Br?nsted acidic ionic liquids catalyze the preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives

Article abstract of DOI:10.1007/s11164-013-1071-x

A simple and facile method for the green synthesis of 2,3- dihydroquinazolin-4(1H)-one derivatives by direct three-component cyclo-condensation of isatoic anhydride, ammonium acetate (or primary amines), and arylaldehydes using different Br?nsted acidic ionic liquids, for example 2-pyrrolidonium hydrogensulfate ([hnmp][HSO₄]), N-methyl-2-pyrrolidonium hydrogensulfate ([NMP][HSO₄]), and N-methyl-2-pyrrolidonium dihydrogenphosphate ([NMP][H₂PO ₄]), as reusable catalysts under solvent-free conditions is described. In addition, reaction of anthranilamide and arylaldehydes for synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives was investigated.

Full text of DOI:10.1007/s11164-013-1071-x

Res Chem Intermed
DOI 10.1007/s11164-013-1071-x
Brønsted acidic ionic liquids catalyze the preparation
of 2,3-dihydroquinazolin-4(1H)-one derivatives
•
Hamid Reza Shaterian Morteza Aghakhanizadeh
Received: 20 November 2012 / Accepted: 23 January 2013
Ó Springer Science+Business Media Dordrecht 2013
Abstract A simple and facile method for the green synthesis of 2,3-dihydroqui-
nazolin-4(1H)-one derivatives by direct three-component cyclo-condensation of
isatoic anhydride, ammonium acetate (or primary amines), and arylaldehydes using
different Brønsted acidic ionic liquids, for example 2-pyrrolidonium hydrogensul-
fate ([hnmp][HSO4]), N-methyl-2-pyrrolidonium hydrogensulfate ([NMP][HSO4]),
and N-methyl-2-pyrrolidonium dihydrogenphosphate ([NMP][H2PO4]), as reus-
able catalysts under solvent-free conditions is described. In addition, reaction of
anthranilamide and arylaldehydes for synthesis of 2,3-dihydroquinazolin-4(1H)-one
derivatives was investigated.
Keywords 2,3-Hihydroquinazolin-4(1H)-one Á Anthranilamide Á Ionic liquid Á
Combinatorial chemistry Á Primary amine
Introduction
Multi-component reactions (MCRs) are important in combinatorial chemistry
because of the ability to synthesize target compounds with greater efficiency and
atom economy by generating structural complexity in a single step from three or
more reactants [1]. Moreover, MCRs have the advantage of simplicity and synthetic
efficiency over conventional chemical reactions [1].
Heterocyclic compounds are important because of their chemical, biological, and
technical significance [2]. Heterocyclic compounds include many natural products,
for example vitamins, hormones, antibiotics, alkaloids, pharmaceuticals, herbicides,
and dyes [3].
H. R. Shaterian (&) Á M. Aghakhanizadeh
Department of Chemistry, Faculty of Sciences, University of Sistan and Baluchestan,
PO Box 98135-674, Zahedan, Iran
e-mail: hrshaterian@chem.usb.ac.ir
123

H. R. Shaterian, M. Aghakhanizadeh
2,3-Dihydroquinazolinone derivatives have been reported to have a wide range of
pharmacological activity, for example anti-inflammatory and analgesic [4]. In
addition, these compounds as chemical intermediates can easily be oxidized to their
corresponding quinazolin-4(3H)-ones [5], which are also important biologically
active heterocyclic compounds [6]. Therefore, a variety of methods have been
developed for synthesis of quinazolinone structures, for example cyclization of o-
acylaminobenzamides [7], amidation of 2-aminobenzonitrile followed by oxidative
ring closure [8], and solid-phase synthesis of 2-arylamino-substituted quinazoli-
nones [9].
One of the most important aspects of green chemistry is the use of ionic liquids
(ILs) as more environmentally benign solvents and catalysts. ILs have several
advantages, for example control of product distribution, enhanced rate and/or
reactivity, ease of product recovery, catalyst immobilization, and reusability [10].
Quinazolinones have been prepared by three-component reaction of isatoic
anhydride, primary amine or ammonium acetate, and arylaldehydes in the presence of
several catalysts, for example aluminium methanesulfonate (Al(MS)3Á4H2O) [11],
p-toluenesulfonic acid (p-TSA) [12], KAl(SO4)2Á12H2O (alum) [13], 1-methyl-
imidazolium nitrate [Hmim][NO3] [14], silica supported ferric chloride (SiO2–FeCl3)
[15], silica-bonded N-propylsulfamic acid (SBNPSA) [16], acetic acid [17], copper
benzenesulfonate (Cu(C6H5SO3)2Á6H2O) [18], silica supported ferric chloride (SiO2–
FeCl3) [15], gallium(III) triflate (Ga(OTf)3) [19], and strontium chloride (SrCl2.6H2O)
[20]. They have also been prepared by condensation of anthranilamide and
arylaldehydes by using CuCl2, [21] 1-butyl-3-methylimidazolium hexafluorophos-
phate ([Bmim]PF6) [22], tetrabutylammonium bromide (Bu4NBr) [23], cerium(IV)
ammonium nitrate (CAN) [24], zirconium (IV) chloride (ZrCl4) [25], and H3PW12O40
[26], as catalysts. However, some of these procedures have limitations, for example
tedious process, long reaction times, high temperatures, harsh reaction conditions,
expensive reagents, and low yields. Thus, the development of novel methods for
synthesis of dihydroquinazolin-4(1H)-ones is of great importance because of the
potential biological and pharmaceutical activity of these compounds.
In continuation our research on new methods of organic synthesis [27–30], we
developed the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives by one-pot
three-component condensation of isatoic anhydride, ammonium acetate (or primary
amines), and arylaldehydes (Method A, Scheme 1) and by two-component reaction
of anthranilamide and arylaldehydes (Method B, Scheme 2), using three Brønsted
acidic ionic liquids (BAILs), 2-pyrrolidonium hydrogensulfate ([hnmp][HSO4]), N-
methyl-2-pyrrolidonium hydrogensulfate ([NMP][HSO4]), and N-methyl-2-pyrro-
lidonium dihydrogenphosphate ([NMP][H2PO4]) (Fig. 1), as catalysts.
Results and discussion
To achieve more efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones, reaction of
isatoic anhydride (1 mmol), ammonium acetate (1.2 mmol), and benzaldehyde
(1 mmol) was selected as model system, under thermal solvent-free conditions, to find
the optimum conditions. The preparation of 2-phenyl-2,3-dihydroquinazolin-4(1H)-
123

Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives
O
O
R2
R1
Ionic Liquids ( catalyst)
solvent free, 80oC
O
N
or
+ R1 CHO + R2 NH2
O
NH4OAc
N
N
H
H
Ionic Liquids: [hnmp][HSO4], [NMP][HSO4], and [NMP][H2PO4]
Scheme 1 Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives by three-component reaction of
isatoic anhydride, primary amine or ammonium acetate, and arylaldehydes
O
O
Ionic Liquids ( catalyst)
solvent free, 80oC
NH2
NH2
NH
R1
+ R1 CHO
N
H
Ionic Liquids: [hnmp][HSO4], [NMP][HSO4], and [NMP][H2PO4]
Scheme 2 Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives by condensation of anthra-
nilamide and arylaldehydes
O
O
O
H
H
H
HSO4
N
N
N
HSO4
H2PO4
CH3
CH3
H
[NMP][H2PO4]
[hnmp][HSO4]
[NMP][HSO4]
Fig. 1 The structures of [hnmp][HSO4], [NMP][HSO4], and [NMP][H2PO4]
one was studied at different reaction temperatures (25, 60, 80, 100, and 120 °C) and
with different amounts of acidic ionic liquids as catalyst (5, 10, 15, 20, 25, and
30 mol %) (Table 1). The best result was obtained by use of 5 mol % [hnmp][HSO4],
5 mol % [NMP][HSO4], or 5 mol % [NMP][H2PO4] at 80 °C (Table 1).
By use of these optimized reaction conditions, the condensation reaction of
isatoic anhydride, arylaldehydes and ammonium acetate as source of ammonia or
primary amines proceeded well and afforded the desired products (Table 2) in good
to excellent yields.
As shown in Table 2, arylaldehydes bearing either electron-donating or electron-
withdrawing groups on the aromatic ring were investigated. The substituent on the
phenyl ring did not make any difference in this reaction. We also used aliphatic
aldehydes, for example propionaldehyde and butyraldehyde instead of benzalde-
hydes. Experimental observation showed us that all the starting reactants were intact
after 12 h without formation of any by-products (Table 2, Entries 20, 21).
In continuation of our work, using these optimized reaction conditions, the scope
and efficiency of the reaction were investigated for the synthesis of 2,3-
dihydroquinazolin-4(1H)-one derivatives by direct condensation of arylaldehydes
(1 mmol), anthranilamide (1 mmol), with ILs (5 mol %) as catalysts under solvent-
free conditions (Table 3).
123

H. R. Shaterian, M. Aghakhanizadeh
Table 1 Optimization the amount of the acidic ionic liquids, 2-pyrrolidonium hydrogensulfate (IL1),
N-methyl-2-pyrrolidonium hydrogensulfate (IL2), and N-methyl-2-pyrrolidonium dihydrogenphosphate
(IL3), as catalysts at different temperature in the reaction of isatoic anhydride (1 mmol), ammonium
acetate (1.2 mmol), and benzaldehyde (1 mmol) under solvent-free conditions
Entry
Catalyst (mol %)
Temperature (°C)
Time (min)
Yield (%)a
IL1
IL2
IL3
IL1
IL2
IL3
1
2
–
5
100
100
100
100
100
100
100
25
180
9
180
8
180
9
22
91
93
92
88
78
80
–
28
89
87
90
90
75
82
–
19
87
90
88
85
80
75
–
3
10
15
20
25
30
5
10
11
11
25
30
180
45
11
9
9
11
13
14
19
23
180
50
13
9
4
10
10
17
21
180
43
10
8
5
6
7
8
9
5
60
57
89
91
90
60
87
89
92
70
85
87
90
10
11
12
a
5
80
5
100
120
5
7
6
8
Yields refer to isolated pure products
We also compared the results from preparation of 2,3-dihydroquinazolin-4(1H)-
one derivatives by direct condensation of isatoic anhydride, primary amines or
ammonium acetate, and arylaldehydes (Method A) and the reaction of anthranilamide
and arylaldehydes (Method B) using ILs as catalysts under solvent-free conditions.
Method A produces 2,3-dihydroquinazolin-4(1H)-ones in shorter reaction times and
higher yields than method B, because isatoic anhydride is more reactive than
anthranilamide. Loss of CO2 from isatoic anhydride is an excellent driving force for
the reaction and preparation of a more reactive intermediate for synthesis of 2,3-
dihydroquinazolin-4(1H)-ones in shorter reaction times and higher yields.
Next, we compared the results obtained by use of these ILs and other catalysts
reported in the literature for preparation of 2,3-dihydroquinazolin-4(1H)-ones, for
example Al(MS)3. 4H2O [11], p-TSA [12], KAl(SO4)2Á12H2O [13], Cu(C6H5SO3)2Á
6H2O,18 SiO2–FeCl [3, 15] Ga(OTf)[3, 19] SrCl2Á6H2O [20], CuCl [2, 21]
[Bmim]PF6, [22] Bu4NBr [23], ZrCl4, [25] and H3PW12O40 [26] (Table 4). Table 4
clearly reveals that 2-pyrrolidonium hydrogensulfate, N-methyl-2-pyrrolidonium
hydrogensulfate, and N-methyl-2-pyrrolidonium dihydrogenphosphate are effective
catalysts in terms of reaction time and yield of product obtained compared with
other reported catalysts.
On the basis of the literature [16] and our experimental results, a plausible
mechanism of the three-component reaction is proposed in Scheme 3. In the
presence of acidic ionic liquids as catalyst, first, the isatoic anhydride (1) is
activated, forming intermediate 2. The N-nucleophilic amine (3) then attacks on the
carbonyl unit of 2, producing intermediate 4, which in turn affords the intermediate
123

Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives
123

H. R. Shaterian, M. Aghakhanizadeh
123

Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives
123

H. R. Shaterian, M. Aghakhanizadeh
123

Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives
Table 3 Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives (Method B)
Entry
Aldehyde
Time (min)
Yield (%)a
M.p. (°C)
IL1
20
IL2
18
IL3
23
IL1
80
IL2
85
IL3
83
1
2
223–225
203–205
25
25
CHO
CHO
25
23
28
82
87
81
Cl
3
4
28
27
22
24
38
29
83
79
84
80
79
75
210–212
191–193
25
25
Cl
CHO
CHO
NO2
5
6
7
25
32
24
18
28
23
32
25
25
81
78
85
80
75
87
85
81
81
181–183
220
25
25
25
MeO
Me
CHO
CHO
CHO
199–201
O2N
8
9
a
720
720
720
720
720
720
–
–
–
–
–
–
–
–
–
–
CHO
CHO
Yields refer to isolated pure products
The molar ratio of the starting reactants was: arylaldehyde (1 mmol) and anthranilamide (1 mmol). The
reaction was performed in an oil bath at 80 °C
5 by decarboxylation and proton transfer. Subsequently, reaction of arylaldehyde
activated by ILs with 5 proceeds, resulting in formation of imine intermediate 7,
which cyclizes to yield the final product.
In green organic synthesis, recovery of catalysts is very important. Thus, the
reusability of ILs as catalysts was studied. After completion of the reaction, the
reaction mixture was cooled to room temperature and 5 mL water was added.
The ionic liquid dissolved in the water, and the solution was filtered to isolate the
crude product. The separated product was washed twice with water (2 9 5 mL). To
recover the ionic liquid, the water containing the IL was evaporated and the
remaining viscous liquid was washed with CH2Cl2 (5 mL) and dried under reduced
pressure. The recovered IL was tested to study its catalytic activity in the subsequent
123

H. R. Shaterian, M. Aghakhanizadeh
Table 4 Comparison of results obtained by use of 2-pyrrolidonium hydrogensulfate, N-methyl-2-pyr-
rolidonium hydrogensulfate, and N-methyl-2-pyrrolidonium dihydrogenphosphate with those obtained by
use of other catalysts reported in the literature for synthesis of 2,3-dihydroquinazolin-4(1H)-ones
Entry
Catalyst
Conditions
Time
(min)
Yield
(%)
Ref
1
Al(MS)3Á4H2O (5 mol %)a
p-TSA (50 mol %)a
p-TSA (50 mol %)a
KAl(SO4)2Á12H2O (40 mol %)a
Cu(C6H5SO3)2Á6H2O (40 mol %)a
SiO2–FeCl3 (0.005 g)a
Ga(OTf)3(1 mol %)a
EtOH/H2O, reflux
H2O, reflux
120
60
240
240
30
18
55
55
42
11
10
13
360
150
35
90
25
8
88
84
75
71
93
89
87
83
93
89
87
85
87
84
89
82
95
94
80
85
83
[11]
2
[12]
3
EtOH, reflux
[12]
4
EtOH, reflux
[13]
5
EtOH/H2O, reflux
Solvent-free, 80 °C
EtOH, 70 °C
[18]
6
[15]
7
[19]
8
Ga(OTf)3(1 mol %)a
DMSO, 85 °C
[19]
9
SrCl2.6H2O (1 mol %)a
[hnmp][HSO4] (5 mol %)a
[NMP][HSO4] (5 mol %)a
[NMP][H2PO4] (5 mol %)a
SiO2–FeCl3 (0.005 g)b
CuCl2 (100 mol %)b
[Bmim]PFb6
Bu4NBr (40 mol %)b
ZrCl4 (2 mol %)b
H3PW12O40 (0.1 mol %)b
[hnmp][HSO4] (5 mol %)b
[NMP][HSO4] (5 mol %)b
[NMP][H2PO4] (5 mol %)b
EtOH/H2O, reflux
Solvent-free, 80 °C
Solvent-free, 80 °C
Solvent-free, 80 °C
Solvent-free, 80 °C
EtOH, reflux,70 °C
75 °C
[20]
10
11
12
13
13
14
15
16
17
18
19
20
a
This work
This work
This work
[15]
[21]
[22]
N2 atmosphere, 100 °C
EtOH, r.t.
[23]
[25]
H2O, r.t.
[26]
Solvent-free, 80 °C
Solvent-free, 80 °C
Solvent-free, 80 °C
20
18
23
This work
This work
This work
Based on the reaction of isatoic anhydride, ammonium acetate, and benzaldehyde
b
Based on the reaction of anthranilamide and benzaldehyde
run without addition of fresh catalyst. ILs were tested for five runs. It was observed
that the ILs as catalysts had very good reusability without substantial loss of their
activity (Fig. 2).
In conclusion, we have described a rapid and highly efficient method for the
green synthesis of 2,3-dihydroquinazolin-4(1H)-ones by direct one-pot, three-
component reaction of isatoic anhydride, ammonium acetate (or primary amines)
and arylaldehydes (Method A) or anthranilamide and arylaldehydes (Method B)
using Brønsted reusable acidic ionic liquids as catalysts under thermal solvent-free
reaction conditions. With such successful results, this convenient and efficient
procedure should provide a superior alternative to the existing methods because of
its rapid and clean reactions and high yields. Furthermore, the simple work-up
procedure makes these methods useful and important for synthesis of 2,3-
dihydroquinazolin-4(1H)-ones.
123

Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives
O
(3)
H
N
R2 NH2
H
R2
O
NH
OH
OH
O
CO2
R2
(4)
N
H
O
(2)
O
O
N
O
H
NH2
N
H
O
(5)
(1)
O
HSO4
H
N
R1 CHO
(6)
H
O
HSO4
H
H
N
O
H
O
N
H
(7)
R2
N R2
R1
N
N
H
R1
product
Scheme 3 The catalytic mechanism for preparation of the 2,3-dihydroquinazolin-4(1H)-one derivatives,
with 2-pyrrolidonium hydrogensulfate as selected ionic liquid
Experimental
General
All reagents were purchased from Merck and Sigma–Aldrich and used without
further purification. Ionic liquids, 2-pyrrolidonium hydrogensulfate ([hnmp][HSO4])
Fig. 2 Reusability of ionic liquids as catalysts
123

H. R. Shaterian, M. Aghakhanizadeh
[31], N-methyl-2-pyrrolidonium hydrogensulfate ([NMP][HSO4]) [32], and N-
methyl-2-pyrrolidonium dihydrogenphosphate ([NMP][H2PO4]) [33], were pre-
pared in accordance with reported procedures. All yields refer to isolated products
after purification. NMR spectra were recorded on a Bruker Avance DPX 500 MHz
instrument, in DMSO-d6 as solvent, relative to TMS (0.00 ppm). IR spectra were
recorded on a Jasco FT-IR 460 plus spectrophotometer. Melting points were
determined in open capillaries with a Buchi 510 melting point apparatus. TLC was
performed on Polygram SILG/UV 254 silica gel plates.
General procedure for synthesis of 2,3-dihydroquinazolin-4(1H)-ones by three-
component reaction of isatoic anhydride, primary amine or ammonium acetate,
and arylaldehydes (Method A)
A stirred mixture of isatoic anhydride (10 mmol), ammonium acetate (or primary
amine) (12 mmol), arylaldehyde (10 mmol), and 2-pyrrolidonium hydrogensulfate
(0.09 g, 5 mol %, 0.5 mmol) or N-methyl-2-pyrrolidonium hydrogensulfate
(0.098 g, 5 mol %, 0.5 mmol) or N-methyl-2-pyrrolidonium dihydrogenphosphate
(0.098 g, 5 mol %, 0.5 mmol) was reacted in an oil bath at 80 °C for the
appropriate time (Table 2). After completion of the reaction (indicated by TLC)
the mixture was cooled to room temperature and 5 mL water was added. The
ionic liquid dissolved in the water, and the mixture was filtered for separation of
the crude product. The separated product was washed twice with water
(2 9 5 mL) then purified by recrystallization from ethanol. To recover the ionic
liquids, after isolation of the insoluble products, the water was evaporated and the
remaining viscous liquid was washed with CH2Cl2 (5 mL) and dried under
reduced pressure.
General procedure for synthesis of 2,3-dihydroquinazolin-4(1H)-ones
by reaction of anthranilamide and arylaldehydes (Method B)
A mixture of arylaldehyde (10 mmol), anthranilamide (10 mmol), and 2-pyrrolid-
onium hydrogensulfate (0.09 g, 5 mol %, 0.05 mmol) or N-methyl-2-pyrrolidoni-
um hydrogensulfate (0.098 g, 5 mol %, 0.5 mmol) or N-methyl-2-pyrrolidonium
dihydrogenphosphate (0.098 g, 5 mol %, 0.5 mmol) was reacted in an oil bath at
80 °C for the appropriate time (Table 3). After completion of the reaction
(indicated by TLC) the mixture was cooled to room temperature and 5 mL water
was added. The ionic liquid dissolved in the water, and the mixture was filtered for
separation of the crude product. The separated product was washed twice with
water (2 9 5 mL) then purified by recrystallization from ethanol. To recover the
ionic liquids, after isolation of the insoluble products, water was evaporated and
the remaining viscous liquid was washed with CH2Cl2 (5 mL) and dried under
reduced pressure.
All the products are known. NMR and IR spectroscopic data for two of the
compounds are given below.
123

Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives
2-(2-Chlorophenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one (Table 2, Entry 17)
1
M.p. 138–140 °C; H NMR (500 MHz, DMSO-d6): d = 6.60 (d, J = 2.7 Hz, 1H),
6.74–6.79 (m, 2H), 7.17–7.21 (m, 3H), 7.27–7.31 (m, 5H), 7.37–7.39 (m, 1H), 7.46
(d, J = 2.5 Hz, 1H), 7.58–7.60 (m, 1H), 7.77 (dd, J = 1.3, 6.4 Hz, 1H), ppm; 13C
NMR (125 MHz, DMSO-d6): d = 70.2, 114.6, 114.8, 117.6, 126.6, 126.9, 127.4,
127.8, 128.2, 128.6, 129.8, 130.3, 131.3, 133.8, 136.9, 140.1, 146.0, 162.2 ppm; IR
(KBr, cm-1): 758, 1452, 1491, 1606, 1637, 2361, 3070, 3309.
2-(4-Nitrophenyl)-2,3-dihydroquinazolin-4(1H)-one (Table 3, Entry 7)
1
M.p. 199–201 °C; H NMR (500 MHz, DMSO-d6): d = 5.93 (1H, s, CH), 6.71
(1H, t, J = 7.4, H Ar), 6.79 (1H, d, J = 8.1, H Ar), 7.29 (1H, t, J = 7.4, H Ar), 7.33
(1H, s, NH), 7.64 (1H, d, J = 7.6, H Ar), 7.76 (2H, d, J = 8.6, H Ar), 8.27 (2H, d,
J = 8.6, H Ar), 8.53 (1H, s, CONH) ppm; 13C NMR (125 MHz, DMSO-d6):
d = 65.2, 114.5, 114.8, 117.4, 123.5, 127.3, 127.9, 133.4, 147.2, 147.4, 149.2,
163.2 ppm; IR (KBr, cm-1): 753, 859, 1012, 1162, 1348, 1486, 1521, 1613, 1661,
3291, 3363.
Acknowledgments We are grateful to the University of Sistan and Baluchestan Research Council for
the partial support of this research.
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