Pectin; hetero polysaccharide as a green and natural catalyst for the synthesis of dihydro-2-oxopyrroles and 3,4,5-trisubstituted furan-2(5H)-ones

Article abstract of DOI:10.4067/S0717-97072018000404168

Use of green and biodegradable catalyst in organic synthesis is undeniable. Easy access, inexpensive, natural and green catalysts are valuable. In this study, a green procedure by using pectin as a green and natural catalyst for the one-pot synthesis of dihydro-2-oxopyrroles and 3,4,5-trisubstituted furan-2(5H)-ones at ambient temperature in aqueous media has been developed. This methodology has some advantages such as: use of a hetero polysaccharide as a easy access and biodegradable catalyst, clean work-up and no need to column chromatography.

Full text of DOI:10.4067/S0717-97072018000404168

J. Chil. Chem. Soc., 63, Nº 4 (2018)
PECTIN; HETERO POLYSACCHARIDE AS A GREEN AND NATURAL CATALYST FOR THE SYNTHESIS OF
DIHYDRO-2-OXOPYRROLES AND 3,4,5-TRISUBSTITUTED FURAN-2(5H)-ONES
MEHRNOOSH KANGANI, NOURALLAH HAZERI*, MALEK-TAHER MAGHSOODLOU
Department of Chemistry, Faculty of Sciences, University of Sistan and Baluchestan, P.O. Box 98135-674,Zahedan, Iran
ABSTRACT
Use of green and biodegradable catalyst in organic synthesis is undeniable. Easy access, inexpensive, natural and green catalysts are valuable. In this study,
a green procedure by using pectin as a green and natural catalyst for the one-pot synthesis of dihydro-2-oxopyrroles and 3,4,5-trisubstituted furan-2(5H)-ones at
ambient temperature in aqueous media has been developed. This methodology has some advantages such as: use of a hetero polysaccharide as a easy access and
biodegradable catalyst, clean work-up and no need to column chromatography.
Keywords: Pectin; dihydro-2-oxopyrroles; 3,4,5-trisubstituted furan-2(5H)-ones
Recently, the most convenient methods have been reported for preparation of
the dihdropyrrol-2-ones by means of domino reaction between amines, dialkyl
acetylenedicarboxylates and aldehydes [25,26] . With widespread applications
and bioactivity, development of efficient approach to dihdropyrrol-2-ones in
terms of mild reaction conditions, operational simplicity, and readily available
material is still in demand.
Sweeney et al. reported the first preparation of 3,4-bistributylstannyl
2(5H)-furanones by reacting TBS as well as THP protected butynoate with
hexabutylditin in the presence of PdCl2(PPh3) leading to substituted acrylate
intermediate, which upon treating under a 2variety of conditions yielded
desired furanone synthon [27-29] . More recently Mauro et al. described the
construction of furanone system via ring-closing metathesis catalyzed by
the first generation Grubbs’ catalyst [30] . However, some of these catalysts
suffer from the drawback of green chemistry such as prolonged reaction times,
low yields, toxicity and recovery and reusability of the catalyst. Therefore,
introducing clean processes and utilizing eco-friendly and green catalysts
which can be simply worked-up at the end of reactions have been under
permanent attention.
INTRODUCTION
Pectin is one of the major plant cell wall components and probably the
most complex macromolecule in nature, as it can be composed out of as many
as 17 different monosaccharides containing more than 20 different linkages
[1–3]. Pectin is used in foods mainly as gelling, stabilizing, or thickening agent
in products such as jam, yoghurt drinks, fruity milk drinks, and ice cream [4].
Most of the pectin used by food industry originates from citrus or apple peel
from which it is extracted at low pH and high temperature and is primarily a
homogalacturonan [5]. In products that naturally contain pectin, e.g., fruit and
vegetables, important quality changes during storage and processing are related
to changes in pectin structure. Native or added pectic enzymes can play an
important role in these changes [6] (Figure 1).
Dihydropyrroles are important azaheterocycles with various biological
activities [7]. For example, dihydropyrrole derivatives have been used as the
inhibitors of bacterial peptide deformylase [8] , human mitotic kinesin Eg5 [9] ,
cardiac CAMP phosphodiesterase [10] , human immunodeficiency virus (HIV)
integrase [11] , and vascular endothelial growth factor receptors (VEGFR) [12]
. They are also useful intermediates in the synthesis of natural products6 and
chemicals [13] . Thus, the development of efficient synthetic methodologies
for novel dihydropyrroles has attracted tremendous interests in synthetic
chemistry. Moreover, the dihydropyrrol-2-one unit is the core structure in a
number of natural products [14-17] . As a result, considerable efforts have
been made for the synthesis of this important class of compounds [18-24] .
Therefore, In continuation to our greener method development program
[31-37] ,we have found hetero polysaccharide pectin as a green catalyst which
is cheap and easily available. We investigated its potential for catalyzing the
synthesis of dihydro-2-oxopyrroles and 3,4,5-trisubstituted furan-2(5H)-
ones (Scheme 1) and the results are presented in this paper. The process is
remarkably simple, high yielding, highly efficient, time and energy saving.
Figure 1.The structure of pectin.
e-mail: nhazeri@chem.usb.ac.ir
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J. Chil. Chem. Soc., 63, Nº 4 (2018)
Scheme 1. Synthesis of dihydro-2-oxopyrroles and 3,4,5-trisubstituted furan-2(5H)-ones in the presence of pectin as green and natural
catalyst at ambient temperature in aqueous media.
Table2. Influence of different solvents for the synthesis of dihydro-2-
oxopyrroles in the presence of pectin (0.05 g) at ambient temperature.
RESULTS AND DISCUSSION
The reaction of aniline, dimethylacetylendicarboxylate and formaldehyde
was chosen as a model system for optimization the reaction conditions. The
reaction was performed with different amount of solvent and catalyst. The
results are summarized in table 1 and table2. Since we wanted to present a
green and environmentally benign protocol for this experiment, we did not test
any other organic solvents under these conditions.
Entry
Solvent
H2O
Yield(%)
1
2
3
4
5
6
59
65
68
79
75
75
H2O:EtOH(1:1)
H2O:EtOH(1:2)
H2O:EtOH(1:3)
H2O:EtOH(1:4)
EtOH
Table 1. Effect of amount of catalyst for the synthesis of dihydro-2-
oxopyrroles.
Entry
Catalyst loading (g)
Time (min)
Yield (%)
1
2
3
4
5
0.02
0.03
0.04
0.05
0.06
120
100
90
42
52
63
79
79
Next the reaction conditions were optimized for the synthesis of
3,4,5-trisubstituted furan-2(5H)-ones, the best results was found at ambient
temperature with (0.05 g ) of pectin in H2O:EtOH (1:3).
The scope and efficiency of these procedures were explored for the
60
synthesis of
a wide variety of substituted dihydro-2-oxopyrroles and
3,4,5-trisubstituted furan-2(5H)-ones. A series of aromatic aldehydes and
amines were investigated (Table 3). Interestingly, a variety of aryl aldehydes
and amines including electron withdrawing or releasing substituents (ortho-,
meta-, and para-substituted) participated well in this reaction and gave the
products in good to excellent yield.
60
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J. Chil. Chem. Soc., 63, Nº 4 (2018)
Table 3. Synthesis of dihydro-2-oxopyrroles and 3,4,5-trisubstituted furan-2(5H)-ones.
Product
5a
5b
5c
5d
5e
5f
Ar1
Ar2
R
Time (min) yield (%)
m.p (°C)
153–154
135–137
170–172
125–128
151–153
160–163
161–163
167–169
136–138
81 127
Lit.mp (°C) [Ref]
155–156 [26]
138–140 [25]
177–178 [26]
131–132 [25]
152–154 [32]
163–165 [32]
168–170 [32]
169–171 [32]
140–141 [25]
129 130 [25]
166–168 [32]
120–121 [26]
144–146 [32]
159-162 [30]
284-287 [30]
181-183 [30]
149-152 [30]
152–154 [37]
293-295 [32]
165–166 [32]
203-205 [32]
239-242 [32]
130-131[32]
164–166 [32]
120–121 [32]
188-191 [32]
184-185 [32]
174 [32]
Ph
Ph
Me
Et
60
60
50
60
120
60
60
90
60
60
60
60
60
120
70
60
60
40
50
60
90
60
80
60
60
60
60
60
79
75
85
75
80
85
85
80
85
80
70
70
75
75
80
85
85
80
85
85
80
85
80
70
80
85
80
80
Ph
Ph
4-Me-C6H4
4-Me-C6H4
4-Me-C6H4
4-Me-C6H4
Me
Et
4-OMe-C6H4 4-OMe-C6H4
Et
4-F-C6H4
4-Cl-C6H4
4-Br-C6H4
PhCH2
4-F-C6H4
4-Cl-C6H4
4-Br-C6H4
Ph
Me
Et
5g
5h
5i
Et
Me
Et
5j
PhCH2
Ph
5k
5l
PhCH2
4-F-C6H4
4-Br-C6H4
4-Me-C6H4
Ph
Me
Me
Me
Me
Me
Me
Me
Et
166–168
119–121
144–146
157-1158
281-283
185-186
150–152
150–152
290-293
167–170
199-202
235-238
129-130
166–168
119–121
185-186
180-182
174-176
PhCH2
5m
9a
9b
9c
9d
9e
9f
PhCH2
Ph
Ph
4-Me–C6H4
Ph
4-Me-C6H4
4-Cl-C6H4
4-CN-C6H4
Ph
Ph
Ph
4-F-C6H4
4-Cl-C6H4
3-NO2-C6H4
Ph
Me
Me
Me
Me
Me
Et
9g
9h
9i
Ph
Ph
4-OMe–C6H4
4-NO2–C6H4
Ph
9j
Ph
9k
9l
Ph
Ph
4-Me–C6H4
Ph
Et
9m
9n
9o
4-Me–C6H4
4-Cl–C6H4
4-OMe–C6H4
Et
Ph
Et
Ph
Et
A proposed mechanism for the formation of 9a is shown in scheme 2. Pectin has many free carboxyl group that can active carbonyl group and accelerate the
reaction procedure.
Scheme 2. Proposed mechanism for the synthesis of dihydro-2-oxopyrroles in the presence
of pectin as a green catalyst.
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J. Chil. Chem. Soc., 63, Nº 4 (2018)
We also investigated the recycling of the catalyst at ambient temperature
in aqueous media for the synthesis of3,4,5-trisubstituted furan-2(5H)-ones,
using a model reaction of 4-methylbenzaldehyde, aniline and dimethyl
acetylendicarboxylate. After completion of the reaction, 5 mL of water was
added to the mixture. The pectin was dissolved in water and filtered for
separation of the crude product. The separated product was washed with EtOH
(3×2 mL) to give the pure products. In order to recover the catalyst, since pectin
is soluble in water, the filtrate was extracted with diethyl ether. The aqueous
layer (including pectin) was separated, and its solvent was evaporated under
reduced pressure and pectin was recovered and reused. The catalytic system
worked well up to five catalytic runs. The recovered catalyst was reused five
times without any loss of its activities (Figure 2).
EXPERIMENTAL
Materials and Methods
IR spectra were obtained on a JASCO FT/IR-460 plusspectrometer.
Melting points were taken on an Electrothermal 9100 apparatus. Chemicals
were purchased from Merck (Darmastadt,Ge rmany), Acros (Geel, Belgium)
and Fluka (Buchs, Switzerland), and used without further purification.
General procedure for the synthesis of dihydro-2-oxopyrroles
A mixture of amine 1 (1 mmol) and dialkyl acetylenedicarboxylate 2 (1
mmol) in H2O:EtOH (1:3) was stirred for 25 min. Next, amine 3 (1 mmol),
formaldehyde 4 (37% solution, 1.5 mmol) and pectin (0.05 g) were added in
successively. The reaction mixture was allowed to stir at ambient temperature
for appropriate time. After completion of the reaction (monitored by TLC),
the precipitate was filtered off and washed with ethanol (3× 2 mL) to give the
pure product 5.
General procedure for the synthesis of 3,4,5-trisubstituted furan-
2(5H)-ones
A mixture of amine 6 (1 mmol) and dialkyl acetylenedicarboxylate 7 (1
mmol) , aromatic aldehyde 8 (1mmol) and pectin (0.05 g) in H O:EtOH (1:3)
was stirred at ambient temperature for appropriate time. After2completion of
the reaction (monitored by TLC), the precipitate was filtered off and washed
with ethanol (3×2 mL) to give the pure product 9.
Characterization data of some compounds
Methyl
2,5-dihydro-5-oxo-1-phenyl-4-(phenylamino)-1H-pyrrole-3-
carboxylate (5a). White solid, IR (KBr) (δ max, cm-1): 3310 (NH), 1705, 1684,
1645;1H NMR (400 MHz, CDCl3): δ(ppm): 3.76 (3H, s, OCH3), 4.57 (2H, s,
CH ), 7.16-7.23 (4H, m, ArH),7.34 (2H, t, J = 8.0 Hz, ArH), 7.42 (2H, t, J = 8.0
Hz,2ArH), 7.81(2H, d, J = 8.0 Hz, ArH), 8.05 (1H, br s, NH).
Ethyl
4-(p-tolylamino)-2,5-dihydro-5-oxo-1-p-tolyl-1H-pyrrole-3-
carboxylate (5d). Yellow solid, IR (KBr) (δ max, cm-1): 3310 (NH), 1707, 1682,
1649; 1H NMR (400 MHz, CDCl3): δ(ppm): 1.25 (3H,t, J = 7.2 Hz, OCH2CH3),
2.36 (3H, s, CH3), 2.37 (3H, s, CH3),4.23 (2H, t, J = 7.2Hz, OCH CH3), 4.52
(2H, s, CH2), 7.06 (2H, d,J = 8.4 Hz, ArH), 7.14 (2H, d, J = 8.0 Hz,2ArH), 7.21
(2H, d, J =8.4 Hz, ArH), 7.69 (2H, d, J = 8.8 Hz, ArH), 8.01 (1H, br s, NH);13C
NMR (100 MHz, CDCl3): δ(ppm): 14.2, 20.9, 21.0, 48.3, 60.2,102.4, 119.1,
122.9, 128.9, 129.6, 134.2, 134.6, 136.2, 136.3,143.1, 163.7, 164.7.
Figure 2. The investigation of the recycling of pectin.
Methyl 2,5-dihydro-5-oxo-2-phenyl-4-(phenylamino)furan-3-carboxylate
(9a): White solid; IR (KBr) (δ max, cm-1): 3260, 3208, 1702, 1661; 1HNMR(400
MHz, CDCl ): δ (ppm): 3.77 (s, 3 H, OCH3), 5.76 (s, 1H, benzylic), 7.13
(t, 1H, J = 73.3 Hz),7.24–7.31 (m, 7H), 7.52 (d, 2H, J = 8 Hz), 8.90 (br, NH,
1H); 13C NMR(100 MHz, CDCl ): δ(ppm): 165.3 and 162.7 (ester CO), 156.3,
136.1, 134.9,129.0, 128.7, 1283.6, 127.4, 125.9, 122.3, 112.8 (aromatic C),
61.6(methoxy C), 52.1 (benzylic C).
In order to assess the efficiency and generality of this methodology, the
obtained result from this methodology has been compared with those of the
previously reported methods (Table 4). It was found that the present method
is convincingly superior to the reported methods with respect to reaction time
and condition and yield of the product. According to the green chemistry law,
If possible, synthetic methods should be conducted at ambient temperature and
pressure to reduce the energy consume [38]. This methodology has been done
at ambient condition for economic and environmental impacts.
Methyl 4-(p-tolylamino)-2,5-dihydro-5-oxo-2-phenylfuran-3-carboxylate
1
(9b): White solid; IR (KBr) (δ max, cm-1): 3228, 2950, 1706, 1677, 1513; H
NMR (400 MHz,CDCl3): δ(ppm): 2.27 (s, 3H, CH ), 3.76 (s, 3H, OCH3), 5.72
(s, 1H, benzylic),7.09 (d, 2H, J = 8 Hz), 7.22–7.2370 (m, 5H, aromatic), 7.34
(d, 2H,J = 8.4 Hz), 8.86 (br, 1H, NH); 13C NMR (100 MHz, CDCl3): δ(ppm):
165.3and 162.8 (CO of ester), 156.4, 135.8, 135.0, 133.5, 129.6, 128.6,128.5,
127.5, 122.4, 112.6 (C of aromatic), 61.3 (C of methoxy), 52.0 (benzylic C),
20.95 (C of methyl).
Table 4. Comparison of the efficiency of pectin with other reported
catalysts in literature.
Isolated
yield
(%)
Catalyst/
Condition
Entry Product
Time
References
Ethyl
2-(4-cyanophenyl)-2,5-dihydro-5-oxo-4-(phenylamino)-furan-3-
AcOH/EtOH,
70 оC
1
2
3
5a
5a
5a
30 min
60 min
5 h
89
83
83
[39]
[40]
[41]
carboxylate (9e): White solid; IR (KBr) (δ max, cm-1): 3293 (NH), 2977, 2225
(CN), 1731, 1684,1666, 1500; 1H NMR (400 MHz, CDCl3): δ(ppm): 1.23 (t,
3H, J = 7.2 Hz,CH3), 4.24 (q, 2H, J = 7.2 Hz, CH2), 5.82 (s, 1H, benzylic), 7.17
(t, 1H,J = 7.2 Hz), 7.32–7.47 (m, 6H, aromatic), 7.59 (d, 2H, J = 8 Hz), 9.03(br,
1H, NH); 13C NMR (100 MHz, CDCl3): δ(ppm): 164.6, 162.5 (CO ofester),
156.89, 140.8, 135.7, 132.5, 129.2, 128.3, 126.3, 122.1, 118.1,112.6 (aromatic
C), 112.2 (C of CN), 61.6 (methoxy), 60.8 (benzylic),14.02 (CH3 of ethoxy).
I2,MeOH,r.t
Al(H2PO4) ,
MeOH,r.t3
Pectin,
H2O:EtOH, r.t
Present
work
4
5
6
7
8
5a
9a
9a
9a
9a
60 min
12 h
79
78
86
83
75
CONCLUSION
Cyclodextrin /
[42]
[43]
[42]
H2O, 60-70 оC - β
In summary, an eco-friendly and straightforward one-pot condensation
for the synthesis of dihydro-2-oxopyrroles and 3,4,5-trisubstituted furan-
2(5H)-ones in the presence of pectin as a highly effective, green, natural
and biodegradable catalyst was reported. Pectin is inexpensive, clean, safe,
nontoxic, and easy access. Moreover, this method has several other advantages
such as, high yields, operational simplicity, reusable catalyst, clean and neutral
reaction conditions, which makes it a useful and attractive process for the
synthesis of a wide variety of biologically active compounds.
SnCl2, EtOH,
7h
reflux
ZnO, EtOH: H2O,
90 оC
150 min
120 min
Pectin,
H2O:EtOH, r.t
Present
work
4171

J. Chil. Chem. Soc., 63, Nº 4 (2018)
37. R.Doostmohammadi, M.T.Maghsoodlou, N.Hazeri, S.M. Habibi-
Khorassani, Chin.Chem.lett, 24, 901 (2013)
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(2009)
We gratefully acknowledge financial support from the ResearchCouncil of
the University of Sistan and Baluchestan.
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