Perlite–SO3H nanoparticles: very efficient and reusable catalyst for three-component synthesis of N-cyclohexyl-3-aryl-quinoxaline-2-amine derivatives under ultrasound irradiation

Article abstract of DOI:10.1007/s13738-018-1426-8

An efficient green approach for the synthesis of N-cyclohexyl-3-aryl-quinoxaline-2-amine derivatives, via a three-component one-pot condensation reaction of o-phenylenediamine, aromatic aldehydes and cyclohexyl isocyanide in the presence of perlite–SO₃H nanoparticles (diameter/thickness of platelets < 100?nm) under ultrasound irradiation has been demonstrated. The present method offers advantages such as shorter reaction time, easy work-up, excellent yields, recovery and reusability of catalyst. In addition, the methodology has been prosperous in getting the green chemistry purposes such as natural catalyst, using ultrasound irradiation instead of conventional heating and stirring, and a non-hazardous products in the thus combining the features of both economic and environmental advantages.

Full text of DOI:10.1007/s13738-018-1426-8

Journal of the Iranian Chemical Society
https://doi.org/10.1007/s13738-018-1426-8
ORIGINAL PAPER
Perlite–SO3H nanoparticles: very efficient and reusable catalyst
for three-component synthesis of N-cyclohexyl-3-aryl-quinoxaline-2-
amine derivatives under ultrasound irradiation
Morteza Rouhani1 · Ali Ramazani2
Received: 27 December 2017 / Accepted: 31 May 2018
© Iranian Chemical Society 2018
Abstract
An efficient green approach for the synthesis of N-cyclohexyl-3-aryl-quinoxaline-2-amine derivatives, via a three-component
one-pot condensation reaction of o-phenylenediamine, aromatic aldehydes and cyclohexyl isocyanide in the presence of
perlite–SO3H nanoparticles (diameter/thickness of platelets <100 nm) under ultrasound irradiation has been demonstrated.
The present method offers advantages such as shorter reaction time, easy work-up, excellent yields, recovery and reusabil-
ity of catalyst. In addition, the methodology has been prosperous in getting the green chemistry purposes such as natural
catalyst, using ultrasound irradiation instead of conventional heating and stirring, and a non-hazardous products in the thus
combining the features of both economic and environmental advantages.
Keywords N-Cyclohexyl-3-aryl-quinoxaline-2-amine · Perlite–SO3H nanoparticles · Multicomponent reaction · Ultrasound
irradiation
Introduction
the basic frame (Fig. 1) [13, 14]. The quinoxaline ring is also
a constituent of many biologically and pharmacologically
active compounds such as anthelmintics, fungicides, insec-
ticides and herbicides [15, 16]. Quinoxaline derivatives have
gained usage in dyes [17], electron luminescent substances
[18], organic semiconductors [19], chemically controllable
switches [20], as building blocks for the synthesis of anion
receptors [21], cavitands [22], dehydroannulenes [23], DNA
unzipping agents [24], and also minister as effective strict
subunits in macrocyclic receiver or in molecular diagnosis
[25, 26].
During the past decade, isocyanide-based multicomponent
reactions (IMCRs) achieved important concern within the
scientific association as an effective, appropriate, time-
saving, and atom-economical procedure to quickly produce
chemical variety. IMCRs are quickly done using readily
accessible starting materials and sustain a diversity range
of functional groups. Alteration and following transforma-
tions prepare achievement to a justly great number of unique
structures that would otherwise need prolix preparations
[1–6]. Therewith, IMCRs have been extensively used in the
pharmaceutical industry [7–9].
The usage of heterogeneous catalysts [27–30] has gained
significant gravity in organic synthesis because of their facil-
ity of operation, elevated reaction rates, greater selectivity,
easy work-up, and recoverability of catalysts. Between the
different heterogeneous catalysts, exclusively, nano-perlite
has advantages of eco friendly, low cost, ease of preparation
and catalyst recycling [31]. Perlite is an amorphous volcanic
glass that has a relatively high water value, typically formed
by the hydration of obsidian. Because of its low density and
relatively low price, many commercial applications for per-
lite have developed. In the construction and manufacturing
fields, it is used in lightweight plasters and mortars, insu-
lation and ceiling tiles. There are few reports about using
perlite as suitable support for catalytic applications [31–35].
Quinoxaline derivatives are a usual incidence in plenty
pharmacological active materials of natural or synthetic
sources [10–12]. Many recognized antibiotics containing
echinomycin, actinomycin, triostin A and leromycin have
* Morteza Rouhani
rouhani.morteza@gmail.com
1
2
Department of Chemistry, Science and Research Branch,
Islamic Azad University, Tehran, Iran
Department of Chemistry, University of Zanjan, P O
Box 45195-313, Zanjan, Iran
Vol.:(0123456789)
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Journal of the Iranian Chemical Society
Ultrasound irradiation is well known to speed up chemi-
cal reactions [36, 37]. This is due to the event of acoustic
cavitation, that is, the formation, development and crash of
micrometrical bubbles, formed by the propagation of a pres-
sure wave through a liquid. The crashes are quasiadiabatic
processes, resulting in the production of high temperatures
and pressures in the nanosecond time size, attended by
sonoluminescence and mechanical effects. These effects can
be applied to speed up chemical reactions, decreasing the
reaction time and optimizing the profit–charge relevance.
Moreover, this energetic flow can help to push forward both
desirable and undesirable chemical reactions [36]. There-
fore, the yields received with ultrasound-assisted reactions
are various than those received under the similar conditions
with classical synthetic methods [37].
(made in Germany) with 20 kHz processing frequency, a
nominal power 250 W and uniform sonic waves.
Preparation of perlite NPs
Perlite NPs were prepared from perlite mineral powder
according to the preparation of silica nanoparticles from
organic laboratory waste of silica gel HF254 method [45]
The morphology and grainsize of the perlite NPs was inves-
tigated by SEM and XRD (Figs. 1, 2, 3).
Preparation of perlite–SO3H NPs
A 250-mL suction flask was equipped with a constant pres-
sure dropping funnel containing chlorosulfonic acid (11.6 g,
0.1 mol) and a gas inlet tube for conducting HCl gas over
an adsorbing solution, i.e., H2O. Then 30.0 g of nanoperlite
was charged in to the flask. Chlorosulfonic acid was added
As part of our continuing interest to develop the new
ultrasound-promoted isocyanide-based multicomponent
reactions [38–40], herein, we wish to report a green, effec-
tive and suitable method for the synthesis of N-cyclohexyl-
3-aryl-quinoxaline-2-amine derivatives 4 using per-
lite–SO3H nanoparticles as catalyst through one-pot
condensation reaction of o-phenylenediamine 1, aromatic
aldehydes 2 and cyclohexyl isocyanide 3 (Scheme 1). We
think that our work is in good agreement with the principles
of green chemistry [41–44] such as inhibition of the forma-
tion of waste materials, having very high atom economy,
eschewing of hazardous products, modeling safer products,
using natural volcanic rock as catalyst, energy economy with
operating reaction under ultrasonic irradiation and elimina-
tion of chemical stages with one-pot reaction.
Experimental
General
All reagents were purchased from Merck (Germany) and
Fluka (Switzerland) and used without further purification.
Infrared spectra were recorded on a Jasco 6300 FTIR spec-
trometer. Melting points were measured on an Electrother-
mal 9100 apparatus and are uncorrected. Sonication was per-
formed in a Bandelin SONOPULS ultrasonic homogenizers
Fig. 1 Echinomycin (top) and triostin A (down) [13, 14]
Scheme 1 Synthesis of
R
C
N
N-cyclohexyl-3-aryl-quinoxa-
CHO
line-2-amine derivatives 4a-i
NH2
NH2
N
Perlite-SO3H NP
EtOH, )))
N
4
N
H
R
1
3
2
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Journal of the Iranian Chemical Society
Fig. 2 SEM of the synthesized perlite nanoparticles
Fig. 3 X-ray diffraction pattern
of the prepared perlite nano-
particles
drop wise over a period of 30 min at room temperature. HCl
gas evolved from the reaction vessel immediately. After the
addition was complete, the mixture was shaken for 30 min.
Perlite–SO3H was obtained as a white solid. The SEM image
of the synthesized perlite–SO3H nanoparticles has been
showed in Fig. 4.
titration of the sample suspended in toluene with n-buty-
lamine, using an indicator. The 0.1 N n-butylamine solu-
tion was provided by weighing 1.0 mL of n-butylamine in a
100-mL volumetric flask and making up the volume using
dried toluene. Then, 0.2 g of dried perlite–SO3H sample
was transferred to a 50-mL Erlenmeyer flask. 9 mL of dry
toluene and 3 mL of indicator solution in toluene were added
to the sample suspension. Then, enough 0.1 N n-butylamine
in toluene was added from a 2-mL burette to the sample so
as to bracket the expected titer by the appropriate number
of millimoles of n-butylamine per gram of perlite–SO3H
sample. The tightly capped sample was then equilibrated
in a rotator at least for 4 h at room temperature. The titra-
tion was then continued using smaller stepwise increases in
n-butylamine content until the end point.
Acid strength measurement
Color test was done by moving 0.1 g of dried, powdered
solid perlite–SO3H NPs to a test tube, adding a 0.1% solution
of methyl red in toluene as an indicator (three drops). From
the color changing to red, it was easy to decide that the solid
perlite–SO3H NPs was acidic [46].
Acid amount determination
The quantity of acid sites on perlite–SO3H NPs can be evalu-
ated by amine titration directly after determination of acid
strength by mentioned method [45]. The method includes
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Journal of the Iranian Chemical Society
Fig. 4 The SEM image of the prepared perlite–SO3H nanoparticles
cyclohexyl isocyanide 3 were first reacted in EtOH (10 mL)
for 40 min under ultrasound irradiation in the presence 0,
10, 20, 50, 100 and 200 mg of perlite–SO3H nanoparticles
separately. The best results were taken using 100 mg of cata-
lyst (yield=94%). Using lower amounts of catalyst resulted
in lower yields, while higher amounts of catalyst did not
affect the reaction times and yields and in the absence of
catalyst, the yield of the product was found to be very low
[33] (Table 1).
General procedure for the one‑pot synthesis
of N‑cyclohexyl‑3‑phenyl‑quinoxaline‑2‑amines
To a mixture of o-phenylenediamine 1 (1 mmol), benzalde-
hyde 2a (1 mmol), and cyclohexyl isocyanide 3 (1 mmol) in
EtOH (10 mL), a catalytic amount of perlite–SO3H (100 mg)
was added and the mixture was irradiated under an ultra-
sonic processor at 150 W. The improvement of the reaction
was monitored by TLC (ethyl acetate–hexane 1:3). After
completion of the reaction, the resulting solid (catalyst) was
separated by simple filtration and EtOH was removed and
the reaction mixture was diluted with water (15 mL), and
CH2Cl2 (15 mL) was added. The organic layer was separated
and dried over MgSO4. The solvent was evaporated under
reduced pressure, and the product was obtained without any
further purification.
Table 1 Effect of amounts of catalyst pelite–SO3H NP with or with-
out sonication for synthesis of N-cyclohexyl-3-phenyl-quinoxaline-
2-amine (4a) [33]
Entry Pelite–
With sonicationa
Without sonicationb
Yieldc (%) Time (min)
SO3H NPs
Results and discussion
Yieldc (%) Time
(mg)
(min)
The amount of acid in the perlite–SO3H NPs samples was
investigated. It can be seen that the amount of acidity was
observed in the case of perlite–SO3H NPs as 2.46 mmole/g.
To get appropriate conditions for the synthesis of
N-cyclohexyl-3-aryl-quinoxaline-2-amine (4a–i), differ-
ent reaction conditions have been studied in the reaction
of o-phenylenediamine 1, benzaldehyde 2a and cyclohexyl
isocyanide 3 as a model reaction.
1
2
3
4
5
6
0
10
20
50
100
200
Nil
12
34
66
94
94
75
60
60
60
40
40
Nil
8
20
20
52
52
160
160
160
160
120
120
aReaction condition: reaction of o-phenylenediamine 1, benzaldehyde
2a and cyclohexyl isocyanide 3 in EtOH in the presence of various
amount of perlite–SO3H under ultrasound irradiation
Effects of the catalyst under ultrasound irradiation
bReaction condition: reaction of o-phenylenediamine 1, benzaldehyde
2a and cyclohexyl isocyanide 3 in EtOH in the presence of various
amount of perlite–SO3H under reflux condition
In a primary study, for examination of the amount of catalyst
cYields of isolated products
in this reaction, o-phenylenediamine 1, benzaldehyde 2a and
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Journal of the Iranian Chemical Society
Table 2 The model reaction in different conditions under ultrasound
irradiation for synthesis of N-cyclohexyl-3-phenyl-quinoxaline-
2-amine (4a)
Table 5 The recycling of
perlite–SO3H NPs in synthesis
of N-cyclohexyl-3-phenyl-
quinoxaline-2-amine 4a
Entry Time (min) Yield (%)a
1
2
3
4
5
40
40
80
80
120
94
94
88
88
82
Entry
Solvent
Time (min)
Yielda (%)
1
2
3
4
5
6
7
Water
60
60
60
60
60
40
50
32
73
84
45
51
94
94
Methanol
Acetonitrile
THF
Dioxane
EtOH
aIsolated yields
Effects of the solvents under ultrasound irradiation
EtOH
Reaction condition: reaction of o-phenylenediamine 1, benzaldehyde
2a and cyclohexyl isocyanide 3 in the presence of perlite–SO3H in
various solvents under ultrasound irradiation
Here, we have varied the solvents condition such as water,
methanol, acetonitrile, THF, dioxane and ethanol, the
observation showed that the reaction using EtOH as solvent
gave the best result, which gave the products not only in
good yield but also with higher reaction rates (94% yield in
40 min) (Table 2, entry 6). Acetonitrile afforded moderate
yields of desired products but took comparatively longer
reaction time (Table 2, entry 3).
aIsolated yields
Table 3 Perlite–SO3H catalyzed synthesis of N-cyclohexyl-3-phenyl-
quinoxaline-2-amine (4a) under various ultrasound irradiation powers
in EtOH [39]
Entry
Power (W)
Time (min)
Yielda (%)
Effects of the ultrasound power
1
2
3
4
50
100
150
200
60
60
40
40
52
75
94
94
By enhancing the irradiation power from 50 to 150 W, the
reaction time of 4a reduced from 60 to 40 min and the yield
increased from 52 to 94%. The reaction time and yield of 4a
did not shift from 150 to 200 W, thus, 150W of ultrasonic
irradiation was enough to push the reaction forward. The
best yield for 4a was gained by ultrasonic irradiation for
40 min 150 W (Tables 3, 4) [39, 40].
Reaction condition: Reaction of o-phenylenediamine 1, benzaldehyde
2a and cyclohexyl isocyanide 3 in the presence of perlite–SO3H in
EtOH under different ultrasound powers
aIsolated yields
Table 4 Perlite–SO3H catalyzed
synthesis of N-cyclohexyl-
3-aryl-quinoxaline-2-amine
derivatives 4a-i under
ultrasound irradiation in EtOH
[40]
Entry
Ar
Producta
Yieldb (%)
Time (min)
Mp (°C)
Found
Reported
1
2
3
4
5
6
7
8
9
C6H5
3-
NO2C6H5
4-ClC6H5
4-
4a
4b
4c
4d
4e
4f
4 g
4 h
4i
94
93
93
94
92
93
92
94
91
40
38
38
42
37
37
40
37
40
186–187
193–195
190–192
178–179
18721
19521
19221
17921
20921
MeOC6H5
17621
20121
4-
185-18722
192-19422
NO2C6H5
4-OHC6H5
4-MeC6H5
4-FC6H5
208–209
174–176
200–201
186–187
192–194
3-MeC6H5
Reaction condition: reaction of o-phenylenediamine 1, aromatic aldehydes 2 and cyclohexyl isocyanide 3
in the presence of perlite–SO3H in EtOH under ultrasound irradiation
aProducts are characterized by melting point, IR and comparison with the literature
bIsolated yields
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Journal of the Iranian Chemical Society
Scheme 2 Proposed mecha-
nism for the formation of
R
N-cyclohexyl-3-aryl-quinoxa-
line-2-amine derivatives 4a-i
CHO
NH
NH2
NH2
)))
Perlite-SO3H NP
EtOH, )))
C
NH2
R
N
A
1
2
R
3
R
H
N
H
N
)))
)))
NH2
N
H
N
N
B
C
R
R
H
N
N
N
4
)))
-2H
HN
N
HN
catalytic
dehydrogenation36
Reusability of catalyst
Conclusion
Next, we investigated the reusability and recycling of per-
lite–SO3H nanoparticles. At first, we put o-phenylenedi-
amine 1 (1 mmol), benzaldehyde 2a (1 mmol), cyclohexyl
isocyanide 3 (1 mmol) and perlite–SO3H NPs in EtOH
(10 mL) as solvent at 150 W under sonication. When the
reaction was completed (monitored by TLC), the result-
ing solid (catalyst) was separated by simple filtration and
recovered perlite–SO3H was reused in subsequent reactions
without significant decrease in activity even after five runs
(Table 5).
In summary, we have extended a new, efficient and environ-
ment friendly one-pot three-component method for the syn-
thesis of N-cyclohexyl-3-aryl-quinoxaline-2-amine deriva-
tives under ultrasound irradiation in excellent isolated yields
using EtOH as an almost non-hazardous, inexpensive and
readily available solvent. The various substituents (electron-
donating and electron-withdrawing) on each component of
the coupling partner were well tolerated. The combination
of the relatively fast reaction times, simple work-up meth-
ods and the aspects stated above mean that the methodology
can be operated in a combi-chem mode to produce libraries
organizing a various array of N-cyclohexyl-3-aryl-quinoxa-
line-2-amine derivatives.
The feasible mechanism for the formation of product 4
is shown in Scheme 2. Product 4 is formed by the primary
formation of minimum intermediate A from diamine 1 and
aldehyde 2. Intermediate B was made by the nucleophilic
attack of isocyanide 3 to the iminium intermediate A and
next by an intramolecular nucleophilic attack of NH2 group
to the nitrile moiety to yield intermediate C. Imine–enamine
tautomerization of intermediate C and then catalytic dehy-
drogenation leads to the formation*** of product 4.
Acknowledgements The authors thank Science and Research Branch,
Islamic Azad University for the support and guidance.
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Journal of the Iranian Chemical Society
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