Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)- ones using aluminum methanesulfonate as a reusable catalyst

Article abstract of DOI:10.1007/s11164-011-0445-1

A wide range of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones were synthesized via a one-pot three components condensation of isatoic anhydride, aldehydes, and ammonium salts or primary amines in the presence of aluminum methanesulfonate in EtOH/H₂O solution. The catalyst is reusable and could be recycled for several runs without any distinct decrease in its efficiency. A plausible mechanism for this one-pot three components reaction was proposed. Springer Science+Business Media B.V. 2011.

Full text of DOI:10.1007/s11164-011-0445-1

Res Chem Intermed (2012) 38:1091–1099
DOI 10.1007/s11164-011-0445-1
Efficient synthesis of mono- and disubstituted
2,3-dihydroquinazolin-4(1H)-ones using aluminum
methanesulfonate as a reusable catalyst
•
Zhiguo Song Lianli Liu Yang Wang Xiaohu Sun
•
•
Received: 18 October 2011 / Accepted: 18 November 2011 / Published online: 1 December 2011
Ó Springer Science+Business Media B.V. 2011
Abstract A wide range of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-
ones were synthesized via a one-pot three components condensation of isatoic
anhydride, aldehydes, and ammonium salts or primary amines in the presence of
aluminum methanesulfonate in EtOH/H2O solution. The catalyst is reusable and
could be recycled for several runs without any distinct decrease in its efficiency.
A plausible mechanism for this one-pot three components reaction was proposed.
Keywords 2,3-Dihydroquinazolin-4(1H)-ones Á Aluminum methanesulfonate Á
Multicomponent reactions Á Isatoic anhydride
Introduction
2,3-Dihydroquinazolinone derivatives have been reported to possess a wide range
of pharmacological activities such as anti-inflammatory and analgesic activities [1],
and antitumor [2], anticancer [3], antibacterial [4], and diuretic activities [5]. In
addition, these compounds as chemical intermediates can easily be oxidized to their
corresponding quinazolin-4(3H)-ones [6], which are also important biologically
active heterocyclic compounds [7, 8].
Several methods have been reported for the synthesis of 2,3-dihydroquinazoli-
nones. Among them, the most direct procedure includes condensation of the
appropriate derivatives of anthranilamide with an aldehyde or ketone in the presence
of Brønsted acid or Lewis acid [9–15]. However, these methods suffer from low
Z. Song (&) Á L. Liu Á Y. Wang Á X. Sun
Center for Science & Technology Experiment, Bohai University, Jinzhou 121000,
People’s Republic of China
e-mail: lnszgsky@yahoo.com.cn
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Z. Song et al.
yields and/or vigorous conditions. The structures of products are limited. Other
synthetic methods for access to this bicyclic system are not general in scope
[16, 17]. Therefore, simple, efficient and environmentally benign procedures for
synthesizing 2,3-dihydroquinazolin-4(1H)-ones are still in demand.
One-pot multi-component reactions (MCRs) are very important and attractive
subjects in organic synthesis due to the formation of carbon–carbon and carbon–
hetero atom bonds. They are performed without needing to isolate any intermediate
during their process, which saves time, energy and raw materials. Very recently,
Dabiri and Salehi first reported that 2,3-dihydroquinazolin-4(1H)-ones could be
synthesized from a novel one-pot three components condensation of isatoic
anhydride, an aromatic aldehyde, and a primary amine or ammonium salts [18, 19].
Since then, some other catalysts such as p-TsOH [20], acetic acid [21], Zn(PFO)2
[22], Ga(OTf)3 [23], ionic liquid [24, 25], montmorillonite K-10 [26, 27],
Al(H2PO4)3 [28], I2 [29, 30], amberlyst-15 [31], silica sulfuric acid [32],
silica-bonded S-sulfonic acid [33], Al/Al2O3 and Fe3O4 nanoparticles [34, 35],
copolymer-PTSA [36], MCM-41-SO3H [37], SiO2–FeCl3 [38] and silica-bonded
N-propylsulfamic acid [39] have also been reported. However, these methodol-
ogies suffer from at least one of the following disadvantages: long reaction time,
high temperature, and costly reagents. Now, during our continuous study on
green and efficient MCRs, we report here a one-pot three components synthesis
of 2,3-dihydroquinazolin-4(1H)-ones from isatoic anhydride, aldehydes, and
ammonium salts or primary amines in the presence of 5 mol% (based on
aldehyde) aluminum methanesulfonate (Al(MS)3Á4H2O) in EtOH/H2O solution
(Scheme 1). Metal methanesulfonates (M(MS)xÁaH2O) as water-tolerant Lewis
acid catalysts have been well documented in recent years [40–45]. The new
synthetic protocol enlarges the application scope of metal methanesulfonates in
organic synthesis.
O
O
(NH4)2CO3
or
O
Al(MS)3 4H2O (5 mol%)
EtOH/H2O (1/1)
NH
+
+
R1CHO
NH4OAc
N
H
O
N
H
R1
1
2
3a-3j
O
O
R2
O
Al(MS)3 4H2O (5 mol%)
EtOH/H2O (1/1)
N
+
+
R1CHO
R2NH2
N
H
O
N
H
R1
1
4
5
6a-6r
Scheme 1 Al(MS)3Á4H2O-catalyzed synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-
ones in ethanol aqueous solution
123

Synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones
1093
Experimental
General
Melting points were determined using a RD-II micromelting point apparatus.
Infrared spectra were recorded on a Scimitar 2000 series Fourier Transform
instrument of VARIAN (KBr diluted pellets). 1H NMR and 13C NMR spectra were
recorded on a Bruker ARX-500 spectrometer in DMSO-d6 using TMS as an internal
standard. Mass spectra were obtained with an Agilent 1100 series LC/MSD VL ESI
instrument. Elemental analyses were carried out on an EA 2400II elemental
analyzer (PerkinElmer).
Synthesis and characterization of M(MS)xÁaH2O
M(MS)xÁaH2O were synthesized according to Ref. [41]. They were characterized by
IR and Thermogravimetry (TG) analysis. Taking Al(MS)3Á4H2O as an example, IR
data: mas (SO3) 1,189 cm-1, ms (SO3) 1,061 cm-1, mas (CH3) 2,941 cm-1, ds (CH3)
1,384 cm-1. TG curves were monitored on a Perkin-Elmer Pyris 1 TGA (sample
mass is about 2.5 mg). Experiments were conducted in dynamic Air atmosphere
(20 mL/min) at a heating rate of 20 °C min-1 from 30 to 850 °C. Crystal water’s
weight losing ratio is 17.9%, number of crystal water is 4, starting decomposition
temperature is 200 °C, and weight content of pyrolytic product is 13.2%.
General procedure for preparation of 2,3-dihydroquinazolin-4(1H)-ones
catalyzed by Al(MS)3Á4H2O
A stirred mixture of isatoic anhydride (0.915 g, 5.5 mmol), aldehyde (5 mmol),
ammonium salt or primary amine (5.5 mmol) and Al(MS)3Á4H2O (0.096 g,
0.25 mmol) in 5 mL EtOH/H2O (1/1 (v/v)) was refluxed for an appropriate time
as indicated in Tables 3 and 4. When the reaction completed as monitored by TLC,
the reaction mixture was cooled to room temperature. The corresponding pure
product was obtained by simple filtering, washed with 3 9 10 mL 50% ethanol
aqueous solution for three times, and recrystallized from EtOH. The filtrate
containing the catalyst was evaporated under reduced pressure to give the recovered
catalyst, which could be reused without further treatment. The products were
1
characterized by IR, H NMR, LC/MS, and elemental analysis. Spectral data for
some new compounds:
2,3-Dihydro-2-(2-chlorophenyl)-3-phenyl-quinazolin-4(1H)-one (6c): white
1
crystal, IR (KBr): 3,309, 3,070, 2,361, 1,637, 1,606, 1,491, 1,452, 758 cm-1; H
NMR (500 MHz, DMSO-d6): d 7.77 (dd, J = 1.3, 6.4 Hz, 1H), 7.60–7.58 (m, 1H),
7.46 (d, J = 2.5 Hz, 1H), 7.39–7.37 (m, 1H), 7.31–7.27 (m, 5H), 7.21–7.17 (m,
3H), 6.79–6.74 (m, 2H), 6.60 (d, J = 2.7 Hz, 1H); 13C NMR (125 MHz, DMSO-
d6): d 162.2, 146.0, 140.1, 136.9, 133.8, 131.3, 130.3, 129.8, 128.6, 128.2, 127.8,
127.4, 126.9, 126.6, 117.6, 114.8, 114.6, 70.2; MS (ESI): m/z (%) 335 (M ? H?,
100), 336 (23), 337 (36), 338 (8), 315 (6); Anal. Calcd. for C20H15N2OCl: C, 71.74;
H, 4.52; N, 8.37. Found: C, 71.59; H, 4.61; N, 8.46.
123

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Z. Song et al.
2,3-Dihydro-2-(4-nitrophenyl)-3-methyl-quinazolin-4(1H)-one (6k): yellow
crystal, IR (KBr): 3,309, 2,360, 1,644, 1,599, 1,521, 1,457, 1,407, 763 cm-1
;
1H NMR (500 MHz, DMSO-d6): d 8.74 (s, 1H), 8.37 (d, J = 8.5 Hz, 3H), 8.20
(d, J = 8.6 Hz, 2H), 7.76 (d, J = 6.9 Hz, 1H), 7.53 (t, J = 6.9 Hz, 1H), 7.35
(t, J = 7.4 Hz, 1H), 7.27 (d, J = 7.8 Hz, 1H), 2.80 (d, J = 4.6 Hz, 3H); 13C NMR
(125 MHz, DMSO-d6): d 160.2, 149.0, 148.2, 141.1, 131.2, 129.9, 129.7, 129.2,
126.5, 124.0, 119.0, 70.1, 26.1; MS (ESI): m/z (%) 284 (M ? H?, 100), 282 (22);
Anal. Calcd. for C15H13N3O3: C, 63.60; H, 4.62; N, 14.83. Found: C, 63.78; H, 4.70;
N, 14.69.
2,3-Dihydro-2-phenyl-3-n-propyl-quinazolin-4(1H)-one (6p): white crystal, IR
(KBr): 3,303, 3,065, 2,361, 1,630, 1,588, 1,507, 1,458, 748 cm-1 1H NMR
;
(500 MHz, DMSO-d6): d 7.65 (dd, J = 1.2, 6.5 Hz, 1H), 7.34–7.27 (m, 6H), 7.18
(dt, J = 1.5, 6.8 Hz, 1H), 6.66–6.62 (m, 2H), 5.83 (d, J = 2.5 Hz, 1H), 3.86–3.81
(m, 1H), 2.75–2.69 (m, 1H), 1.63–1.41 (m, 2H), 0.82 (t, J = 7.4 Hz, 3H); 13C NMR
(125 MHz, DMSO-d6): d 162.1, 146.2, 141.2, 133.0, 128.4, 128.2, 127.3, 126.0,
117.0, 115.0, 114.2, 70.1, 46.0, 20.7, 11.1; MS (ESI): m/z (%) 267 (M ? H?, 100),
268 (19); Anal. Calcd. for C17H18N2O: C, 76.66; H, 6.82; N, 10.52. Found: C,
76.81; H, 6.74; N, 10.41.
2,3-Dihydro-2-phenyl-3-benzyl-quinazolin-4(1H)-one (6r): white crystal, IR
(KBr): 3,401, 3,023, 2,361, 1,633, 1,579, 1,502, 1,447, 749 cm-1 1H NMR
;
(500 MHz, DMSO-d6): d 7.70 (dd, J = 1.4, 6.4 Hz, 1H), 7.36–7.20 (m, 12H),
6.69–6.63 (m, 2H), 5.74 (d, J = 2.6 Hz, 1H), 5.34 (d, J = 15.4 Hz, 1H), 3.83
(d, J = 15.4 Hz, 1H); 13C NMR (125 MHz, DMSO-d6): d 162.3, 146.2, 140.5,
137.4, 133.3, 128.5, 128.4, 127.6, 127.4, 127.1, 126.1, 117.2, 114.6, 114.3, 69.8,
47.1; MS (ESI): m/z (%) 315 (M ? H?, 100), 316 (24); Anal. Calcd. for
C21H18N2O: C, 80.22; H, 5.78; N, 8.91. Found: C, 80.39; H, 5.67; N, 8.99.
Results and discussion
At the outset, we investigated the catalytic activity of different M(MS)xÁaH2O
(0.25 mmol) using the model reaction of isatoic anhydride (5.5 mmol), benzalde-
hyde (5 mmol) and ammonium acetate (5.5 mmol) in EtOH (5 mL) under reflux
with vigorous stirring for 2 h. The results are summarized in Table 1. After several
trials, it was found that the catalytic activity of Al(MS)3Á4H2O was similar to that of
transition metal methanesulfonates, rare earth metal methanesulfonates, alkaline
earth metal methanesulfonates, and alkali metal methanesulfonate. They all gave
good yields, which were above 70%. We chose Al(MS)3Á4H2O as the most
promising catalyst because it is economical and it gave a higher yield. When no
catalyst was used, a low yield of the product was produced (Table 1, entry 18).
Next, we examined the above reaction in different solvents under reflux for 2 h
(Table 2). Only H2O and EtOH, the clean solvent and relatively benign organic
solvent, were investigated to standardize the reaction condition (Table 2, entries
1–5). It seems that EtOH/H2O (1/1 (v/v)) system is the best for the catalytic
reactions in terms of yield, environmental protection, and product isolation
(Table 2, entry 4).
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Synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones
1095
Table 1 Catalytic activity of M(MS)xÁaH2O in the reaction of isatoic anhydride, benzaldehyde, and
ammonium acetate
O
O
O
M(MS)x aH2O
NH
NH4OAc
+
+
PhCHO
EtOH, reflux
N
H
O
N
H
Ph
Entry
M(MS)xÁaH2O
Yield (%)
1
Al(MS)3Á4H2O
Fe(MS)2Á4H2O
Cu(MS)2Á4H2O
Cd(MS)2Á2H2O
Zn(MS)2Á4H2O
Mn(MS)2Á2H2O
Ni(MS)2Á4H2O
Ce(MS)3Á2H2O
La(MS)3Á2H2O
Pr(MS)3Á2H2O
Yb(MS)3Á3H2O
Nd(MS)3Á2H2O
Sr(MS)2Á3H2O
Ba(MS)2
88
87
85
80
80
79
70
83
82
80
76
71
81
78
76
74
81
39
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
Ca(MS)2
Mg(MS)2Á2H2O
Li(MS)Á2H2O
None
After reaction, the resulted mixture was washed with ethanol aqueous solution.
The catalyst remaining in the aqueous phase could be recovered by evaporating the
filtrate. Al(MS)3Á4H2O could be reused several times without further treatment. In
order to demonstrate the water-tolerant ability of Al(MS)3Á4H2O, the recovered
catalyst was washed with acetone and tested by IR and TG. The results showed that
the spectra data of the recovered catalyst were nearly consistent with that of the
fresh catalyst. The results are indicated in Table 2, entry 4. In this case, no distinct
loss of activity was observed after four successive runs.
The optimal amount of solvent was also investigated (Table 2, entries 4, 6 and 7).
The results show 5 mL EtOH/H2O (1/1; v/v) was suitable to facilitate the reaction.
Further studies showed that the amount of Al(MS)3Á4H2O affected the reaction
significantly (Table 2, entries 4, 8–10). The product yields enhanced along with the
increase in the amount of catalyst. A satisfactory yield was achieved in the presence
of 5 mol% Al(MS)3Á4H2O, while 10 mol% catalyst did not bring an obviously
better yield.
123

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Z. Song et al.
Table 2 Condensation of isatoic anhydride, benzaldehyde, and ammonium acetate under various reac-
tion conditions
O
O
Al(MS)3 4H2O
O
NH
+
+
NH4OAc
PhCHO
N
H
O
N
H
Ph
Entry
Solvent (mL)
Amount of catalyst (mol%)
Yield (%)
1
2
3
4
5
6
7
8
9
10
a
None
5
5
74a
65
H2O (5.0)
EtOH (5.0)
5
88
88, 86, 84, 81b
EtOH (2.5) ? H2O (2.5)
EtOH (1.5) ? H2O (3.5)
EtOH (1.5) ? H2O (1.5)
EtOH (4.0) ? H2O (4.0)
EtOH (2.5) ? H2O (2.5)
EtOH (2.5) ? H2O (2.5)
EtOH (2.5) ? H2O (2.5)
5
5
83
83
72
73
80
89
5
5
1
3
10
Yield refers to without solvent at 80 °C
Catalyst was reused four times
b
With the optimized conditions in hand, we explored the scope of the one-pot
three components cyclocondensation reaction. Ammonium carbonate and ammo-
nium acetate were employed as the source of ammonia, which was mixed with
isatoic anhydride and aldehydes in the presence of Al(MS)3Á4H2O to give the
corresponding 2-substituted-2,3-dihydroquinazolin-4(1H)-ones under the conditions
(Table 3). Whether the aromatic ring was bearing electron-withdrawing or electron-
donating groups, the corresponding 2-aryl-2,3-dihydroquinazolin-4(1H)-ones deriv-
atives were obtained in good yields. However, no desired products were produced
when NH4Cl was used. In the case of aliphatic aldehyde such as propionaldehyde, a
trace of product was yielded under these conditions (Table 3, entry 10).
On the other hand, we investigated the synthesis of 2,3-disubstituted-2,3-
dihydroquinazolin-4(1H)-ones from isatoic anhydride, aldehydes and primary
amines under the optimized conditions (Table 4). All the reactions proceeded
smoothly. Aromatic aldehydes carrying either electron-withdrawing or electron-
donating groups afforded the desired products in moderate to high yields. However,
only trace products were isolated when propionaldehyde and cinnamaldehyde were
used (Table 4, entries 6 and 7). Aromatic and aliphatic amines worked well under
the reaction conditions.
A plausible mechanism for this one-pot three components reaction was proposed.
The first step may involve the condensation of isatoic anhydride activated by
Al(MS)3Á4H2O with ammonium salts/primary amine, then followed by decarbox-
ylation to yield the corresponding 2-aminobenzamide. Next step, imine intermediate
123

Synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones
1097
Table 3 Al(MS)3Á4H2O-catalyzed synthesis of 2-substituted-2,3-dihydroquinazolin-4(1H)-ones by the
reaction of isatoic anhydride, aldehydes, and ammonium salts
O
O
(NH4)2CO3
or
O
Al(MS)3 4H2O (5 mol%)
EtOH/H2O (1/1)
NH
+
+
R1CHO
NH4OAc
N
H
O
N
H
R1
1
2
3a-3j
Entry R1
Ammonium salt Time (h) Product Yield (%) Mp (°C)
Found
Lit.
1
C6H5
(NH4)2CO3
(NH4)2CO3
(NH4)2CO3
(NH4)2CO3
(NH4)2CO3
(NH4)2CO3
(NH4)2CO3
(NH4)2CO3
1.0
1.0
4.5
0.5
0.5
3.0
1.0
1.0
1.0
4.0
2.0
5.0
6.5
2.0
1.0
6.0
1.0
1.0
1.5
3a
3b
3c
3d
3e
3f
91
93
94
90
88
95
82
91
80
Trace
88
93
95
96
80
92
60
80
90
224–226 218–220 [26]
190–192 190–192 [46]
198–200 198–200 [46]
203–205 203–205 [46]
210–211 205–206 [23]
165–167 167–169 [46]
221–222 225–227 [10]
182–184 178–180 [26]
208–210 206–208 [46]
2
3-O2NC6H4
4-O2NC6H4
2-ClC6H4
3
4
5
4-ClC6H4
6
2,4-Cl2C6H3
4-MeC6H4
4-MeOC6H4
7
3g
3h
3i
8
9
4-(Me)2NC6H4 (NH4)2CO3
10
11
12
13
14
15
16
17
18
19
CH3CH2
(NH4)2CO3
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
NH4OAc
3j
–
–
C6H5
3a
3b
3c
3d
3e
3f
224–226 218–220 [26]
190–192 190–192 [46]
198–200 198–200 [46]
202–203 203–205 [46]
210–211 205–206 [23]
165–167 167–169 [46]
221–222 225–227 [10]
182–184 178–180 [26]
206–208 206–208 [46]
3-O2NC6H4
4-O2NC6H4
2-ClC6H4
4-ClC6H4
2,4-Cl2C6H3
4-MeC6H4
4-MeOC6H4
3g
3h
3i
4-(Me)2NC6H4 NH4OAc
Reaction conditions: isatoic anhydride (5.5 mmol), aromatic aldehydes (5 mmol), ammonium salts
(5.5 mmol), Al(MS)3Á4H2O (5 mol%), EtOH/H2O (5 mL, 1/1; v/v), under reflux
could be obtained by addition of 2-aminobenzamide with aldehydes promoted by
Al(MS)3Á4H2O. Subsequently, imine intermediate undergoes cyclization to afford
the 2,3-dihydroquinazolin-4(1H)-ones. Similar mechanisms of this reaction have
been reported and supported before by Dabiri et al. [18] and Wang et al. [22].
Conclusions
In conclusion, we have described an efficient strategy for the synthesis of mono- and
disubstituted 2,3-dihydroquinazolin-4(1H)-ones via a one-pot three components
123

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Z. Song et al.
Table 4 Al(MS)3Á4H2O-catalyzed synthesis of 2,3-disubstituted-2,3-dihydroquinazolin-4(1H)-ones by
the reaction of isatoic anhydride, aldehydes, and primary amines
O
O
R2
O
Al(MS)3 4H2O (5 mol%)
EtOH/H2O (1/1)
N
+
+
R1CHO
R2NH2
N
H
O
N
H
R1
1
4
5
6a-6r
Entry R1
R2
Time (h) Product Yield (%) Mp (°C)
Found
Reported
1
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
C6H5
1.5
6.0
4.0
2.0
1.5
6.0
6.0
1.5
6a
6b
6c
6d
6e
6f
90
216–217 214–215 [23]
185–186 186–188 [26]
2
3-O2NC6H4
2-ClC6H4
4-ClC6H4
4-MeOC6H4
CH3CH2
95
3
93
211–212
–
4
74
223–225 219–220 [23]
203–204 204–205 [22]
5
82
6
Trace
Trace
60
–
–
–
–
7
C6H5CH=CH C6H5
6g
6h
6i
8
C6H5
4-ClC6H4
208–209 210–212 [22]
196–197 196–199 [22]
159–160 165 [26]
9
C6H5
4-CH3C6H4 1.5
76
10
11
12
13
14
15
16
17
18
C6H5
Me
7.0
1.0
7.0
6.0
2.0
6.0
6.5
5.0
6.0
6j
54
4-O2NC6H4
4-ClC6H4
C6H5
Me
6k
6l
87
200–202
–
Me
33
190–191 190 [26]
Et
6m
6n
6o
6p
6q
6r
85
130–131 134–137 [26]
170–171 176–178 [26]
130–132 132–135 [26]
3-O2NC6H4
4-ClC6H4
C6H5
Et
73
Et
34
n-Pr
n-Bu
C6H5CH2
51
120–121
127–128 120–122 [22]
158–159
–
C6H5
92
C6H5
88
–
Reaction conditions: isatoic anhydride (5.5 mmol), aldehydes (5 mmol), amines (5.5 mmol),
Al(MS)3Á4H2O (5 mol%), EtOH/H2O (5 mL, 1/1; v/v), under reflux
condensation of isatoic anhydride, aldehydes, and ammonium salts or primary
amines using the inexpensive, water-tolerant, and recyclable Al(MS)3Á4H2O as a
catalyst in EtOH/H2O solution. The method offers several advantages including
mild reaction conditions, simple work-up, easy recovery and reusable catalyst, and
extensive application scope. Furthermore, the novel catalyst is expected to
contribute the development of a more benign reaction in water or aqueous media,
and the related work is underway in our laboratory.
Acknowledgment This research work was financially supported by the Committee of Science and
Technology of Liaoning Province of China (No. 20091001).
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Synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones
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