Preparation of 3,4,5-substituted furan-2(5H)-ones using aluminum hydrogen sulfate as an efficient catalyst

Article abstract of DOI:10.1016/j.crci.2013.06.009

Various derivatives of 3,4,5-substituted furan-2(5H)-ones have been readily prepared by using aluminum hydrogen sulfate [Al(HSO₄)₃] as an efficient catalyst in good yields and milder reaction conditions. The versatility of this protocol has been demonstrated with various substituted furan-2(5H)-ones.

Full text of DOI:10.1016/j.crci.2013.06.009

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Full paper/Memoire
Preparation of 3,4,5-substituted furan-2(5H)-ones using
aluminum hydrogen sulfate as an efficient catalyst
Mohammad Reza Mohammad Shafiee a, Syed Sheik Mansoor b,
c
Majid Ghashang a, , Abbas Fazlinia
*
a Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University, P.O. Box: 517, Najafabad, Esfahan, Iran
b Research Department of Chemistry, Bioactive Organic Molecule Synthetic Unit, C. Abdul Hakeem College, Melvisharam, 632 509 Tamil
Nadu, India
c Department of Chemistry, Neyriz Branch, Islamic Azad University, Neyriz, Iran
A R T I C L E I N F O
A B S T R A C T
Article history:
Various derivatives of 3,4,5-substituted furan-2(5H)-ones have been readily prepared by
using aluminum hydrogen sulfate [Al(HSO4)3] as an efficient catalyst in good yields and
milder reaction conditions. The versatility of this protocol has been demonstrated with
various substituted furan-2(5H)-ones.
Received 11 April 2013
Accepted after revision 25 June 2013
Available online xxx
ß 2013 Acade´mie des sciences. Published by Elsevier Masson SAS. All rights reserved.
Keywords:
3,4,5-substituted furan-2(5H)-one
Al(HSO4)3
Acetylenic esters
Butenolides
1. Introduction
of furan scaffolds are in demand by organic chemists.
Among the various furan derivatives, butenolides have
Multi-component reactions (MCRs) have gained much
attention due to their ability in facile execution and
productivity [1]. MCRs based on the use of acetylenic
esters as starting material has gained much importance in
organic synthesis, partly because of the diverse types of
clinical and pharmacological activity associated with the
products of this reaction [2–6]. Of all kinds of MCRs based
on the use of acetylenic esters, methods to synthesize
furan derivatives were considered as the most versatile
ones for chemical construction of poly-substituted furans
[7–11].
Substituted furan derivatives are fundamentally impor-
tant heterocyclic molecules and are present in many
natural and medicinal structures [12,13]. They can be used
as valuable intermediates for the construction of hetero-
cycles in organic synthesis. Thus, efforts for the synthesis
appeared in the literature as interesting components for
the construction of natural and pharmacological com-
pounds. These skeletons show a wide range of biological
activities such as antimicrobial [14], antifungal [15], anti-
inflammatory [16], anticancer [17] and anti-viral HIV-1
[18] activities. Due to this wide range of abundance and
applicability, various approaches toward substituted
butenolides have been developed, which involve the use
of organo-lithium [19], boronic acids [20,21], transition-
metal catalysts such as Pd(OAc)2 [22], Ru [23], Cu(II) [24],
AuCl [25], and secondary amines [26]. However, many of
these methods involve the use of expensive catalysts and
hazardous reagents in stoichiometric amounts.
A new route to the synthesis of furan skeletons was
developed by Murthy et al. via the multi-component
reaction of aromatic amines, aldehydes and acetylenic
esters, which lead to the preparation of 3,4,5-substituted
furan-2(5H)-one derivatives using
b-cyclodextrin as a
catalyst in water [27]. Recently, Nagarapu et al. reported
that SnCl2 can efficiently catalyze this reaction [28].
*
Corresponding author.
E-mail address: ghashangmajid@gmail.com (M. Ghashang).
1631-0748/$ – see front matter ß 2013 Acade´mie des sciences. Published by Elsevier Masson SAS. All rights reserved.
http://dx.doi.org/10.1016/j.crci.2013.06.009
Please cite this article in press as: Shafiee MRM, et al. Preparation of 3,4,5-substituted furan-2(5H)-ones using
aluminum hydrogen sulfate as an efficient catalyst. C. R. Chimie (2013), http://dx.doi.org/10.1016/j.crci.2013.06.009

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H
2.3.2. Methyl 4-(p-tolylamino)-2,5-dihydro-5-oxo-2-p-
tolylfuran-3-carboxylate (3a)
Ar
O
N
CO2R
RO2C
Ar'
Al(HSO4)3
EtOAc; r.t.
ArNH2 +
1H NMR (400 MHz, CDCl3): 2.28 (s, 3H), 2.54 (s, 3H),
3.77 (s, 3H), 5.71 (s, 1H), 7.07 (d, J = 8.3 Hz, 2H), 7.15 (d,
J = 8.3 Hz, 2H), 7.29 (d, J = 8.3 Hz, 2H), 7.39 (d, J = 8.3 Hz,
+ Ar'CHO
RO2C
O
2H), 8.89 (s, 1H, NH) ppm; 13C NMR (100 MHz, CDCl3)
d:
Scheme 1. Preparation of 3,4,5-substituted furan-2(5H)-one derivatives.
20.7, 34.2, 51.8, 61.5, 112.9, 122.3, 125.6, 126.7, 129.7,
131.8, 133.5, 135.6, 151.3, 156.1, 162.8, 165.3 ppm IR
(KBr): 3222, 2954, 1682, 1613, 1515, 1463, 1309, 1255,
1137, 1032, 994, 896, 848, 747 cmÀ1; found: C, 71.27; H,
5.77; N, 4.21 C20H19NO4; requires: C, 71.20; H, 5.68; N,
4.15%.
However, as the existing literature reports that the
reaction performance is somewhat vitiated by its time-
consuming aspects, the development of a new, efficient
and green approach for the preparation of substituted
furan-2(5H)-ones is highly desirable. In view of the above
and as a part of our ongoing program on multi-component
reactions [29], an efficient and convenient synthesis of
3,4,5-substituted furan-2(5H)-one derivatives has been
accomplished by a multi-component reaction between
aromatic amines, aldehydes and acetylenic esters, using
Al(HSO4)3 as an efficient catalyst, with good yields
(Scheme 1).
2.3.3. Ethyl 4-(p-tolylamino)-2,5-dihydro-5-oxo-2-p-
tolylfuran-3-carboxylate (4a)
1H NMR (400 MHz, CDCl3): 1.26 (t, J = 6.8 Hz, 3H), 2.28
(s, 3H), 2.54 (s, 3H), 4.08 (q, J = 6.8 Hz, 2H), 5.72 (s, 1H), 7.08
(d, J = 8.2 Hz, 2H), 7.14 (d, J = 8.2 Hz, 2H), 7.30 (d, J = 8.2 Hz,
2H), 7.41 (d, J = 8.3 Hz, 2H), 8.89 (s, 1H, NH) ppm; 13C NMR
(100 MHz, CDCl3)
d: 14.3, 20.6, 34.1, 51.6, 61.6, 112.9,
122.4, 125.6, 126.8, 129.6, 131.9, 133.5, 135.6, 151.2, 156.1,
162.6, 165.1 ppm IR (KBr): 3224, 3026, 2951, 1703, 1681,
1615, 1511, 1461, 1310, 1254, 1138, 1030, 994, 848,
745 cmÀ1; found: C, 71.88; H, 6.09; N, 4.05 C21H21NO4;
requires: C, 71.78; H, 6.02; N, 3.99%.
2. Experimental
2.1. Reagents and instrumentation
2.3.4. Methyl 4-(p-tolylamino)-2-(4-chlorophenyl)-2,5-
dihydro-5-oxofuran-3-carboxylate (5a)
All reagents were purchased from Merck and Aldrich
and used without further purification. All yields refer to
isolated products after purification. The NMR spectra were
recorded on a Bruker Avance DPX 400 MHz instrument.
The spectra were measured in CDCl3 relative to TMS
(0.00 ppm). IR spectra were recorded on a PerkinElmer 781
spectrophotometer. Elemental analysis was performed on
a Heraeus CHN-O-Rapid analyzer. Melting points were
determined in open capillaries with a Buchi B-510 melting
point apparatus. TLC was performed on Polygram SIL G/UV
254 silica gel plates.
1H NMR (400 MHz, CDCl3): 2.29 (s, 3H), 3.88 (s, 3H),
5.73 (s, 1H), 7.08 (d, J = 8.2 Hz, 2H), 7.16 (d, J = 8.2 Hz, 2H),
7.35 (d, J = 8.5 Hz, 2H), 7.51 (d, J = 8.5 Hz, 2H), 9.02 (s, 1H,
NH) ppm; 13C NMR (100 MHz, CDCl3)
d: 20.3, 51.6, 60.8,
113.0, 122.9, 125.9, 126.8, 128.8, 129.2, 131.4, 134.9, 143.3,
156.1, 162.5, 165.4 IR (KBr): 3218, 2952, 1715, 1684, 1596,
1496, 1456, 1370, 1282, 1232, 1197, 1132, 1092, 1011, 928,
831, 7610 cmÀ1
19H16ClNO4; requires: C, 63.78; H, 4.51; N, 3.91%.
; found: C, 63.89; H, 4.63; N, 4.01
C
2.3.5. Methyl 4-(p-tolylamino)-2-(4-tert-butylphenyl)-2,5-
dihydro-5-oxofuran-3-carboxylate (6a)
2.2. General procedure
1H NMR (400 MHz, CDCl3): 1.27 (s, 9H), 2.27 (s, 3H),
3.76 (s, 3H), 5.70 (s, 1H), 7.09 (d, J = 8.4 Hz, 2H), 7.14 (d,
J = 8.4 Hz, 2H), 7.27 (d, J = 8.4 Hz, 2H), 7.37 (d, J = 8.4 Hz,
To a mixture of aldehyde (1 mmol), aromatic amine
(1 mmol) and acetylenic esters (1 mmol) in ethyl acetate
(5 mL), Al(HSO4)3 (0.05 g) was added as the catalyst, and the
mixture was stirred for an appropriate time at room
temperature. The progress of the reaction was monitored
by TLC. Upon completion, the solvent was concentrated and
the reaction mixture was diluted in CH2Cl2; the catalyst was
isolated by simple filtration, and the crude product was
washed with diethyl ether to afford the pure product.
2H), 8.92 (s, 1H, NH) ppm; 13C NMR (100 MHz, CDCl3)
d:
20.8, 31.1, 34.4, 51.9, 61.2, 112.7, 122.1, 125.4, 126.8,
129.4, 131.7, 133.6, 135.4, 151.2, 155.9, 162.7, 165.2 ppm
IR (KBr): 3223, 2951, 1710, 1675, 1511, 1467, 1375, 1305,
1210, 1139, 825, 771 cmÀ1; found: C, 72.89; H, 6.71; N,
3.75 C23H25NO4; requires: C, 72.80; H, 6.64; N, 3.69%.
2.3.6. Ethyl 4-(p-tolylamino)-2-(4-tert-butylphenyl)-2,5-
dihydro-5-oxofuran-3-carboxylate (7a)
2.3. Selected data
1H NMR (400 MHz, CDCl3): 1.25-1.29 (m, 12H), 2.28 (s,
3H), 4.05 (q, J = 6.7 Hz, 2H), 5.70 (s, 1H), 7.08 (d, J = 8.3 Hz,
2H), 7.13 (d, J = 8.3 Hz, 2H), 7.27 (d, J = 8.3 Hz, 2H), 7.38 (d,
J = 8.3 Hz, 2H), 8.91 (s, 1H, NH) ppm; 13C NMR (100 MHz,
2.3.1. Methyl 4-(p-tolylamino)-2,5-dihydro-5-oxo-2-
phenylfuran-3-carboxylate (1a)
1H NMR (400 MHz, CDCl3): 2.25 (s, 3H), 3.81 (s, 3H),
5.69 (s, 1H), 7.06 (d, J = 8.1 Hz, 2H), 7.14-7.38 (m, 7H), 8.93
(s, 1H, NH) ppm; IR (KBr): 3226, 2951, 1706, 1679, 1514,
1466, 1378, 1305, 1235, 1202, 1139, 998, 829, 811,
772 cmÀ1; found: C, 70.69; H, 5.38; N, 4.39 C19H17NO4;
requires: C, 70.58; H, 5.30; N, 4.33%.
CDCl3)
d: 14.5, 20.8, 31.2, 34.5, 51.8, 61.5, 112.7, 122.3,
125.4, 126.7, 129.5, 131.9, 133.7, 135.4, 151.5, 156.2, 162.6,
165.4 ppm IR (KBr): 3221, 3024, 2950, 1709, 1675, 1512,
1375, 1212, 1139, 826, 771 cmÀ1; found: C, 73.35; H, 6.99;
N, 3.64 C24H27NO4; requires: C, 73.26; H, 6.92; N, 3.56%.
Please cite this article in press as: Shafiee MRM, et al. Preparation of 3,4,5-substituted furan-2(5H)-ones using
aluminum hydrogen sulfate as an efficient catalyst. C. R. Chimie (2013), http://dx.doi.org/10.1016/j.crci.2013.06.009

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3
Table 1
2.3.7. Methyl 4-(4-chlorophenylamino)-2,5-dihydro-5-oxo-
2-p-tolylfuran-3-carboxylate (8a)
Optimization of the reaction conditions for the synthesis of methyl 4-(p-
tolylamino)-2,5-dihydro-5-oxo-2-phenylfuran-3-carboxylate.
1H NMR (400 MHz, CDCl3): 2.55 (s, 3H), 3.83 (s, 3H),
5.75 (s, 1H), 7.07 (d, J = 8.0 Hz, 2H), 7.17 (d, J = 8.0 Hz, 2H),
7.32 (d, J = 8.2 Hz, 2H), 7.45 (d, J = 8.2 Hz, 2H), 8.98 (s, 1H,
Entry Catalyst (g) T (8C) Solvent (5 mL) Time (h) Yield (%)a
1
2
0.05
0.05
0.05
0.05
0.05
0.05
0.05
–
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
r.t.
n–Hexane
CH2Cl2
Et2O
8
8
45
50
65
78
51
55
25
–
NH) ppm; 13C NMR (100 MHz, CDCl3)
d: 20.4, 61.5, 51.6,
3
8
112.9, 123.1, 126.8, 128.4, 128.8, 129.2, 131.4, 134.8, 134.9,
156.3, 162.6, 165.4 IR (KBr): 3219, 2952, 1714, 1684, 1595,
1496, 1456, 1426, 1371, 1338, 1283, 1232, 1197, 1132,
1092, 1011, 928, 831, 805, 760, 711, 699 cmÀ1; found: C,
63.89; H, 4.60; N, 3.99 C19H16ClNO4; requires: C, 63.78; H,
4.51; N, 3.91%.
4
EtOAc
EtOH
8
5
8
6
MeOH
–
8
7
8
8
EtOAc
EtOAc
EtOAc
EtOAc
10
10
6
9
0.025
0.075
0.1
65
77
76
10
11
5
2.3.8. Methyl 4-(4-methoxyphenylamino)-2,5-dihydro-5-
oxo-2-p-tolylfuran-3-carboxylate (10a)
a
Isolated yields.
1H NMR (400 MHz, CDCl3): 2.53 (s, 3H), 3.80 (s, 3H),
5.73 (s, 1H), 6.88 (d, J = 8.8 Hz, 2H), 7.05-7.09 (m, 4H), 7.31
(d, J = 8.8 Hz, 2H), 8.85 (s, 1H, NH) ppm; 13C NMR (100 MHz,
the best results were obtained when 0.05 g of Al(HSO4)3 in
EtOAc as solvent was employed (Table 1, entry 4).
To find out the optimized amount of Al(HSO4)3, the
reaction was carried out by varying the quantity of catalyst
(Table 1, entries 9–11). The maximum yield was obtained
when 0.05 g of catalyst was used (Table 1, entry 4). Further
increase in the amount of Al(HSO4)3 in the mentioned
reaction did not have any significant effect on the product
yield. The results are summarized in Table 1.
CDCl3) d: 19.7, 51.8, 55.3, 61.4, 112.1, 124.6, 125.3, 126.4,
128.1, 128.5, 135.8, 136.4, 144.1, 157.2, 163.4, 165.1 ppm
IR (KBr): 3221, 2950, 1707, 1677, 1513, 1466, 1375, 1304,
1207, 1141, 828, 771 cmÀ1; found: C, 68.09; H, 5.51; N,
4.05 C20H19NO5; requires: C, 67.98; H, 5.42; N, 3.96%.
3. Results and discussion
Next, the scope and efficiency of these procedures were
explored for the synthesis of a wide variety of substituted
3,4,5-substituted furan-2(5H)-ones (Scheme 1, Table 2).
Generally, the results were excellent in terms of yield
and product purity. A series of aromatic aldehydes and
amines were investigated (Table 2, products 1a–17a). In all
cases, aromatic aldehydes containing electron-donating
groups gave shorter times and higher yields than that with
electron-withdrawing groups.
The work-up procedure is very clear-cut; this means
that the products were isolated and purified by simple
filtration and washing with diethyl ether. Our protocol
making use of Al(HSO4)3 during the reaction process is
better than those using hazardous liquid acidic catalysts.
Our initial aim was to develop an efficient one-pot
procedure for the synthesis of 3,4,5-substituted furan-
2(5H)-one derivatives through the reaction of aromatic
amines, aldehydes and acetylenic esters by employing
Al(HSO4)3. Accordingly, the transformation of 4-methyla-
niline, dimethylacetylenedicarboxylate and benzaldehyde
into methyl 4-(p-tolylamino)-2,5-dihydro-5-oxo-2-phe-
nylfuran-3-carboxylate was investigated (Table 1). The
reaction was carried out by using different solvents (Table
1, entries 1–6) or solvent-free conditions (Table 1, entry 7)
at room temperature. Lower yield of the product was
achieved under solvent-free conditions. It was found that
Table 2
Synthesis of 3,4,5-substituted furan-2(5H)-one derivatives (Scheme 1).
Product
Aldehyde
Amine
R
Time (h)
Yield (%)a
1a
Benzaldehyde
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Chloroaniline
4-Chloroaniline
4-Methoxyaniline
Aniline
Me
Et
8
8
78
80
89
90
71
81
80
85
79
86
84
77
86
84
75
70
80
2a
Benzaldehyde
3a
4-Methylbenzaldehyde
4-Methylbenzaldehyde
4-Chlorobenzaldehyde
4-tert-Butylbenzaldehyde
4-tert-Butylbenzaldehyde
4-Methylbenzaldehyde
Benzaldehyde
Me
Et
7
4a
7
5a
Me
Me
Et
10
8
6a
7a
8
8a
Me
Me
Me
Me
Et
10
10
7
9a
10a
11a
12a
13a
14a
15a
16a
17a
4-Methylbenzaldehyde
Benzaldehyde
8
Benzaldehyde
Aniline
9
4-Methylbenzaldehyde
4-Methylbenzaldehyde
4-Chlorobenzaldehyde
2-Chlorobenzaldehyde
2,4-Dichlorobenzaldehyde
Aniline
Me
Et
8
Aniline
8
Aniline
Me
Me
Me
10
12
12
Aniline
Aniline
a
Isolated yields. All known products had been reported previously in the literature and were characterized by comparison of their IR and NMR spectra
with those of authentic samples [27,28].
Please cite this article in press as: Shafiee MRM, et al. Preparation of 3,4,5-substituted furan-2(5H)-ones using
aluminum hydrogen sulfate as an efficient catalyst. C. R. Chimie (2013), http://dx.doi.org/10.1016/j.crci.2013.06.009

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(1998) 7799;
In summary, an efficient protocol for the preparation of
3,4,5-substituted furan-2(5H)-one derivatives was
described. The reactions were carried out under ambient
conditions with short reaction times and produce the
corresponding products in good yields. The present
methodology offers several advantages such as good
yields, simple procedure, shorter reaction times and milder
conditions; moreover, the products were purified without
having resort to chromatography.
(b) G. Grossmann, M. Poncioni, M. Bornand, B. Jolivet, M. Neuburger, U.
Sequin, Tetrahedron 59 (2003) 3237;
(c) L.M. Levy, G.M. Cabrera, J.E. Wright, A.M. Seldes, Phytochemistry 62
(2003) 239.
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Acknowledgments
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We are thankful to the Najafabad Branch, Islamic Azad
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research.
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Please cite this article in press as: Shafiee MRM, et al. Preparation of 3,4,5-substituted furan-2(5H)-ones using
aluminum hydrogen sulfate as an efficient catalyst. C. R. Chimie (2013), http://dx.doi.org/10.1016/j.crci.2013.06.009