Preparation of 3,4,5-substituted furan-2(5H)-ones using HY Zeolite nano-powder as an efficient catalyst

Article abstract of DOI:10.1007/s11164-016-2476-0

Abstract: Some 3,4,5-substituted furan-2(5H)-one derivatives, were obtained in good yields and from the corresponding three-component reaction of aromatic amines, aldehydes, and acetylenic esters by HY Zeolite nano-powder as an efficient catalyst. Graphical Abstract: [Figure not available: see fulltext.]

Full text of DOI:10.1007/s11164-016-2476-0

Res Chem Intermed
DOI 10.1007/s11164-016-2476-0
Preparation of 3,4,5-substituted furan-2(5H)-ones using
HY Zeolite nano-powder as an efficient catalyst
Farzaneh Bahramian1 Abbas Fazlinia2
•
•
Syed Sheik Mansoor3 Majid Ghashang4
Fateme Azimi4 Mohammad Najafi Biregan4
•
•
•
Received: 15 November 2015 / Accepted: 3 February 2016
Ó Springer Science+Business Media Dordrecht 2016
Abstract Some 3,4,5-substituted furan-2(5H)-one derivatives, were obtained in good
yields and from the corresponding three-component reaction of aromatic amines, alde-
hydes, and acetylenic esters by HY Zeolite nano-powder as an efficient catalyst.
Graphical Abstract
H
Ar
O
N
CO2R
+ Ar'CHO
HY Zeolite nano-powder
EtOH, Reflux
RO2C
Ar'
ArNH2
+
RO2C
O
O
R'O
CO2R'
H
N
NH2
N
CHO
HY Zeolite nano-powder
EtOH, Reflux
+
N
R'O2C
+
O
R
R
O
Keywords 3,4,5-Substituted furan-2(5H)-one Á HY Zeolite nano-powder Á
Acetylenic esters Á Butenolides Á 9-Methyl-9H-carbazole-2-carbaldehyde
&
Majid Ghashang
ghashangmajid@gmail.com
1
2
3
Department of Chemistry, Payame Noor University of Estahban, Estahban, Iran
Department of Chemistry, Shiraz Branch, Islamic Azad Univercity, Shiraz, Iran
Research Department of Chemistry, Bioactive Organic Molecule Synthetic Unit, C. Abdul
Hakeem College, Melvisharam, Tamil Nadu 632 509, India
4
Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University,
P.O. Box: 517, Najafabad, Esfahan, Iran
123

F. Bahramian et al.
Introduction
Functionalized furan-2(5H)-ones, generally called butenolides, constitute an important
classofheterocycliccompounds, whichare broadlyfoundinmanynaturalproductsand
drugs [1–7]. Butenolides are of synthetic interest, since they show useful biological
activities such as antimicrobial activity [8, 9], antifungal [10, 11], anti-inflammatory
[12], anticancer [13, 14], and HIV-1 anti-viral activities [15, 16]. On the other hand,
butenolides are versatile building blocks for natural product syntheses. Therefore, the
synthesis of the butenolide scaffolds has gained great importance in organic synthesis,
andmanyorganicandmedicinalchemistshavedevotedtheireffortstothedevelopment
of novel and efficient methods for the synthesis of furan-2(5H)-one derivatives.
Among of the various methods established for the synthesis of different
butenolides, the three-component reaction of aromatic amines, aldehydes, and
acetylenic esters is considered as one of the most versatile and newly routes for the
preparation of 3,4,5-substituted furan-2(5H)-one derivatives. Murthy et al. [17] first
discovered this method and used b-cyclodextrin as an efficient catalyst. Similar
catalytic systems later reported involving the use of SnCl2 [18], ZnO nano-particles
[19], Al(HSO4)3 [20] tetra-n-butylammonium bisulfate [21], and SnO [22].
Although these methods show good yields of substituted furan-2(5H)-ones, further
development of efficient and simple strategies for the preparation of substituted
furan-2(5H)-ones with cheap catalysts is highly desirable.
As a part of our ongoing program for multi-component reactions [23–26], herein we
wish to report an HY Zeolite nano-powder catalyzed synthesis of 3,4,5-substituted
furan-2(5H)-ones via a multi-component reaction of aromatic amines, aldehydes, and
acetylenic esters. This procedure developed a new, efficient, and green approach for
the preparation of substituted furan-2(5H)-ones in good yields (Scheme 1).
Experimental
Reagents and instrumentation
All reagents were purchased from Merck and Aldrich and used without further
purification. Field emission scanning electron microscope (FE-SEM) images were
H
Ar
O
N
CO2R
+ Ar'CHO
HY Zeolite nano-powder
EtOH, Reflux
RO2C
Ar'
ArNH2
+
RO2C
O
O
R'O
CO2R'
H
N
NH2
N
CHO
HY Zeolite nano-powder
EtOH, Reflux
+
N
R'O2C
+
O
R
R
O
Scheme 1 Preparation of 3,4,5-substituted furan-2(5H)-one derivatives
123

Preparation of 3,4,5-substituted furan-2(5H)-ones using…
obtained on a HITACHI S-4160. N2 adsorption measurements of the catalyst were
carried out using Micrometrics adsorption equipment (Quantachrome instrument,
model Nova 2000, USA), N2 (99.99 %) as the analysis gas and the catalyst samples
were slowly heated to 120 °C for 3 h under nitrogen atmosphere. The total pore
volume was obtained from the maximum amount of nitrogen gas adsorbed at partial
pressure P/P0 = 0.999. Dynamic light scattering (DLS) measurement was done
using a Malvern Zetasizer Nano ZS (ZEN 3600) instrument. The NMR spectra were
recorded on a Bruker Avance DPX 400 MHz instrument. The spectra were
measured in DMSO-d6 relative to TMS (0.00 ppm). Melting points were determined
in open capillaries with a BUCHI 510 melting point apparatus. TLC was performed
on silica gel Polygram SIL G/UV 254 plates.
General procedure
Aromatic amine (1 mmol), and acetylenic esters (1 mmol) in ethanol (5 mL), HY
Zeolite nano-powder (0.05 g) was added to a mixture of aldehyde (1 mmol), and the
mixture was stirred for appropriate time at reflux condition. Progress of the reaction
was monitored by TLC. Upon completion, the solvent was concentrated and the
reaction mixture was diluted with CH2Cl2 (20 mL). The solid catalyst was removed
by the filter paper. After evaporation of the solvent (CH2Cl2), the residue was
washed with diethyl ether to afford the pure product.
Selected data
Methyl 2,5-dihydro-2-(9-methyl-9H-carbazol-3-yl)-5-oxo-4-(phenylamino)furan-3-
carboxylate (18a) 1H-NMR (400 MHz, DMSO-d6): 3.74 (s, 3H, OCH3), 3.77 (s,
3H, N-CH3), 6.41 (s, 1H), 7.08 (t, J = 7.8 Hz, 1H), 7.20–7.29 (m, 3H), 7.48–7.61
(m, 7H), 7.90 (s, 1H), 8.94 (s, 1H, NH) ppm; 13C-NMR (100 MHz, DMSO-d6):
30.1, 52.1, 62.1, 109.7, 110.8, 119.5, 120.9, 121.3, 121.8, 123.5, 123.6, 124.7,
125.2, 126.7, 129.2, 129.8, 131.1, 137.4, 141.2, 142.4, 143.1, 163.6, 166.1 ppm;
Found: C, 72.97; H, 5.03; N, 6.90 C25H20N2O4; requires: C, 72.80; H, 4.89; N,
6.79 %.
Ethyl 2,5-dihydro-2-(9-methyl-9H-carbazol-3-yl)-5-oxo-4-(phenylamino)furan-3-
carboxylate (19a) 1H-NMR (400 MHz, DMSO-d6): 1.22 (t, J = 6.9 Hz, 3H),
3.76 (s, 3H, N-CH3), 4.16 (q, J = 6.9 Hz, 2H), 6.40 (s, 1H), 7.08 (t, J = 7.8 Hz,
1H), 7.21–7.29 (m, 3H), 7.48–7.61 (m, 7H), 7.90 (s, 1H), 8.91 (s, 1H, NH) ppm;
13C-NMR (100 MHz, DMSO-d6): 14.6, 30.0, 52.1, 62.2, 109.7, 110.7, 119.4, 120.9,
121.3, 121.8, 123.5, 123.6, 124.7, 125.2, 126.7, 129.2, 129.8, 131.1, 137.3, 141.1,
142.4, 143.1, 163.5, 166.3 ppm; Found: C, 73.35; H, 5.31; N, 6.70 C26H22N2O4;
requires: C, 73.23; H, 5.20; N, 6.57 %.
Methyl 4-(p-tolylamino)-2,5-dihydro-2-(9-methyl-9H-carbazol-3-yl)-5-oxofuran-3-
carboxylate (20a) 1H-NMR (400 MHz, DMSO-d6): 2.24 (s, 3H, CH3), 3.75 (s,
3H, OCH3), 3.76 (s, 3H, N-CH3), 6.39 (s, 1H), 7.09–7.16 (m, 4H), 7.21–7.30 (m,
3H), 7.49–7.60 (m, 3H), 7.90 (s, 1H), 8.90 (s, 1H, NH) ppm; 13C-NMR (100 MHz,
123

F. Bahramian et al.
DMSO-d6): 21.3, 29.9, 51.9, 62.3, 110.0, 110.7, 113.1, 119.5, 120.8, 121.2, 123.7,
123.9, 125.3, 126.7, 129.3, 129.9, 131.4, 132.5, 137.6, 141.0, 142.1, 142.7, 163.1,
166.1 ppm; Found: C, 73.33; H, 5.29; N, 6.68 C26H22N2O4; requires: C, 73.23; H,
5.20; N, 6.57 %.
Ethyl 4-(p-tolylamino)-2,5-dihydro-2-(9-methyl-9H-carbazol-3-yl)-5-oxofuran-3-
carboxylate (21a) 1H-NMR (400 MHz, DMSO-d6): 1.27 (t, J = 6.9 Hz, 3H,
CH3), 2.23 (s, 3H, CH3), 3.76 (s, 3H, N-CH3), 4.16 (q, J = 6.9 Hz, 2H, CH2), 6.38
(s, 1H), 7.09–7.16 (m, 4H), 7.21–7.33 (m, 3H), 7.49–7.60 (m, 3H), 7.79 (s, 1H),
8.89 (s, 1H, NH) ppm; 13C-NMR (100 MHz, DMSO-d6): 14.4, 21.3, 29.6, 60.7,
62.5, 110.1, 110.5, 113.0, 119.5, 120.7, 121.0, 123.7, 123.9, 125.2, 126.4, 129.6,
129.9, 131.3, 132.5, 137.5, 141.0, 142.4, 142.6, 163.2, 166.0 ppm; Found: C, 73.74;
H, 5.57; N, 6.48 C27H24N2O4; requires: C, 73.62; H, 5.49; N, 6.36 %.
Methyl 4-(4-chlorophenylamino)-2,5-dihydro-2-(9-methyl-9H-carbazol-3-yl)-5-oxo-
furan-3-carboxylate (22a) 1H-NMR (400 MHz, DMSO-d6): 3.73 (s, 3H, OCH3),
3.75 (s, 3H, N-CH3), 6.40 (s, 1H), 7.20–7.30 (m, 3H), 7.44 (d, J = 7.9 Hz, 2H),
7.49–7.61 (m, 3H), 7.77 (d, J = 7.9 Hz, 2H), 7.80 (s, 1H) 8.98 (s, 1H, NH) ppm;
13C-NMR (100 MHz, DMSO-d6): 29.7, 52.3, 62.7, 110.2, 110.7, 119.5, 120.1,
120.7, 121.0, 123.3, 123.7, 125.2, 126.4, 129.4, 129.7, 130.0, 131.4, 137.4, 141.1,
142.0, 142.6, 163.5, 166.3 ppm; Found: C, 67.31; H, 4.44; N, 6.37 C25H19ClN2O4;
requires: C, 67.19; H, 4.29; N, 6.27 %.
Ethyl 4-(4-chlorophenylamino)-2,5-dihydro-2-(9-methyl-9H-carbazol-3-yl)-5-oxo-
furan-3-carboxylate (23a) 1H-NMR (400 MHz, DMSO-d6): 1.26 (t, J = 6.9 Hz,
3H, CH3), 3.76 (s, 3H, N-CH3), 4.17 (q, J = 6.9 Hz, 2H, CH2), 6.39 (s, 1H),
7.20–7.30 (m, 3H), 7.45 (d, J = 7.9 Hz, 2H), 7.49–7.61 (m, 3H), 7.77 (d,
J = 7.9 Hz, 2H), 7.79 (s, 1H) 8.97 (s, 1H, NH) ppm; 13C-NMR (100 MHz, DMSO-
d6): 14.5, 29.6, 60.7, 62.6, 110.0, 110.6, 119.6, 120.2, 120.8, 121.0, 123.2, 123.6,
125.3, 126.4, 129.3, 129.6, 130.1, 131.3, 137.4, 141.0, 142.1, 142.5, 163.6,
166.5 ppm; Found: C, 67.92; H, 4.74; N, 6.21 C26H21ClN2O4; requires: C, 67.75; H,
4.59; N, 6.08 %.
Methyl 4-(4-methoxyphenylamino)-2,5-dihydro-2-(9-methyl-9H-carbazol-3-yl)-5-
oxofuran-3-carboxylate (24a) 1H-NMR (400 MHz, DMSO-d6): 3.72 (s, 3H,
OCH3), 3.74 (s, 3H, OCH3), 3.76 (s, 3H, N-CH3), 6.40 (s, 1H), 6.67 (d,
J = 8.0 Hz, 2H), 7.10 (d, J = 8.0 Hz, 2H), 7.20–7.30 (m, 3H), 7.49–7.60 (m, 3H),
7.80 (s, 1H), 8.92 (s, 1H, NH) ppm; 13C-NMR (100 MHz, DMSO-d6): 29.6, 52.7,
55.9, 62.8, 109.9, 110.4, 114.7, 119.7, 120.4, 120.7, 121.0, 123.2, 123.5, 125.2,
126.5, 129.7, 131.4, 137.5, 141.0, 142.2, 142.6, 157.4, 163.7, 166.2 ppm; Found: C,
70.74; H, 5.16; N, 6.50 C26H22N2O5; requires: C, 70.58; H, 5.01; N, 6.33 %.
Ethyl 4-(4-methoxyphenylamino)-2,5-dihydro-2-(9-methyl-9H-carbazol-3-yl)-5-ox-
ofuran-3-carboxylate (25a) 1H-NMR (400 MHz, DMSO-d6): 1.27 (t,
J = 6.9 Hz, 3H, CH3), 3.76 (s, 3H, N-CH3), 3.78 (s, 3H, OCH3), 4.17 (q,
J = 6.9 Hz, 2H, CH2), 6.40 (s, 1H), 6.68 (d, J = 8.0 Hz, 2H), 7.11 (d, J = 8.0 Hz,
2H), 7.21–7.29 (m, 2H), 7.34 (d, J = 8.0 Hz, 1H), 7.49–7.60 (m, 3H), 7.79 (s, 1H),
123

Preparation of 3,4,5-substituted furan-2(5H)-ones using…
Fig. 1 FE-SEM micrograph of HY Zeolite nano-powder
Table 1 Specific surface area, total pore volume and average pore diameter of HY Zeolite nano-powder
Specific surface area (m2/g)
Pore diameter (nm)
71.21
Pore volume (cc/g)
0.172
559
8.90 (s, 1H, NH) ppm; 13C-NMR (100 MHz, DMSO-d6): 14.7, 29.6, 55.7, 61.2,
62.2, 110.1, 110.6, 114.8, 119.9, 120.5, 120.8, 121.1, 123.3, 123.6, 125.3, 126.4,
129.5, 131.5, 137.6, 141.1, 142.3, 142.5, 157.0, 163.8, 166.1 ppm; Found: C, 71.21;
H, 5.42; N, 6.25 C27H24N2O5; requires: C, 71.04; H, 5.30; N, 6.14 %.
Result and discussion
NaY zeolite nano-powder was prepared according to the procedures described by
Wang and Yan [27]. The as prepared NaY zeolite nano-powder was converted to
HY zeolite nano-powder following the procedure described by Ramli and Amin
[28].
The morphological evolution of the HY Zeolite nano-powder was further studied
using FE-SEM images of calcined powder and the results are revealed in Fig. 1. As
shown in Fig. 1 the particles are relatively homogeneous in size and shape and are
uniform spheres.
The specific surface area measurements of the HY Zeolite nano-powder were
evacuated by BET method, and also the total pore volume and average pore
diameter were determined at 200 °C for 300 min. The results are given in Table 1.
These results show that the catalyst has a good specific surface area. The average
diameter of the nanoparticles is comparable with those obtained from FE-SEM
technique.
123

F. Bahramian et al.
Fig. 2 Particle size distribution of HY Zeolite nano-powder
The dynamic light scattering (DLS) analysis was used to determine the particle size
distribution of HY Zeolite nano-powder. Before analysis the sample was diluted in water
(0.5 g L-1) and sonicated for 2 h. Figure 2 shows the size distribution of nano-powder.
Focusing on the results, the intensity-average diameter determined by DLS is about 73 nm.
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 HY Zeolite nano-powder.
Accordingly, the transformation of 4-methylaniline, dimethylacetylenedicarboxy-
late, and benzaldehyde into methyl 4-(p-tolylamino)-2,5-dihydro-5-oxo-2-phenyl-
furan-3-carboxylate was investigated (Table 2). The reaction was carried out by the
Table 2 Optimization of the reaction condition in the synthesis of methyl 4-(p-tolylamino)-2,5-dihydro-
5-oxo-2-phenylfuran-3-carboxylate
Entry
Catalyst (g)
T (°C)
Solvent (5 mL)
Time (h)
Yield (%)a
1
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
24
24
24
24
15
15
24
24
15
12
10
TRACE
2
TRACE
25
3
4
EtOAc
EtOH
MeOH
–
65
5
76
6
75
7
20
8
EtOH
EtOH
EtOH
EtOH
–
9
0.025
0.075
0.1
68
10
11
a
77
73
Isolated yields
123

Preparation of 3,4,5-substituted furan-2(5H)-ones using…
Table 3 Synthesis of 3,4,5-substituted furan-2(5H)-one derivatives (Scheme 1)
Product Aldehyde
Amine
R
Time Yield M.p. (°C)
(h)
(%)a [lit M.p.]ref.
1a
Benzaldehyde
4-Methylaniline
Me 15
76
176–178
[173–175]17
2a
3a
4a
5a
6a
7a
8a
9a
10a
11a
Benzaldehyde
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Methylaniline
4-Chloroaniline
4-Chloroaniline
4-Methoxyaniline
Aniline
Et
Me 10
Et 12
15
80
85
90
76
89
85
85
70
88
80
181–183 [–]13
179–181 [–]16
189–191 [–]16
203–205 [–]16
211–213 [–]16
216–218 [–]16
174–176 [–]16
167–169 [–]16
186–188 [–]16
4-Methylbenzaldehyde
4-Methylbenzaldehyde
4-Chlorobenzaldehyde
4-tert-Butylbenzaldehyde
4-tert-Butylbenzaldehyde
4-Methylbenzaldehyde
Benzaldehyde
Me 15
Me 10
Et
12
Me 15
Me 15
Me 10
Me 15
4-Methylbenzaldehyde
Benzaldehyde
197–199
[195–196]17
12a
13a
14a
15a
Benzaldehyde
Aniline
Aniline
Aniline
Aniline
Et
Me 12
Et 15
15
74
87
84
77
201–203 [–]13
177–178 [–]16
180–182 [–]13
4-Methylbenzaldehyde
4-Methylbenzaldehyde
4-Chlorobenzaldehyde
Me 15
150–152
[148–151]18
16a
2-Chlorobenzaldehyde
Aniline
Me 20
70
274–276
[274–276]18
17a
18a
2,4-Dichlorobenzaldehyde
Aniline
Aniline
Me 20
Me 15
83
89
286–288 [–]16
9-Methyl-9H-carbazole-3-
carbaldehyde
291–293 [new
product]
19a
20a
21a
22a
23a
24a
25a
a
9-Methyl-9H-carbazole-3-
carbaldehyde
Aniline
Et
Me 15
Et 15
Me 20
Et 20
Me 15
Et 15
17
84
93
87
79
77
86
80
283–285 [new
product]
9-Methyl-9H-carbazole-3-
carbaldehyde
4-Methylaniline
4-Methylaniline
4-Chloroaniline
4-Chloroaniline
4-Methoxyaniline
4-Methoxyaniline
277–279 [new
product]
9-Methyl-9H-carbazole-3-
carbaldehyde
285–287 [new
product]
9-Methyl-9H-carbazole-3-
carbaldehyde
[300 [new
product]
9-Methyl-9H-carbazole-3-
carbaldehyde
[300 [new
product]
9-Methyl-9H-carbazole-3-
carbaldehyde
289–291 [new
product]
9-Methyl-9H-carbazole-3-
carbaldehyde
290–292 [new
product]
Isolated yields. All known products have been reported previously in the literature and were charac-
terized by comparison of NMR spectra with authentic samples [17–21]
using of different solvents (Table 2, Entries 1–6) or solvent-free condition (Table 2,
Entry 7) at room temperature. The lower yield of product was achieved under
solvent-free condition. It was found that the best results were obtained when 0.05 g
of HY Zeolite nano-powder in EtOH as a solvent was employed (Table 2, Entry 5).
123

F. Bahramian et al.
To find the optimal amount of HY Zeolite nano-powder, the reaction was carried
out by varying amount of the catalyst (Table 2, Entries 9–11). Maximum yield was
obtained when 0.05 g of catalyst was used (Table 2, Entry 5). A further increase in
the amount of HY Zeolite nano-powder in mentioned reaction did not have any
significant effect on the product yield. The results are summarized in Table 2.
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 3).
Generally, the results were excellent in terms of yields and product purity. A
series of aromatic aldehydes and amines were investigated (Table 3, products 1a–
25a). In all cases aromatic aldehydes containing electron-donating groups gave
shorter time and higher yields than that with electron-withdrawing groups. The
results indicated that in contrast with para-substituted substrates, the reaction was
more sluggish when ortho-substituted substrates such as 2-chlorobenzaldehyde was
used as the starting materials (Table 3, products 16a and 17a). The probable reason
for this phenomenon may be explained that the ortho-position has more steric
hindrance effects on the reaction centers. Furthermore, when 4-chloroaniline was
examined the target compounds were obtained in good yields, but in longer reaction
times (Table 3, products 8a and 9a). In contrast with 4-methylaniline or
4-methoxyaniline, 4-chloroaniline is a considerably less reactive nucleophile. The
reaction of 9-methyl-9H-carbazole-3-carbaldehyde and different aromatic amines
proceeds smoothly to obtain product 18a–25a in good yields.
The work-up procedure is very clear-cut; that is, the products were isolated and
purified by simple filtration and washing with diethyl ether. Our protocol has been
used from HY Zeolite nano-powder during the reaction process, making it superior
to the reactions that use hazardous liquid acidic catalysts.
Conclusion
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 and the
products were purified without resorting to chromatography.
Acknowledgments We are thankful to the Najafabad Branch, Islamic Azad University research council
for partial support of this research.
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