Magnetically recyclable copper modified GO/Fe3O4 catalyst for efficient synthesis of quinazolinones

Article abstract of DOI:10.1016/j.cclet.2016.01.055

A series of bioactive quinazolinones were effectively synthesized by the condensation of halide benzamide with amino acid using magnetically recyclable GO/Fe₃O₄-CuI as catalyst. Magnetic GO/Fe₃O₄-CuI was prepared via a simple chemical method and characterized by FTIR, powder XRD, and SEM. This heterogeneous copper catalyst can be easily separated from reaction mixtures by an external permanent magnet and reused without any obvious loss in activity which shows its applicability as a reusable and promising catalyst for quinazolinones synthesis.

Full text of DOI:10.1016/j.cclet.2016.01.055

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CCLET 3583 1–5
Chinese Chemical Letters xxx (2016) xxx–xxx
Contents lists available at ScienceDirect
Chinese Chemical Letters
journal homepage: www.elsevier.com/locate/cclet
1
2
Original article
3
4
Magnetically recyclable copper modified GO/Fe3O4 catalyst for
efficient synthesis of quinazolinones
*
Q1 Lu-Lu Kong, Li-Yan Fan
5
6
Department of Chemistry, Tongji University, Shanghai 200092, China
A R T I C L E I N F O
A B S T R A C T
Article history:
A series of bioactive quinazolinones were effectively synthesized by the condensation of halide
benzamide with amino acid using magnetically recyclable GO/Fe3O4–CuI as catalyst. Magnetic
GO/Fe3O4–CuI was prepared via a simple chemical method and characterized by FTIR, powder XRD,
and SEM. This heterogeneous copper catalyst can be easily separated from reaction mixtures by an
external permanent magnet and reused without any obvious loss in activity which shows its applicability
as a reusable and promising catalyst for quinazolinones synthesis.
Received 23 December 2015
Received in revised form 9 January 2016
Accepted 25 January 2016
Available online xxx
Keywords:
ß 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
Published by Elsevier B.V. All rights reserved.
Quinazolinones
GO/Fe3O4–CuI
Magnetically
Recyclable
Heterogeneous
7
8
1. Introduction
magnetic nanoparticles supported on various materials for 30
recovery have provided new ways to develop recyclable catalyst 31
9
Recently, there has been growing interest in transition metal-
catalyzed C–N and C–C bond forming processes [1]. In particular,
the copper-catalyzed Ullmann-type N-arylations have received
enormous attention and have been widely used to prepare
quinazolinones derivatives [2], whose subunits are extensively
used in medicinal chemistry as a pharmacophore [3], with
applications such as hypnotic, sedative, analgesic, antibacterial,
and antitumor agents [4], or to modify known bioactive molecules
and to potentiate their biological activities [5].
Generally, copper salts have been used as homogeneous
catalyst systems to catalyze synthesis of quinazolinones deriva-
tives from ortho-amino- or-nitrobenzoic acid derivatives, aryl
halides [6]. Although homogeneous copper catalysts have many
advantages, such as high turnover number, good activity, and good
selectivity [7], they are difficult to separate from reaction mixtures
and reuse. Furthermore, the residual copper metal along with the
final products may cause serious problems in the synthesis of
pharmaceuticals [8]. In light of these problems, various catalysts
supports have been explored, such as polymers [9], zeolite [10] and
mesoporous particles [11] that can be efficiently reused while
keeping the inherent activity of the catalytic center. In recent years,
[12].
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It is well known that graphene oxide (GO), one of the most 33
important derivatives of graphene, has a unique planar struc- 34
ture[13], huge surface area (2630 m2 gÀ1) [14], and a variety of 35
oxygen-containing functional groups [15], which renders it a good 36
candidate for supporting other functional materials. What’s more, 37
the acidic and oxidative nature of these oxygen functionalities 38
allow it to function as a solid acid catalyst or green oxidant [16]. 39
In this study, we prepared a magnetically recyclable heteroge- 40
neous catalyst GO/Fe3O4–CuI for the synthesis of quinazolinones 41
by the condensation of halide benzamide with amino acid, which is 42
rarely reported [17]. The catalyst gave the desired products in good 43
yields and could be reused several times without any loss of its 44
catalytic activity, which showed its applicability as a reusable and 45
promising catalyst for quinazolinones synthesis.
46
2. Experimental
47
48
2.1. Sample preparation procedures
GO was synthesized by natural graphite powder oxidation 49
according to the Hummers method [18]. GO (200 mg) was 50
dispersed in 60 mL of 1-methyl-2-pyrrolidone with ultrasonica- 51
tion for 1 h [19], and the mixture was heated to 190 8C under 52
nitrogen atmosphere (Scheme 1). Fe(acac)3 (1.413 g) was dissolved 53
*
Corresponding author.
E-mail address: Fanly@tongji.edu.cn (L.-Y. Fan).
http://dx.doi.org/10.1016/j.cclet.2016.01.055
1001-8417/ß 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
Please cite this article in press as: L.-L. Kong, L.-Y. Fan, Magnetically recyclable copper modified GO/Fe3O4 catalyst for efficient synthesis
of quinazolinones, Chin. Chem. Lett. (2016), http://dx.doi.org/10.1016/j.cclet.2016.01.055

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L.-L. Kong, L.-Y. Fan / Chinese Chemical Letters xxx (2016) xxx–xxx
Scheme 1. Preparation of GO/Fe3O4–CuI catalyst and magnetic separation of GO/Fe3O4–CuI catalyst from water.
54
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57
58
59
60
61
62
63
64
65
66
67
in 40 mL of 1-methyl-2-pyrrolidone and then dropped into the GO
solution under stirring for 2 h. After the reaction finished and
cooled to room temperature, the precipitate was separated by
magnet and dispersed in ethanol. Finally, the resulting black
powder was washed several times with acetone and vacuum dried
at 45 8C overnight.
The obtained GO/Fe3O4 (0.50 g) and CuI (0.25 g) were dispersed
in 50 mL ethanol under nitrogen atmosphere (Scheme 1). Then the
mixture was stirred at 80 8C overnight. The GO/Fe3O4–CuI powder
was retrieved by an external permanent magnet, and washed with
deionized water and ethanol. Finally, the GO/Fe3O4–CuI powder
was dried under vacuum at 45 8C overnight for further use. The
prepared GO/Fe3O4–CuI was characterized by FTIR, powder XRD,
and SEM. The doped concentration of CuI was detected by ICP–AES.
SEM observation was also undertaken to characterize the
morphologies of the GO/Fe3O4 and GO/Fe3O4–CuI composites. As is
shown in Fig. 3a, GO/Fe3O4 sheets show the sheet-like structure
with smooth surfaces and wrinkled edges. GO/Fe3O4–CuI sheets
present similar morphology with the parent GO/Fe3O4. CuI
composites are uniformly distributed on the surface of GO/
Fe3O4–CuI sheets. ICP–AES detected the CuI doped concentration is
up to 10.1 wt% which implies CuI successfully doped on the GO/
Fe3O4 sheets.
To demonstrate its activity for the synthesis of quinazolinones
derivatives, the reaction of 2-iodobenzamide 1a and 2-aminoiso-
valeric acid 1b was used as a model reaction catalyzed by magnetic
GO/Fe3O4–CuI. Clearly, the results in Table 1 show that the reaction
could be catalyzed by several copper salts. While with the amount
of copper was 0.03 equivalent immobilized on GO/Fe3O4, the
reaction went smoothly with a respective high productivity
(compare entries 2–8, Table 1). To further obtain the optimal
100
101
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103
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105
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110
111
112
113
114
115
116
68
69
2.2. Typical procedure for the condensation synthesis of
quinazolinones
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76
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78
2-Iodobenzamide 1a (1.0 equiv.), 2-aminoisovaleric acid 2a
(3.0 equiv.), Cs2CO3 (3.0 equiv.) and GO/Fe3O4–CuI (Cu+
0.03 equiv.) were added to DMSO/ethylene glycol (60:1, v/v) in
a round bottom flask. The reaction was monitored by TLC. The
product was purified by column chromatography with petroleum
ether/ethyl acetate (3:1, v/v) to give pure white solid 3a. Other
products were synthesized through the same procedure and
characterized by 1H NMR and 13C NMR. Their molecular masses
were determined by HRMS.
GO
1730
1622 1230
1056
580
GO/Fe3O4
GO/Fe3O4-CuI
3370
79
3. Results and discussion
4000 3500 3000 2500 2000 1500 1000 500
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81
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90
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93
94
95
96
97
98
99
Fourier-transform infrared spectroscopy (FTIR) spectra of GO,
GO/Fe3O4, and GO/Fe3O4–CuI are presented in Fig. 1. Characteristic
peaks of GO/Fe3O4–CuI are basically the same with GO and GO/
Fe3O4. The FTIR pattern of GO shows the presence of the oxygen-
containing functional groups. The peaks at 3370 cmÀ1, 1730 cmÀ1
are the results of the stretching of O–H, C55O in COOH. The band at
-1
Wavenumbers(cm)
Fig. 1. IR spectra of GO, GO/Fe3O4 and GO/Fe3O4–CuI.
1622 cmÀ1
, ,
1230 cmÀ1 and 1056 cmÀ1 can be assigned to
CuI
Fe3O4
aromatic C55C, carboxy C–O, and alkoxy C–O stretches [20],
respectively. The FTIR spectra of GO/Fe3O4–CuI and GO/Fe3O4 differ
from that of GO as evidenced by the new band at 580 cmÀ1
[21]. The peak at 1730 cmÀ1 disappeared in the FTIR pattern of GO/
Fe3O4–CuI and the new peaks that emerged from 800 cmÀ1 to
1000 cmÀ1 are attributed to the formation of –COOÀ after the
complex reaction with CuI.
Fig. 2 shows the XRD pattern of GO/Fe3O4–CuI. The main peaks
at 25.48, 41.68, and 49.28, marked by their indices (1 1 1), (2 2 0),
and (3 1 1) [22], show the characteristics of CuI on GO/
Fe3O4. Besides these, no significantly different peaks are observed
among the diffraction patterns of GO, GO/Fe3O4 and GO/Fe3O4–CuI,
which indicates that the CuI was finely attached on GO/Fe3O4.
GO/Fe3O4-CuI
CuI
Fe3O4
GO
10
20
30
40
50
60
70
80
2
θ (degree
)
Fig. 2. XRD patterns of GO, Fe3O4, CuI and GO/Fe3O4–CuI.
Please cite this article in press as: L.-L. Kong, L.-Y. Fan, Magnetically recyclable copper modified GO/Fe3O4 catalyst for efficient synthesis
of quinazolinones, Chin. Chem. Lett. (2016), http://dx.doi.org/10.1016/j.cclet.2016.01.055

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L.-L. Kong, L.-Y. Fan / Chinese Chemical Letters xxx (2016) xxx–xxx
3
Fig. 3. SEM images of GO/Fe3O4–CuI ((a) and (b)), GO/Fe3O4 (c) and GO (d).
Table 1
Table 3
Effect of different catalyst and base on the synthesis of 2-isopropylquinazolin-
4(3H)-one (3a)a.
Scope of 2-iodobenzamide and amino acid in synthesis of quinazolinone
derivativesa.
O
I
O
N
O
I
O
R1
R2
R1
R2
NH2 H2N
+
COOH
GO/Fe3O4-CuI
NH
NH2 H2N
+
COOH
NH
R3
Base, 120oC
DMSO/ethylene glycol,
R3
N
Catalyst,DMSO
Cs2CO3, 120 o
C
1a
2a
3a
3a-q
1a-c
2a-e
Entry
Catalyst
Base
Yield (%)d
Cu (mol%)
Entry 1
1
2
Product
Yield (%)b
72
1
/
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
Cs2CO3
Na2CO3
t-BuOK
Cs2CO3
Cs2CO3
0
/
2
CuBr
CuI
15
20
trace
trace
5
3.0
3.0
3.0
3.0
/
H2N
O
N
O
I
COOH
3
4
CuCl
CuCl2
GO
NH
NH2
5
2a
6
1a
7
GO/Fe3O4
GO/CuI
7
/
3a
8
25
27
30
15
0
42b
48b,c
3.0
3.0
3.0
3.0
3.0
3.0
3.0
9
GO/Fe3O4–CuI
GO/Fe3O4–CuI
GO/Fe3O4–CuI
GO/Fe3O4–CuI
GO/Fe3O4–CuI
GO/Fe3O4–CuI
2
3
4
1a
74
90
61
10
11
12
13
14
H2N
H2N
H2N
COOH
O
NH
NH
NH
2b
COOH
N
3b
a
2-Iodobenzamide 1a (1.0 equiv.), 2-aminoisovaleric acid 2a (2.0 equiv.), K2CO3
(2.0 equiv.), catalyst (Cu+ 0.03 equiv.), DMSO (3.0 mL), 120 8C.
1a
1a
O
b
Cs2CO3 (3.0 equiv.).
c
2-Aminoisovaleric acid 2a (3.0 equiv.).
d
Isolate yield.
N
2c
COOH
3c
O
Table 2
Optimization of solvent on the synthesis of 2-isopropylquinazolin-4(3H)-one (3a)
N
in the presence of GO/Fe3O4–CuI as catalysta.
2d
COOH
3d
O
O
I
O
N
5
6
1a
66
79
H2N
NH2 H2N
+
COOH
NH
GO/Fe3O4-CuI
NH
Solvent, Cs2CO3
reflux
N
1a
Entry
2a
3a
3e
O
2e
Solvent (v/v)
Yield (%)d
2a
O
1
DMSO
48
37
20
0
2
DMF
NH2
NH
3
NMP
4
ethylene glycol
F
I
F
N
1b
5
DMSO/ethanol (60:1)
DMSO/isopropanol (60:1)
DMSO/t-butanol (60:1)
DMSO/t-pentyl alcohol (60:1)
DMSO/ethylene glycol (60:1)
DMSO/ethylene glycol (50:1)
DMSO/ethylene glycol (70:1)
DMSO/ethylene glycol (60:1)
DMSO/ethylene glycol (60:1)
56
49
52
57
72
52
56
60b
62c
3f
6
7
7
8
1b
2b
2c
58
86
O
8
9
NH
NH
10
11
12
13
F
F
N
3g
1b
O
N
a
2-Iodobenzamide 1a (1.0 equiv.), 2-aminoisovaleric acid 2a (3.0 equiv.), Cs2CO3
(3.0 equiv.), catalyst (Cu+ 0.03 equiv.), solvent (3.0 mL).
b
Catalyst (Cu+ 0.024 equiv.).
Catalyst (Cu+ 0.039 equiv.).
c
3h
d
Isolate yield.
Please cite this article in press as: L.-L. Kong, L.-Y. Fan, Magnetically recyclable copper modified GO/Fe3O4 catalyst for efficient synthesis
of quinazolinones, Chin. Chem. Lett. (2016), http://dx.doi.org/10.1016/j.cclet.2016.01.055

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L.-L. Kong, L.-Y. Fan / Chinese Chemical Letters xxx (2016) xxx–xxx
Table 3 (Continued )
Table 4
Reuse the catalyst for the synthesis of 3aa.
Entry 1
2
Product
Yield (%)b
84
Entry
2-aminoisovalericacid (mmol)
Catalyst (mg)
Yield (%)b
9
1b
2d
O
N
Fresh
0.60
0.52
0.45
0.42
0.30
40
35
30
28
20
72
73
70
75
73
NH
NH
1st turn
2nd turn
3rd turn
4th turn
F
3i
O
a
2-Iodobenzamide 1a (1.0 equiv.), 2-aminoisovaleric acid 2a (3.0 equiv.), Cs2CO3
(3.0 equiv.), catalyst (Cu+ 0.03 equiv.), 3.0 mL DMSO/ethylene glycol (60:1, v/v),
120 8C.
10
2a
40
O
I
NH2
b
Isolate yield.
N
1c
3j
activity for the synthesis of 2-isopropylquinazolin-4(3H)-one (3a)
under the same reaction conditions, with the corresponding yields
not significantly reduced (Table 4).
128
129
130
11
12
13
1c
1c
1c
2b
2c
2d
53
49
49
O
NH
NH
NH
N
4. Conclusion
131
3k
O
In summary, we have successfully prepared the magnetically
recyclable heterogeneous catalyst GO/Fe3O4–CuI, which exhibited
high catalytic activity for the synthesis of quinazolinones
derivatives by the condensation of halide benzamide with amino
acid. Due to its unique planar structure, huge surface area,
magnetism, and chemicals features, the catalyst shows high
catalytic efficiency, magnetically recoverability, and reusability,
such that it can be used several times to give desired products
without any obvious loss of its catalytic activity. The magnetically
recyclable catalyst GO/Fe3O4–CuI shows its applicability as a
reusable and promising catalyst for quinazolinones synthesis.
132
133
134
135
136
137
138
139
140
141
142
N
3l
O
N
3m
14
2a
41
O
O
I
F
F
F
NH
NH
NH2
Acknowledgment
143
N
1d
This work was supported by the Research Foundation of Tongji Q2 144
University.
3n
Q3 145
15
16
17
1d
2c
2b
2c
43
58
69
O
Appendix A. Supplementary data
146
N
Supplementary data associated with this article can be found,
in the online version, at http://dx.doi.org/10.1016/j.cclet.2016.01.
055.
147
148
149
3o
O
O
N
NH
NH2
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150
Br
1e
3b
1e
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Please cite this article in press as: L.-L. Kong, L.-Y. Fan, Magnetically recyclable copper modified GO/Fe3O4 catalyst for efficient synthesis
of quinazolinones, Chin. Chem. Lett. (2016), http://dx.doi.org/10.1016/j.cclet.2016.01.055