
5
6
Nano CuO/toluene (10 mol%)
Cu NPs/TiO2 (0.5% mol)
Cu2 (pip)2/toluene (0.4%)
Cu@MOF-5-C/toluene (20 mg)
Cu/Al/toluene (0.12 mmol)
90
70
110
110
100
80
5
7
2
6
22
0.75
84 (ref. 73)
90 (ref. 74)
98 (ref. 75)
96 (ref. 76)
94 (ref. 77)
85
I
Present method: LAIL@MNP (10 mg), solvent-free sonication
to excellent yields. The reaction was carried out with aryl alde-
hydes bearing an electron-donating or electron-withdrawing
group. p-Methylbenzaldehyde was proceeded smoothly under
optimized conditions. However, p-tertbutylbenzaldehyde reacted
slowly and gave the desired product in moderate yield for 60 min.
The aldehydes with halo or hydroxyl substituents in the para
position were also reactive with prolonged reaction time to 60–
70 min. The heterocyclic aldehyde, such as furfural and pyridine-
4-carbaldehyde, afforded the desired products in acceptable
yields (Table 4).
A proposed mechanism for the preparation of propargyl-
amine was demonstrated in Scheme 4. The zinc species of
LAIL@MNP catalyst coordinated with oxygen on the carbonyl
group of benzaldehyde, which enhanced the electrophilicity of
carbonyl carbon, providing rise to a better nucleophilic attack of
piperidine to benzaldehyde to produce intermediate products
(E). This intermediate product was dehydrated to form benzi-
lidenpiperidinium ion (F). Next, phenylacetylene reacted with
benzilidenpiperidinium ion (F) to form the desired product.
The recyclability of LAIL@MNP was tested in the preparation
of propargylamine under optimal reaction conditions (Fig. 1).
Scheme
propargylamines.
4
A
plausible mechanism for the synthesis of
Aer completion, the reaction mixture was diluted with ethyl
acetate (30 mL) and the LAIL@MNP was removed by an external
magnet. The LAIL@MNP was then washed with ethyl acetate (3
 3 mL), ethanol (3  3 mL), and dried in vacuo. The activity of
the recovered catalyst was assessed ve consecutive recycling
tests. The FT-IR spectrum of recovered LAIL@MNP suggested
no signicant change in functionality (please see ESI, Fig. S7†).
Table 4 LAIL@NMP-catalyzed for the synthesis of propargylaminesa
Experimental
Synthesis of LAIL@MNP
LAIL@MNP was prepared according to a procedure reported
previously in the literature.78,79 The LAIL@MNP has been
a
Reaction conditions: phenylacetylene (1.5 mmol), piperidine (1.2
mmol), and aldehyde (1.0 mmol) under solvent-free ultrasound
irradiation. The conversion was determined by GC-MS based on
aldehyde. Isolated yield was calculated based on the obtained amount
aer ash column chromatography.
Fig.
1
Recycling of LAIL@MNP for
the synthesis of
polyhydroquinolines.
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Synthesis of polyhydroquinolines
In a typical experiment, a reaction mixture of aldehyde
(1.0 mmol, 0.106 g), ethyl acetoacetate (1.0 mmol, 0.130 g),
dimedone (1.0 mmol, 0.140 g), ammonium acetate (2.ꢀ0 mmol,
0.144 g), and LAIL@MNP (15 mg) was sonicated at 80 C. Aer
completion, 10 mL ethyl acetate was added and the LAIL@MNP
was separated from an organic phase by an external magnet. The
ethyl acetate layer was extracted wit water (3 Â 15 mL), dried with
anhydrous Na2SO4 and evaporated under vacuum. The residue
was recrystallized from hot ethanol to give polyhydroquinoline.
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In a typical experiment, a reaction mixture of aldehyde (1.0 mmol,
0.106 g), phenylacetylene (1.5 mmol, 0.153 g), piperidine
(1.2 mmol, 0.102 g), and LAIL@MNP (10 mg) was sonicated at
80 ꢀC. Aer completion, 10 mL ethyl acetate was added, and the
LAIL@MNP was separated from an organic phase by an external
magnet. The organic solution was then dried with anhydrous
Na2SO4. The solvent was removed under vacuum, and the crude
product was puried through column chromatography using n-
hexane/ethyl acetate (9/1) to provide pure propargylamine.
Synthesized products were conrmed by 1H, 13C NMR, and MS.
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In summary, we have developed a recyclable and efficient
LAIL@MNP catalyst for the synthesis of polyhydroquinolines and
propargylamines. The present method demonstrated a facile and
green approach toward polyhydroquinolines and propargylamines
under ultrasound irradiation. The LAIL@MNP can be quickly
recovered and reused without a considerable decline in catalytic
activity.
Conflicts of interest
There are no conicts of interests to declare.
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Acknowledgements
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Hai Truong Nguyen acknowledges the Domestic Master/PhD
Scholarship Programme of Vingroup Innovation Foundation
(VINIF.2019.TS.20) for polyhydroquilonine derivatives synthesis
and characterization. Phuong Hoang Tran acknowledges the
Vietnam National University – Ho Chi Minh City (VNU-HCM)
through Project No. 562-2020-18-01 for catalytic investigation
for propargylamine synthesis and LAIL@MNP preparation
characterization.
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