Green protocol for synthesis of 2,3-dihydroquinazolin-4(1H)-ones: lactic acid as catalyst under solvent-free condition

Article abstract of DOI:10.1007/s11164-016-2469-z

Abstract: In the present work, lactic acid was used as novel, green catalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives via two distinct methods, including reaction of 2-aminobenzamide with aldehydes/ketones or isatoic anhydride with ammonium acetate and aldehydes in neat condition at 70?°C. The desired products were obtained in satisfactory yields. Short reaction time, easy workup, and more importantly environmental benignity are the most outstanding advantages of these procedures. Graphical Abstract: [Figure not available: see fulltext.]

Full text of DOI:10.1007/s11164-016-2469-z

Res Chem Intermed
DOI 10.1007/s11164-016-2469-z
Green protocol for synthesis of 2,3-dihydroquinazolin-
4(1H)-ones: lactic acid as catalyst under solvent-free
condition
Sara Zhaleh1 Nourallah Hazeri1 Malek Taher Maghsoodlou1
•
•
Received: 17 December 2015 / Accepted: 30 January 2016
Ó Springer Science+Business Media Dordrecht 2016
Abstract In the present work, lactic acid was used as novel, green catalyst for syn-
thesis of 2,3-dihydroquinazolin-4(1H)-one derivatives via two distinct methods,
including reaction of 2-aminobenzamide with aldehydes/ketones or isatoic anhydride
with ammonium acetate and aldehydes in neat condition at 70 °C. The desired products
were obtained in satisfactory yields. Short reaction time, easy workup, and more
importantly environmental benignity are the most outstanding advantages of these
procedures.
Graphical Abstract
O
R1
R2
O
+
NH2
NH2
20 mol% lactic acid
O
NH
R2
R1
N
H
O
+
R1
R2
O
solvent-free
O
70°
C
N
H
O
+
NH4OAC
Electronic supplementary material The online version of this article (doi:10.1007/s11164-016-2469-z)
contains supplementary material, which is available to authorized users.
&
Nourallah Hazeri
nhazeri@chem.usb.ac.ir
1
Department of Chemistry, University of Sistan and Baluchestan,
P. O. Box 98135-674, Zahedan, Iran
123

S. Zhaleh et al.
Keywords Green synthesis Á Lactic acid Á 2,3-Dihydroquinazolin-4(1H)-one Á
Solvent-free
Introduction
Synthesis of biologically and pharmacologically active organic compounds has
drawn much attention in recent years; among them, nitrogen-containing hetero-
cyclic compounds are of importance due to their applications in many biological
processes as markers or messenger molecules and also their use as agrochemicals
and pharmaceuticals [1, 2]. 2,3-Dihydroquinazolin-4(1H)-ones are a series of six-
membered, nitrogen-containing heterocyclic compounds that display a wide
spectrum of biological and pharmacological activities as well as medicinal
properties including anticancer [3], antitumor [4], antibiotic [5], and antihyperten-
sion action [6]. Some examples of drugs possessing quinazolinone skeleton are
shown in Fig. 1. Additionally, 2,3-dihydroquinazolinones are valuable synthetic
intermediates for preparation of biologically active 4(3H)-quinazolinones by
oxidation [7].
Two main methods, viz. (1) condensation of aldehyde or ketone with
2-aminobenzamide and (2) three-component reaction of isatoic anhydride, ammo-
nium acetate or secondary amine, and aldehyde or ketone, have been developed for
synthesis of 2,3-dihydroquinazolin-4(1H)-ones using a large number of protocols
such as Ga(OTf)3 [8], VB1 [9], ionic liquid [10], KAl(SO4)2Á12H2O [11],
ethylenediamine diacetate [12], b-CD [13], nano-In2O3 [14], CuO nanoparticles
[15], microwave (MW) irradiation [16], ZrCl4 [17], Amberlyst-15 [18], propy-
lphosphonic anhydride [19], 2-morpholinoethanesulfonic acid [20], magnetic
O
O
O
N
H N
O2S
H N
O2S
H2N
2
2
NH
NH
N
OMe
l
C
N
H
l
C
N
H
F
Quintazone
Fenquizone
Alfoqualone
N
N
N
H
C
O
N
3
O
H N
O2S
2
N
N
H
O
F
l
C
l
C
N
HN
F
Evodiamine
Alboquinazole
Fig. 1 Some examples of drugs possessing quinazolinone skeleton
123

Green protocol for synthesis of…
nanoparticles [21], b-CD-SO3H [22], and dodecylbenzenesulfonic acid [23].
Although reported protocols lead to desired products with good yields, many of
them suffer from drawbacks such as expensive reagent or catalyst, prolonged
reaction time, use of toxic solvents and catalysts, high reaction temperature,
unsatisfactory yield, and tedious workup procedure. Considering these limitations, it
is necessary to develop pioneering, efficient, convenient, and sustainable methods
for synthesis of 2,3-dihydroquinazolin-4(1H)-ones. Owing to the tremendous
consequences of chemical and industrial pollution, there is a need to minimize costs
and destructive effects on the environment [24]. In this regard, synthetic organic
chemists tend towards green chemistry strategies and develop nonpolluting and
ecocompatible procedures in their organic research [25].
Nowadays, to reduce materials that are harmful to the environment, use of
natural-based organic compounds as catalysts for organic synthesis is considered
[13, 26, 27]. Such catalysts, because of their natural origin, can be used without fear
of destructive effects on the environment. In addition, design and development of
solvent-free condition or use of sustainable solvents such as water or ethanol is very
important in terms of green chemistry [28].
Lactic acid is a chiral a-hydroxyacid produced via metabolism of sugars in
human cells, having chemical formula C3H6O3. Moreover, presence of lactic acid in
products derived from milk fermentation such as yogurt or cheese has been
confirmed [29].
To the best of our knowledge, there are few reports on use of lactic acid as
catalyst for organic transformations [30]. As part of our efforts to introduce green
and natural catalysts into organic synthesis [31–33], we report herein for the first
time use of lactic acid as safe catalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-
one derivatives.
Experimental
General
All chemicals and reagents were purchased from Merck, Fluka, and Aldrich and
used as received without further purification. Melting points were measured using
1
an Electrothermal 9100 apparatus. H and 13C nuclear magnetic resonance (NMR)
spectra were recorded on a Bruker DRX instrument in dimethyl sulfoxide (DMSO)-
d6 at 400 and 100 MHz, respectively. Thin-layer chromatography (TLC) was
performed on silica gel Polygram SILG/UV 254 plates.
General procedure for synthesis of 2,3-dihydroquinazolin-4(1H)-ones
Method A: 2-Aminobenzamide (1 mmol, 0.136 g) was added to a mixture of
aldehyde (1.2 mmol) and lactic acid (0.02 mmol, 0.018 g) and stirred at 70 °C.
123

S. Zhaleh et al.
After reaction completion (as monitored by TLC), ethanol (5 ml) was added and
stirred vigorously. Filtration of the resulting suspension afforded solid products.
Method B: In a reaction vessel, a mixture of isatoic anhydride (1 mmol, 0.163 g),
aldehyde (1.2 mmol), and ammonium acetate (1.2 mmol) as well as lactic acid
(0.02 mmol, 0.018 g) was stirred at 70 °C for appropriate time (based on TLC
monitoring). Next, similar to method A, addition of ethanol (5 ml), strong stirring,
then filtration yielded desired products.
2-(3-Fluorophenyl)-2,3-dihydroquinazolin-4(1H)-one (3d) 1H NMR (400 MHz,
DMSO-d6) d 5.75 (1H, s), 6.70 (1H, t, J = 7.2 Hz), 6.77 (1H, d, J = 8.0 Hz), 7.18
(1H, t, J = 8.4 Hz), 7.28–7.34 (3H, m), 7.42–7.47 (1H, m), 7.62 (1H, dd,
J = 1.6 Hz, J = 8.0 Hz), 8.43 (1H, br, D2O-exchange).
2-(3-Methylphenyl)-2,3-dihydroquinazolin-4(1H)-one (3q) 1H NMR (400 MHz,
DMSO-d6) d 2.32 (3H, s), 5.73 (1H, s), 6.69 (1H, t, J = 8.0 Hz), 6.76 (1H, d,
J = 8.0 Hz), 7.17 (1H, t, J = 4.0 Hz), 7.24–7.29 (4H, m), 7.33 (1H, br, D2O-
exchange), 7.63 (1H, dd, J = 1.2 Hz, J = 7.6 Hz), 8.26 (1H, br, D2O-exchange).
13C NMR (100.6 MHz, DMSO-d6) d 21.5, 67.0, 114.9, 115.3, 124.4, 127.8, 128.7,
129.6, 133.9, 138.0, 142.0, 148.3, 164.2. MS (EI, 70 eV): m/z (%) M? 238 (22), 147
(100), 120 (41), 92 (27), 65 (21), 41 (2).
2-(5-Bromo-2-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one (3s) 1H NMR
(400 MHz, DMSO-d6) d 5.98 (1H, s), 6.71 (1H, t, J = 8.0 Hz), 6.79 (1H, d,
J = 8.0 Hz), 6.85 (1H, d, J = 8.0 Hz), 7.26 (1H, dt, J = 2.0 Hz, J = 8.0 Hz), 7.34
(1H, dd, J = 2.5 Hz, J = 8.0 Hz), 7.41 (1H, br, D2O-exchange), 7.64 (1H, dd,
J = 1.6 Hz, J = 8.0 Hz), 8.06 (1H, br, D2O-exchange), 10.34 (1H, br, D2O-
exchange). 13C NMR (100.6 MHz, DMSO-d6) d 61.4, 110.4, 115.0, 115.1, 117.8,
118.1, 127.8, 130.1, 130.2, 132.4, 134.0, 148.2, 154.5, 164.4. MS (EI, 70 eV): m/
z (%) M? 318 (63), 147 (75), 120 (100), 92 (39), 63 (26), 50 (8).
2-(Naphthalen-1-yl)-2,3-dihydroquinazolin-4(1H)-one (3u) 1H NMR (400 MHz,
DMSO-d6) d 6.50 (1H, s), 6.72–6.78 (2H, m), 7.20 (1H, t, J = 8.8 Hz), 7.26–7.30
(m, 3H), 7.52–7.60 (3H, m), 7.70–7.72 (2H, m), 8.00–8.02 (2H, m), 8.31 (1H, br,
D2O-exchange), 8.56 (2H, d, J = 8.0 Hz).
2-(1-Phenylprop-1-en-2-yl)-2,3-dihydroquinazolin-4(1H)-one (3w) 1H NMR
(400 MHz, DMSO-d6) d 1.93 (3H, s), 5.33 (1H, s), 6.60 (1H, s), 6.67 (1H, t,
J = 8.0 Hz), 6.75 (1H, d, J = 8.0 Hz), 7.23–7.42 (5H, m), 7.37–7.42 (2H, m), 7.61
(1H, dd, J = 1.6 Hz), J = 8.0 Hz), 8.08 (1H, br, D2O-exchange). 13C NMR
(100.6 MHz, DMSO-d6) d 13.6, 71.9, 114.6, 117.3, 126.4, 127.4, 127.7, 128.4,
128.8, 129.0, 129.4, 130.0, 133.8, 137.1, 148.8, 164.2.
2-2-Methyl-2-phenyl-2,3-dihydroquinazolin-4(1H)-one (3x) 1H NMR (400 MHz,
DMSO-d6) d 1.65 (3H, s), 6.59 (1H, t, J = 8.0 Hz), 6.78 (1H, d, J = 8.0 Hz),
7.18–7.24 (2H, m), 7.30 (2H, t, J = 8.0 Hz), 7.48–7.51 (3H, m), 7.50 (1H, br), 8.80
(1H, br, D2O-exchange).
123

Green protocol for synthesis of…
Results and discussion
Initially, benzaldehyde (1a, 1 mmol) was treated with 2-aminobenzamide (2,
1.2 mmol) (Scheme 1) in presence of catalytic amount of lactic acid. The screening
of various conditions is listed in Table 1.
According to Table 1, increase in temperature from room temperature up to
70 °C under solvent-free condition significantly decreased the reaction time
(entries 1–6). However, reflux in EtOH and H2O showed unsatisfactory results
compared with solvent-free condition (entries 8, 9). Reaction in absence of lactic
acid yielded the product with only 40 % efficiency after 5 h (entry 7). However,
increase in the catalyst loading amount resulted in decreased reaction time
(entries 9, 10). Accordingly, solvent-free medium at 70 °C using 20 mol% lactic
acid was found to be the optimized condition. To extend the efficiency of the
catalyst for synthesis of other 2,3-dihydroquinazolin-4(1H)-one derivatives,
numerous aldehydes or ketones were transformed to corresponding products
(Scheme 2); the results are summarized in Table 2.
The obtained results show that a variety of aldehydes possessing different
functionalities provided corresponding products with good to excellent yields.
Aldehydes with electron-donating groups (p-OMe, p-NMe2, p-Me, o,p-OMe, etc.)
O
O
H
C
O
NH
NH2
NH2
+
N
H
1a
2
3a
Scheme 1 Reaction of benzaldehyde with 2-aminobenzamide
Table 1 Screening of various conditions for reaction of benzaldehyde (1.2 mmol) with 2-aminoben-
zamide (1 mmol)
Entry
Solvent
Temperature
(°C)
Catalyst
loading (mol%)
Time
(min)
Yield
(%)
1
–
r.t.
10
10
10
10
10
10
0
600
480
360
300
60
70
75
75
78
82
86
40
85
88
90
92
9
2
–
30
3
–
40
4
–
50
5
–
60
6
–
70
35
7
–
70
300
120
100
30
8
EtOH
Reflux
Reflux
70
10
10
15
20
20
9
H2O
10
11
12
–
–
–
70
20
80
20
123

S. Zhaleh et al.
O
O
O
20 mol% lactic acid
solvent-free
70°C
NH
NH2
NH2
+
R2
R2
R1
N
H
R1
1
2
3
Scheme 2 Reaction of various aldehydes with 2-aminobenzamide
Table 2 Synthesis of a variety of 2,3-dihydroquinazolin-4(1H)-one derivatives
Entry
R1
R2
Product
Time (min)
Yield (%)a
M.p. (lit. ) [Ref.]
1
Ph
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
Me
Me
3a
3b
3c
3d
3e
3f
20
35
30
22
20
25
40
30
45
40
50
110
15
25
20
30
20
50
65
45
55
40
55
190
360
92
90
90
91
92
89
85
90
88
89
85
83
91
90
92
93
90
86
84
87
89
91
84
80
82c
215–217 (218–220) [8]
195–197 (192–193) [8]
201–203 (199–200) [34]
185–187 (258–260) [35]
230–232 (233–234) [8]
187–189 (184–185) [21]
218–220 (210–211) [36]
205–207 (204–206) [36]
168–170 (167–169) [16]
214–216 (211–212) [21]
187–189 (186–187) [8]
185–187 (186–187) [39]
165–168 (200–201) [20]
190–192 (191–192) [20]
191–192 (192–194) [20]
202–204 (202–203) [34]
210–212
2
4-MeO-Ph
4-F-Ph
3
4
3-F-Ph
5
4-Me-Ph
3-Br-Ph
6
7
2-Cl-Ph
3g
3h
3i
8
4-Cl-Ph
9
2,4-Cl2-Ph
3,4-(MeO)2-Ph
2,4-(MeO)2-Ph
3,4,5-(MeO)3-Ph
4-NO2-Ph
2-NO2-Ph
3-NO2-Ph
4-Br-Ph
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
a
3j
3k
3l
3m
3n
3o
3p
3q
3r
3s
3-Me-Ph
4-NMe2-Ph
5-Br-2-OH-Ph
2-Thienyl
1-Naph
209–211 (208–210) [20]
250 decomposed
3t
217–219 (213) [38]
176–178 (–)b [40]
3u
3v
3w
3x
3y
2-Naph
220–222 (222–224) [36]
183–185 (180–182) [18]
220–222 (227–228) [37]
140–144 (184–186) [36]
a-Me-Cinn
Ph
Me
Isolated yield
b
c
In this literature, m.p. was not reported
Product formed at room temperature
gave products with good yields (Table 2, entries 2, 10–12, 18). Aldehydes having
electron-withdrawing groups (p-NO2, o-NO2, etc.) also gave corresponding products
with satisfactory yields (Table 2, entries 13–15). Other aldehydes such as those
123

Green protocol for synthesis of…
containing halogen functionality (Table 2, entries 3, 4, 6–8), heterocyclic (Table 2,
entry 20), bicyclic (Table 2, entries 21, 22), a,b-unsaturated (Table 2, entry 23) or
possessing different groups (Table 2, entry 19) also showed proper yields. The
above observations reveal that the efficiency of the catalyst was so good that only
slight differences in yield and reaction time were seen on functional group changes.
To emphasize the ability of lactic acid for synthesis of 2,3-dihydroquinazolin-
4(1H)-ones, when we utilized ketones as reactant instead of aldehydes, we found
that both acetone and acetophenone, as representative small and large ketones,
respectively, provided corresponding products in high yields, although the reaction
times were longer than for aldehydes (Table 2, entries 24, 25). For acetone, because
of its low boiling point, the reaction occurred at room temperature.
As stated earlier, 2,3-dihydroquinazolin-4(1H)-ones can also be prepared by
three-component reaction of isatoic anhydride, aldehydes, and ammonium acetate.
To survey the potency of lactic acid for promotion of this reaction, we treated isatoic
anhydride 4 with benzaldehyde and ammonium acetate 5 using the aforementioned
optimized condition; the product was formed in 90 % yield.
To confirm the versatility of the reaction, a similar procedure was performed for
some other aldehydes (Scheme 3); the results are listed in Table 3.
Plausible mechanisms for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones
using both the first and second method are depicted in Scheme 4 [23, 41]. As is
obvious from the illustrated mechanisms, the acidic property of lactic acid is
supposed to play an essential role in accelerating the formation of the corresponding
products. For Method A, the reaction proceeds via protonation of aldehyde and
imine intermediate. On the other hand, in Method B, protonation of isatoic
anhydride facilitates addition of ammonia group. Then, elimination of CO2 gives
anthranilic acid and the reaction continues as before.
O
O
O
solvent-free
NH
O
+
+
NH4OAC
R1
R2
R2
R1
20 mol% lactic acid
70°C
N
H
N
H
4
O
5
1
3
Scheme 3 Three-component reaction of aldehyde, isatoic anhydride, and ammonium acetate
Table 3 Three-component
synthesis of 2,3-
dihydroquinazolin-4(1H)-ones
Entry
R1
R2
Time (min)
Yield (%)a
1
2
3
4
5
Ph
H
30
60
90
84
89
92
81b
4-NMe2-Ph
4-NO2-Ph
4-Br-Ph
Me
H
H
25
a
Isolated yield
H
35
b
Product formed at room
temperature
Me
220
123

S. Zhaleh et al.
Method A:
H
O
O
O
O
+
NH2
-
H
NH
H
+
NH2
NH2
N
H
N
H
Method B:
H
O
O
H
O
H
O
NH2
NH3
O
+
+
H
NH4OAC
O
O
H
O
N
H
O
N
H
O
NH
O
NH
O
+
-
H
-
CO
2
H
O
O
O
O
H
NH2
NH2
NH2
NH2
-
H
2O
H
O
N
H
N
H2
O
O
+
-
H
NH
NH
N
H
N
H2
Scheme 4 Mechanisms for synthesis of 2,3-dihydroquinazolin-4(1H)-ones
Conclusions
We have developed an efficient, simple, and ecofriendly approach for synthesis of
2,3-dihydroquinazolin-4(1H)-ones. In this work, lactic acid was employed as green,
inexpensive catalyst under solvent-free condition to abide by the principles of green
chemistry. A wide variety of 2,3-dihydroquinazolin-4(1H)-one derivatives were
synthesized by two methods utilizing 2-aminobenzamide or isatoic anhydride as
starting material. The results show that lactic acid promoted formation of the desired
products for aliphatic, aromatic, and heterocyclic aldehydes. More importantly,
ketones also yielded corresponding products. The main features of these two
procedures are safe catalyst, absence of toxic and volatile solvents, short reaction
time, as well as repeatability and universality for various aldehydes and ketones.
123

Green protocol for synthesis of…
Acknowledgments The University of Sistan and Baluchestan is thanked for financial support of this
work. We also thank Dr. M. R. Faghihi, postdoctoral researcher of the university, for his scientific
contribution to this work.
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