Acetic acid as an efficient catalyst for the one-pot preparation of 3,4,5-substituted furan-2(5H)-ones

Article abstract of DOI:10.1007/s11164-012-0922-1

The three-component condensation reaction of aldehydes, amines,and dialkyl acetylenedicarboxylates was conducted, leading to the production of 3,4,5-substituted furan-2(5H)-ones. This reaction is performed in the presence of acetic acid as a cheap and readily available catalyst at room temperature. Graphical Abstract: [Figure not available: see fulltext.]

Full text of DOI:10.1007/s11164-012-0922-1

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Letters in Organic Chemistry, 2013, 10, 199-203
199
Application of Silica Gel-supported Polyphosphoric Acid (PPA/SiO2) as a
Reusable Solid Acid Catalyst for One-Pot Multi-Component Synthesis of
3,4,5-substituted furan-2(5H)-ones
Razieh Doostmohammadi and Nourallah Hazeri*
Department of Chemistry, Faculty of Science, University of Sistan & Baluchestan, P. O. Box 98135-674 Zahedan, Iran
Received December 18, 2012: Revised February 18, 2013: Accepted February 25, 2013
Abstract: 3,4,5-substituted furan-2(5H)-ones were One-Pot Multi-Component synthesized by the reaction of aldehydes,
amines and dialkyl acetylenedicarboxylates using silica gel-supported polyphosphoric acid (PPA/SiO2) at room tempera-
ture. This reaction provides a convenient and efficient synthetic method of furan-2(5H)-one derivatives, and also reusabil-
ity of catalyst.
Keywords: PPA/SiO2, 3,4,5-substituted furan-2(5H)-ones, aldehydes, amines, dialkyl acetylenedicarboxylates.
1. INTRODUCTION
Recently, PPA/SiO2 has been used as an efficient hetero-
geneous catalyst for many organic transformations.
PPA/SiO2 has some advantages including its low cost, ease
of preparation, and ease of handling. In addition, the catalyst
can be easily separated from the reaction mixture by simple
filtration and is reusable. Due to our interest in the synthesis
of of furan [27-33] and in continuation of our previous works
on the synthesis of ꢀ-amino phosphonates using PPA/SiO2
[34] herein we wish to report a novel and convenient method
for the synthesis of 3,4,5-substituted furan-2(5H)-ones de-
rivatives using PPA/SiO2 as a reusable catalyst.
Highly substituted furans play an important role in or-
ganic chemistry, not only as key structural units in many
natural products, common subunits in pharmaceuticals [1-7]
and flavors [8] but also as useful building blocks in synthetic
chemistry [9-13]. They have also found utility as synthetic
intermediates or synthons for numerous functional groups,
inter alia, carboxylic acids, ꢀ-keto-esters, and aromatics [14].
For this reason, the efficient synthesis of multiple substituted
furans continues to attract the interest of synthesis chemists
[15-16]. Accordingly, many strategies have been developed
for the preparation of furans [17-20]. The above-mentioned
methodologies have certain limitations like multistep strate-
gies, use of costly metal catalysts and highly volatile sol-
vents.
RESULTS AND DISCUSSION
We have introduced a one-pot three-component conden-
sation reaction (MCR) that is one of the most useful methods
for the synthesis of organic compounds in an optimistic time,
room temperature, PPA/SiO2 catalyst and involving only a
single step. Moreover, as previously mentioned, reaction
most often leads to product that can be easily separated and
purified by simple filtering and washing out with a regular
solvent. Substrates benzaldehyde, aniline, with dimethyl
acetylenedicarboxylate were taken as model compounds to
be investigated for the optimization of reaction conditions.
The reaction of benzaldehyde, aniline,with dimethyl acetyle-
nedicarboxylate was initially carried out in ethanol using
different catalysts (Table 1). As can be seen, PPA/SiO2 was
found to be most effective in catalyzing the reaction under
room temperature.
Recently, a methodology has been developed for the syn-
thesis of furan-2(5H)ones via a multicompunent reaction of
aromatic amines, aldehydes and dialkyl acetylenedicarboxy-
late. Multi-component reactions (MCR) make possible the
speedy synthesis of molecular libraries that have a high de-
gree of structural diversity. Combinations of different start-
ing materials can produce a variety of products with facility,
a process that is of great value in the search for new drugs
and chemical compounds [21].
Narayana et al. described the synthesis of 2(5H)-furanone
by b-cyclodextrin [22]. Ramesh and Nagarajan reported the
preparation of 2(5H)-furanone via a three-component reac-
tion of a series of aldehydes (aromatic, heterocyclic), dialky-
lacetylenedicarboxylates and 9-alkyl-9H-carbazol-3-amines
in the presence KOH [23]. Recently, we reported an acetic
acid catalyzed synthesis of 2(5H)-furanone via a three-
component reaction of a series of aldehydes (aromatic, het-
erocyclic), dialkylacetylenedicarboxylates and amines [24].
To optimize the catalyst loading, the above model reac-
tion was carried out under different amounts of PPA/SiO2
(0.01, 0.02, 0.03, 0.05, 0.07, 0.1, 0.15 and 0.2 g). It was ob-
served that 0.15 g loading of PPA/SiO2 provided the maxi-
mum yield at the lowest time. Higher percentage loading of
the catalyst did not affect the reaction time and amount of
yield. The data in Table 2 outline the optimization amount of
PPA/SiO2 for for the synthesis of furan-2(5H)-ones .under
room tempreture conditions.
*Address correspondence to this author at the Department of Chemistry,
Faculty of Science, University of Sistan & Baluchestan, P. O. Box 98135-
674 Zahedan, Iran; Tel/Fax: +98-541-2450995;
E-mails: n_hazeri@yahoo.com, nhazeri@chem.usb.ac.ir
1875-6255/13 $58.00+.00
© 2013 Bentham Science Publishers

200 Letters in Organic Chemistry, 2013, Vol. 10, No. 3
Doostmohammadi and Hazeri
H
O
Ar2
CO2R
C
C
N
O
H
N
RO
Ar1
PPA/SiO2
r.t
+
+
Ar1
H
Ar2
H
O
O
CO2R
Scheme 1. Synthesis of furan-2(5H)-one derivatives.
Table 1. Optimization of Catalyst for the Synthesis of furan-2(5H)-ones at Room Temperature.
Entry
Catalyst
Time (h)
Yield(%)a
1
2
3
4
5
6
TiO2
Zn(SO4)2.7H2O
Zr(NO3)4
15
15
12
12
12
1
25
25
30
50
20
90
ZrCl4
HClO4-SiO2
PPA/SiO2
a Isolated yield.
Table 2. Optimization Amount of PPA/SiO2 for the Synthesis of furan-2(5H)-ones. Under Room Tempreture Conditions.
Entry
PPA/SiO2 (g)
Time (h)
Yield(%)a
1
2
3
4
5
6
7
8
0.01
0.02
0.03
0. 05
0.07
0.1
10
9
85
85
85
86
88
88
90
90
5
3.45
3.15
2
0.15
0.2
1
1
a Isolated yield.
mass spectrometry, and elemental analysis. The mass spec-
trum of Methyl 2,5-dihydro-5-oxo-4-(phenylamino)-2-p-
tolylfuran-3-carboxylate (Compound 4b) displayed the mo-
lecular ion peak at m/z = 323, which is consistent with the
Under the optimized reaction conditions, the generality
of the reaction was investigated by using a variety of alde-
hydes, anilines and dialkyl acetylenedicarboxylate to pro-
duce furan-2(5H)-one derivatives. The results are summa-
rized in Table 3. These results indicate the effectiveness of
electron-withdrawing and electron-donating groups on the
time and yield of the reaction. Benzaldehydes with electron-
withdrawing groups react with aniline better than electron-
donating groups for generation of furan-2(5H)-ones in good
to high yields. In our research work, aliphatic aldehyde and
amine such as propanal and 1-buthyl amin did not practically
did not tolerate the reaction.
1
proposed structure. The H NMR spectrum of this product,
exhibited a singlet at ꢀ = 2.29 ppm for methyl protons, a sin-
glet at ꢀ = 3.77 ppm for methyl protons of the carboxylate
group and one sharp singlet arising from benzylic proton at ꢀ
= 5.73 ppm. The aromatic protons of product were observed
at ꢀ = 7.07 -7.49 ppm. A broad singlet for the NH group at ꢀ
= 8.9 ppm indicated intramolecular hydrogen bond formation
with the vicinal carbonyl group. The 13C NMR spectrum of
this product was showed 15 distinct resonances in agreement
with the proposed structure. The IR spectrum indicated one
sharp peak at 3220 cm-1 for NH within product.
The speculative proposed mechanism for the formation 4
is shown in Scheme 2.
The structures of new compounds in Table 3 were de-
The reusability of the catalyst is an important factor from
economical and environmental point of views and has at-
1
duced on the basis of IR, H, and 13C NMR spectroscopy,

Application of Silica Gel-supported Polyphosphoric Acid
Letters in Organic Chemistry, 2013, Vol. 10, No. 3 201
Table 3. Synthesis of furan-2(5H)-one Derivatives.
Entry
Ar1
Ar2
R
Products
Time (h)
Yield(%)a
Ref.b
1
2
Ph
4-Me-C6H4
3-NO2-C6H4
4-CN-C6H4
Ph
Ph
CH3
CH3
4a
4b
4c
4d
4e
4f
1
2
90
80
87
92
91
85
80
81
62
60
67
75
80
61
90
ꢀ
Ph
ꢀ
3
Ph
CH3
1.5
1
ꢀ
4
Ph
CH3CH2
CH3CH2
CH3CH2
CH3CH2
CH3CH2
CH3CH2
CH3CH2
CH3
ꢀ
5
Ph
1
[22]
[22]
[22]
[22]
[22]
[22]
[24]
[24]
[24]
[24]
[24]
6
Ph
4-Me-C6H4
2
7
4-Me-C6H4
4-Cl-C6H4
4-OMe-C6H4
1- naphtyl
Ph
Ph
4g
4h
4i
2
8
Ph
Ph
3.5
8
9
10
11
12
13
14
15
Ph
4j
8
4-F-C6H4
4-Cl-C6H4
3-NO2-C6H4
Ph
4k
4l
7
Ph
CH3
6
Ph
CH3
4m
4n
4o
7
4-OMe-C6H4
CH3
9
4-NO2-C6H4
Ph
CH3
4
22,24Yields refer to the pure isolated products
aThe new compounds synthesized in this work.
derivatives
H
O
H
O
O
H
N
Ar2
OR
Ar2
N
CO2R
C
C
N
CO2R
CO2R
H
N
RO
H
Ar1
RO
-OR
Ar1
H
Ar2
+
Ar2
H
H
Ar1
O
O
H
O
O
CO2R
Scheme 2. The speculative proposed mechanism for the formation of furan-2(5H)-one derivatives.
Table 4. Investigation of Reusability of the Catalyst in the Reaction between Benzaldehyde, Aniline, and Dimethyl Acetylenedicar-
boxylate in the Presence of PPA-SiO2 at Room Temperature.
Entry
Run
Yield of 4a (%)
1
2
3
4
5
6
7
1
2
3
4
5
6
7
90
88
86
81
79
77
77
Isolated yield.
tracted much attention in recent years. PPA/SiO2 is easily
recovered from the reaction mixture by filtration. The recov-
ered PPA/SiO2 is regenerated by washing and drying, and
can be used for a subsequent reaction. The results of recy-
cling are summarized in Table 4. As can be seen from Table
3, it was possible to recycle PPA/SiO2 up to seven times and
4a was obtained in satisfactory yield (Table 4, entry 7).
EXPERIMENTAL
Melting points and IR spectra of all compounds were
measured on an Electrothermal 9100 apparatus and a JASCO
FT/IR-460 Plus spectrometer respectively. The H and 13C
1
spectra were obtained on Bruker DRX-250 and 400 Avance
instruments with CDCl3 as solvent. Elemental analyses were

202 Letters in Organic Chemistry, 2013, Vol. 10, No. 3
Doostmohammadi and Hazeri
(t, J = 7.2 Hz, CH3), 4.24 (q, J = 7.2 Hz, CH2), 5.82 (s, 1H,
benzylic), 7.17 (t, J = 7.2 Hz, 1H), 7.32-7.47 (m, 6H, aro-
matic), 7.59 (d, J = 8 , 2H), 9.0 (br, 1H, NH); 13C NMR (100
MHz, CDCl3) ꢁ: 164.6 and 162.5 (ester CO), 156.8, 140.8,
135.7, 132.5, 129.2, 128.3, 126.3, 122.1, 118.1 and 112.6
(aromatic C), 112.2 (CN), 61.6 (ethoxy CH2), 60.8 (benzylic
C), 14.0 (ethoxy CH3). MS m/z (%): 93 (17), 119 (9), 155
(70), 183 (29), 228 (13), 275 (59), 302 (14), 348 (M+, 100);
Anal. calcd. for C20H16N2O4: C, 68.96; H, 4.63; N, 8.04.
Found: C, 69.10; H, 4.69; N, 8.11.
performed using a Heraeus CHN-O-Rapid analyzer. Mass
spectra were recorded on an Agilent Technology (HP) spec-
trometer operating at an ionization potential of 70 eV. All
reagents and solvents obtained from Fluka and Merck were
used without further purification.
General procedures for synthesis of furan-2(5H)-one
4. The mixture of aldehyde (1 mmol), amine (1 mmol),
dialkylacetylenedicarboxylate (1 mmol) and silica gel-
supported polyphosphoric acid (0.15g) was stirred in ethanol
as solvent at room temperature. After completion of the
reaction (monitored by thin-layer chromatograohy, TLC)
CH2Cl2 was added and the mixture stirred for 5 min. The
catalyst was filtrated and the filtrate dichloromethane
solution was concentrated. The obtained solid was washed
with ethanol to obtain a pure product.
CONFLICT OF INTEREST
The author(s) confirm that this article content has no con-
flict of interest.
(Compound 4a). Methyl 2,5-dihydro-5-oxo-2-phenyl-4-
ACKNOWLEDGEMENTS
(phenylamino)furan-3-carboxylate White solid: 0.284
g
(92%); mp 195-196 °C; IR (KBr): 3260, 3208, 1702, 1661
We gratefully acknowledge financial support from the
Research Council of the University of Sistan and Balu-
chestan.
1
cm–1; H NMR (400 MHz, CDCl3) ꢁ :3.77 (s, 3H, OCH3),
5.76 (s, 1H, benzylic), 7.13 (t, J = 7.3 Hz, 1H), 7.24-7.31 (m,
6H), 7.52 (d, J = 8 Hz, 2H), 8.90 (br, 1H, NH); 13C NMR
(100 MHz, CDCl3) ꢁ: 165.3 and 162.7 (ester CO), 156.3,
136.1, 134.9, 129.0, 128.7, 128.6, 127.4, 125.9, 122.3 and
112.8 (aromatic C), 61.6 (methoxy C), 52.1(benzylic C); MS
m/z (%): 57(100), 97(75), 152(24), 213(51), 240(39),
250(33), 309(M+, 44); 61.60, 52.10; MS (positive mode):
Anal. calcd. for C18H15NO4: C, 69.89; H, 4.89; N, 4.53.
Found: C, 70.08; H, 4.97; N, 4.60
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