Acetic acid-promoted, efficient, one-pot synthesis of 2,3- dihydroquinazolin-4(1H)-ones

Article abstract of DOI:10.1007/s00706-011-0494-6

A simple, efficient, and general method has been developed for one-pot, three-component synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives based on a condensation reaction strategy of isatoic anhydride, aldehydes, and amines using acetic acid under reflux conditions.

Full text of DOI:10.1007/s00706-011-0494-6

Monatsh Chem (2011) 142:631–635
DOI 10.1007/s00706-011-0494-6
ORIGINAL PAPER
Acetic acid-promoted, efficient, one-pot synthesis
of 2,3-dihydroquinazolin-4(1H)-ones
•
Zahed Karimi-Jaberi Reza Arjmandi
Received: 30 September 2010 / Accepted: 30 March 2011 / Published online: 21 April 2011
Ó Springer-Verlag 2011
Abstract A simple, efficient, and general method has
been developed for one-pot, three-component synthesis of
2,3-dihydroquinazolin-4(1H)-one derivatives based on a
condensation reaction strategy of isatoic anhydride, alde-
hydes, and amines using acetic acid under reflux conditions.
context, some methods and catalysts have been reported
[11–22]. Developing versatile approaches towards synthe-
sis of 2,3-dihydroquinazolin-4(1H)-ones still remains a
highly desired goal in organic synthesis.
In view of our ongoing efforts to explore newer reac-
tions for synthesis of heterocyclic compounds [23–25], we
decided to investigate the possibility of synthesizing 2,3-
dihydroquinazolin-4(1H)-one derivatives based on a one-
pot three-component condensation reaction strategy of
isatoic anhydride, aldehydes, and amines using acetic acid
(Scheme 1).
Keywords 2,3-Dihydroquinazolin-4(1H)-ones Á
Isatoic anhydride Á Acetic acid Á Aldehydes Á Amines
Introduction
In the mainstream of current interest, multicomponent
reactions (MCRs) have been proven to be a very elegant
and rapid way to access complex structures in a single
synthetic operation from simple building blocks, showing
high atom economy and high selectivity [1–3].
Results and discussion
To optimize the reaction conditions, the reaction between
benzaldehyde, aniline, and isatoic anhydride was used as a
model reaction. The optimized reactant ratios were found
to be 1.0 equiv. benzaldehyde, 1.1 equiv. aniline, and 1.0
equiv. isatoic anhydride in the presence of 5 cm3 acetic
acid. The expected 2,3-diphenylquinazolin-4(1H)-one was
produced in 79% yield after 2.5 h under reflux in acetic
acid. To establish the generality and scope of the acetic
acid-promoted 2,3-dihydroquinazolin-4(1H)-one synthesis,
the reaction was examined with various structurally diverse
aldehydes, amines, and isatoic anhydride. The results are
summarized in Table 1. The structure of the products was
2,3-Dihydroquinazolines are an important class of het-
erocycles with a wide range of pharmacological and
biological activities [4, 5]. Additionally, these compounds
can easily be oxidized to their quinazolin-4(3H)-one ana-
logs, which are themselves important biologically active
compounds [6, 7]. Thus, efficient synthesis of these com-
pounds has been of great interest in recent years. A number
of synthetic methods for 2,3-dihydroquinazolin-4(1H)-ones
have been developed during the past two decades [8–10].
One-pot three-component condensation of isatoic anhy-
dride, aldehydes, and amines is the most convenient
method for preparation of these compounds. In this
O
O
R2
N
O
AcOH
+
R1CHO + R2NH2
Z. Karimi-Jaberi (&) Á R. Arjmandi
Department of Chemistry, Islamic Azad University,
Firoozabad Branch, P.O. Box 74715-117,
Firoozabad, Fars, Iran
N
R1
N
O
H
H
e-mail: zahed.karimi@yahoo.com
Scheme 1
123

632
Z. Karimi-Jaberi, R. Arjmandi
Table 1 Synthesis of 2,3-dihydroquinazolin-4(1H)-ones
Comp. R1
R2
Time Yield M.p.
(h)
Ref.
(%) (°C)
1
Ph
Ph
Ph
Ph
Ph
Ph
Ph
2.5
79
92
92
91
89
93
93
91
82
85
88
85
88
88
86
91
89
90
93
91
97
82
209–211 [11]
186–188 [11]
195–197 [11]
179–181 [22]
226–228 [11]
136–138 [22]
2
3-O2NC6H4
4-O2NC6H4
2-O2NC6H4
4-ClC6H4
2-ClC6H4
1.5
3
1.5
4
1.5
5
2
Scheme 2
6
2
7
2,6-Cl2C6H3 Ph
2,4-Cl2C6H3 Ph
2-Cl-6-FC6H3 Ph
1.5
234–236
189–191
208–210
–
–
–
respect to reaction times and yields of the obtained prod-
ucts. Thus, the present protocol with acetic acid as a
catalyst is an alternate route for production of 2,3-dihy-
droquinazolin-4(1H)-ones.
8
1.5
9
1.5
10
11
12
13
14
15
16
17
18
19
20
21
22
Ph
PhCH2
1
160–162 [11]
3-O2NC6H4
2-O2NC6H4
2-ClC6H4
PhCH2
PhCH2
PhCH2
2
153–155
133–135
174–176
206–208
213–215
175–177
174–176
205–207
174–176
184–186
141–143
203–205
–
–
–
–
–
–
–
–
–
–
–
–
In conclusion, this paper describes a convenient and
efficient process for synthesis of 2,3-dihydroquinazolin-
4(1H)-ones by one-pot reaction of isatoic anhydride,
aldehydes, and amines using acetic acid under reflux con-
ditions. Several derivatives of the title compounds with
different substituents were synthesized to show the diver-
sity of the method. The method offers several advantages,
such as the lack of any toxic solvent or catalyst, simplicity
of performance, low cost, and improved yields. Starting
materials are inexpensive and commercially available.
1
1.5
2,3-Cl2C6H3 PhCH2
2-Cl-6-FC6H3 PhCH2
1.5
1
2
Ph
2-ClC6H4CH2
3-O2NC6H4
4-O2NC6H4
2-ClC6H4
2-ClC6H4CH2 2.5
2-ClC6H4CH2
2-ClPhCH2
1
1
1
1
1
2,6-Cl2C6H3 2-ClC6H4CH2
2,4-Cl2C6H3 2-ClC6H4CH2
2-Cl-6-FC6H3 2-ClC6H4CH2
Experimental
deduced from their infrared (IR), 1H nuclear magnetic
resonance (NMR), 13C NMR, and elemental analysis.
The reaction can also proceed with several functional-
ities present on the aromatic amine, such as halogen and
nitro groups. The reaction has also been done with various
benzyl amines. In all these cases, the corresponding 2,3-
dihydroquinazolines were obtained in good yields. It is
important to note that, in the absence of acetic acid, the
reaction yield was too low even at 120 °C after 5 h.
The mechanism of this reaction is believed to proceed
through condensation of isatoic anhydride with amine
followed by decarboxylation to yield the corresponding
2-aminobenzamide. Condensation of the aldehyde with the
amino group of 2-aminobenzamide then gives an imine
which undergoes cyclization to afford the 2,3-dihydroqui-
nazoline product as shown in Scheme 2 [11].
Products were characterized by comparison of their phys-
ical and spectral data with those of authentic samples. All
yields refer to isolated products after recrystallization. IR
and NMR spectra were recorded on PerkinElmer 781 and
Bruker DPX400 machines. The progress of the reactions
was monitored by thin-layer chromatography (TLC).
General procedure for preparation
of 2,3-dihydroquinazolin-4(1H)-ones
A mixture of aldehyde (1 mmol), amine (1.1 mmol), and
isatoic anhydride (1 mmol) in 5 cm3 acetic acid was stirred
under reflux for the appropriate time indicated in Table 1.
After completion of the reaction, as indicated by TLC
(ethyl acetate/n-hexane, 1/2), the reaction mixture was
poured into 20 cm3 ice water. On solidification, it was
filtered, washed with ice water, and recrystallized from
ethanol to give the pure 2,3-dihydroquinazolin-4(1H)-ones.
To show the merit of the present work in comparison
with results reported in the literature, we compared results
of acetic acid with montmorillonite K-10 [12], silica sul-
furic acid [14], KAl(SO4)2Á12H2O (alum) [11], Zn(PFO)2
[16], Ga(OTf)3 [13], and copolymer-PTSA (para-toluene-
sulfonic acid) [18] as catalysts in the reaction of isatoic
anhydride, aniline, and benzaldehyde in the synthesis of
2,3-dihydro-2-phenylquinazolin-4(1H)-one. As shown in
Table 2, acetic acid can act as an effective catalyst with
2-(2,6-Dichlorophenyl)-2,3-dihydro-3-phenylquinazolin-
4(1H)-one (7, C20H14Cl2N2O)
1H NMR (CDCl3): d = 4.43 (br, 1H, NH), 6.65 (d, J =
8.0 Hz, 1H, CH), 6.88–6.92 (m, 1H, Ar–H), 7.09–7.27
(m, 6H, Ar–H), 7.29–7.43 (m, 4H, Ar–H), 8.02–8.05 (m,
1H, Ar–H) ppm; 13C NMR (CDCl3): d = 70.68, 114.05,
123

Acetic acid-promoted, efficient, one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones
633
Table 2 Comparison of efficiency of various catalysts in the reaction of isatoic anhydride, aniline, and benzaldehyde
Entry
Catalyst
Conditions
Time (h)
Yield (%)
Ref.
1
2
3
4
5
6
7
Montmorillonite K-10 (0.3 g)
Silica sulfuric acid, 20 mol% (0.06 g)
KAl(SO4)2Á12H2O (alum, 0.2 g)
[Zn(PFO)2] (0.027 g, 0.03 mmol)
Ga(OTf)3 (1 mol%)
EtOH, reflux
6.5
5
80
80
78
82
79
82
79
[12]
[14]
[11]
[16]
[13]
[18]
–
Solvent-free, 80 °C
EtOH, reflux
4
H2O/EtOH (1/3), reflux
EtOH, reflux
6
1
Copolymer-PTSA (0.3 g)
Acetic acid
EtOH, reflux
6.5
2.5
Reflux
115.03, 118.95, 127.30, 127.53, 128.66, 129.00, 129.56,
130.51, 132.53, 133.92, 135.99, 138.69, 145.79, 163.24 ppm.
(s, 1H, CH), 6.51 (d, J = 8.0 Hz, 1H, Ar–H), 6.86–6.89
(m, 1H, Ar–H), 7.25–7.32 (m, 6H, Ar–H), 7.55–7.56 (m,
2H, Ar–H), 7.58–7.60 (m, 1H, Ar–H), 8.04–8.07 (m, 2H,
Ar–H) ppm; 13C NMR (CDCl3): d = 48.06, 66.25, 114.76,
114.98, 119.31, 125.93, 127.91, 127.95, 128.06, 128.68,
128.86, 129.81, 134.06, 134.37, 134.77, 135.79, 143.96,
147.78, 163.73 ppm.
2-(2,4-Dichlorophenyl)-2,3-dihydro-3-phenylquinazolin-
4(1H)-one (8, C20H14Cl2N2O)
1H NMR (CDCl3): d = 5.21 (br, 1H, NH), 6.42 (s, 1H,
CH), 6.62 (d, J = 8.0 Hz, 1H, Ar–H), 6.89–6.94 (m, 1H,
Ar–H), 7.21–7.29 (m, 3H, Ar–H), 7.31–7.40 (m, 3H, Ar–
H), 7.40–7.43 (m, 1H, Ar–H), 7.52–7.55 (m, 1H, Ar–H),
7.90 (d, J = 8.0 Hz, 1H, Ar–H), 8.05 (d, J = 1.2 Hz, 1H,
Ar–H) ppm; 13C NMR (CDCl3): d = 70.76, 114.95,
116.56, 119.90, 125.71, 126.89, 127.59, 129.06, 129.11,
130.17, 132.19, 134.19, 135.41, 135.48, 140.57, 144.46,
163.10 ppm.
3-Benzyl-2-(2-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-
one (13, C21H17ClN2O)
1H NMR (CDCl3): d = 3.69 (d, J = 15.2 Hz, 1H, CH2),
4.98 (br, 1H, NH), 5.72 (d, J = 15.2 Hz, 1H, CH2), 6.03
(s, 1H, CH), 6.51 (d, J = 8.0 Hz, 1H, Ar–H), 6.85–6.89
(m, 1H, Ar–H), 7.21–7.41 (m, 10H, Ar–H), 8.04
(dd, J = 1.2 Hz, J = 7.8 Hz, 1H, Ar–H) ppm; 13C NMR
(CDCl3): d = 47.64, 67.27, 114.63, 115.61, 119.30,
127.34, 127.42, 127.70, 128.08, 128.69, 128.76, 130.13,
130.32, 132.11, 133.76, 136.07, 136.50, 144.54,
163.65 ppm.
2-(2-Chloro-6-fluorophenyl)-2,3-dihydro-3-phenyl-
quinazolin-4(1H)-one (9, C20H14ClFN2O)
1H NMR (CDCl3): d = 4.65 (br, 1H, NH), 6.67 (d,
J = 8.0 Hz, 1H, CH), 6.91–6.96 (m, 2H, Ar–H),
7.11–7.14 (m, 1H, Ar–H), 7.17–7.25 (m, 3H, Ar–H), 7.28
(d, J = 2.8 Hz, 2H, Ar–H), 7.29 (d, J = 3.6 Hz, 2H, Ar–
H), 7.31–7.37 (m, 1H, Ar–H), 8.05–8.08 (m, 1H, Ar–H)
ppm; 13C NMR (CDCl3): d = 69.47, 114.49, 115.54,
115.77, 119.60, 126.06, 126.09, 127.10, 127.38, 128.98,
130.78, 130.88, 133.63, 134.13, 139.55, 145.37, 160.51,
163.03 ppm.
3-Benzyl-2-(2,3-dichlorophenyl)-2,3-dihydroquinazolin-
4(1H)-one (14, C21H16Cl2N2O)
1H NMR (CDCl3): d = 3.67 (d, J = 15.2 Hz, 1H, CH2),
5.03 (br, 1H, NH), 5.72 (d, J = 15.2 Hz, 1H, CH2), 6.03 (s,
1H, CH), 6.51 (d, J = 8.0 Hz, 1H, Ar–H), 6.85–6.89 (m,
1H, Ar–H), 7.13–7.46 (m, 9H, Ar–H), 8.03–8.05 (m, 1H,
Ar–H) ppm; 13C NMR (CDCl3): d = 47.71, 67.64, 114.74,
115.47, 119.46, 125.43, 127.83, 127.84, 128.12, 128.70,
128.82, 130.28, 130.83, 133.90, 134.12, 136.26, 138.47,
144.27, 163.50 ppm.
3-Benzyl-2,3-dihydro-2-(3-nitrophenyl)quinazolin-4(1H)-
one (11, C21H17N3O3)
1H NMR (CDCl3): d = 3.86 (d, J = 15.6 Hz, 1H, CH2),
5.57 (d, J = 15.6 Hz, 1H, CH2), 5.76 (s, 1H, CH), 6.60 (d,
J = 8.0 Hz, 1H, Ar–H), 6.92–6.96 (m, 1H, Ar–H), 7.23–7.27
(m, 2H, Ar–H), 7.28–7.35 (m, 4H, Ar–H), 7.48–7.52 (m, 1H,
Ar–H), 7.67 (d, J = 8.0 Hz, 1H, Ar–H), 8.05–8.18 (m, 3H,
Ar–H) ppm; 13C NMR (CDCl3): d = 47.52, 70.09, 114.88,
115.81, 119.86, 121.83, 124.02, 127.77, 127.92, 128.81,
128.84, 130.04, 132.23, 134.04, 136.21, 141.74, 144.50,
148.36, 163.09 ppm.
3-Benzyl-2-(2-chloro-6-fluorophenyl)-2,3-dihydroquinazo-
lin-4(1H)-one (15, C21H16ClFN2O)
1H NMR (CDCl3): d = 3.84 (d, J = 15.2 Hz, 1H, CH2),
4.43 (br, 1H, NH), 5.50 (d, J = 15.2 Hz, 1H, CH2), 6.40 (s,
1H, CH), 6.85–6.89 (m, 1H, Ar–H), 6.91–6.96 (m, 1H,
Ar–H), 7.20–7.29 (m, 9H, Ar–H), 8.05 (dd, J = 1.6 Hz,
J = 1.6 Hz, 1H, Ar–H) ppm; 13C NMR (CDCl3):
d = 47.13, 66.39, 113.74, 115.79, 116.03, 119.01,
126.08, 126.12, 127.58, 128.24, 128.56, 128.61, 130.59,
130.69, 133.36, 136.46, 144.71, 160.65, 163.05, 163.08,
163.17 ppm.
3-Benzyl-2,3-dihydro-2-(2-nitrophenyl)quinazolin-4(1H)-
one (12, C21H17N3O3)
1H NMR (CDCl3): d = 3.72 (d, J = 15.2 Hz, 1H, CH2),
5.32 (br, 1H, NH), 5.61 (d, J = 15.2 Hz, 1H, CH2), 6.21
123

634
Z. Karimi-Jaberi, R. Arjmandi
3-(2-Chlorobenzyl)-2,3-dihydro-2-phenylquinazolin-
4(1H)-one (16, C21H17ClN2O)
J = 8.0 Hz, 1H, CH), 6.79 (s, 1H, Ar–H), 6.79–6.89 (m,
1H, Ar–H), 7.13–7.43 (m, 8H, Ar–H), 8.04 (dd,
J = 1.6 Hz, J = 1.2 Hz, 1H, Ar–H) ppm; 13C NMR
(CDCl3): d = 43.68, 68.61, 113.56, 114.20, 118.58,
127.04, 128.49, 128.77, 129.55, 129.44, 130.62, 132.07,
133.30, 133.58, 133.79, 133.89, 136.12, 145.61,
163.51 ppm.
1H NMR (CDCl3): d = 4.11 (d, J = 16.0 Hz, 1H, CH2),
5.45 (d, J = 16.0 Hz, 1H, CH2), 5.72 (s, 1H, CH), 6.57 (d,
J = 8.0 Hz, 1H, Ar–H), 6.89–6.93 (m, 1H, Ar–H),
7.20–7.29 (m, 2H, Ar–H), 7.30–7.59 (m, 8H, Ar–H), 8.05
(dd, J = 1.6 Hz, J = 1.2 Hz, 1H, Ar–H) ppm; 13C NMR
(CDCl3): d = 44.93, 71.78, 114.51, 115.74, 119.32,
126.42, 127.11, 128.58, 128.76, 129.00, 129.15, 129.35,
129.48, 133.43, 133.77, 134.31, 139.25, 145.25,
163.40 ppm.
3-(2-Chlorobenzyl)-2-(2,4-dichlorophenyl)-2,3-
dihydroquinazolin-4(1H)-one (21, C21H15Cl3N2O)
1H NMR (CDCl3): d = 4.05 (d, J = 16.0 Hz, 1H, CH2),
5.01 (br, 1H, NH), 5.57 (d, J = 16.0 Hz, 1H, CH2), 6.04 (s,
1H, CH), 6.54 (d, J = 8.0 Hz, 1H, Ar–H), 6.87–6.91 (m,
1H, Ar–H), 7.16–7.44 (m, 7H, Ar–H), 7.56 (dd,
J = 2.0 Hz, J = 7.8 Hz, 1H, Ar–H), 8.02 (dd,
J = 1.6 Hz, J = 8.0 Hz, 1H, Ar–H) ppm; 13C NMR
(CDCl3): d = 45.52, 67.63, 114.80, 115.56, 119.83,
127.33, 127.60, 128.07, 128.71, 129.02, 129.39, 129.59,
130.23, 132.78, 133.70, 133.88, 134.01, 134.65, 135.40,
144.38, 163.65 ppm.
3-(2-Chlorobenzyl)-2,3-dihydro-2-(3-nitrophenyl)-
quinazolin-4(1H)-one (17, C21H16ClN3O3)
1H NMR (CDCl3): d = 4.27 (d, J = 16.0 Hz, 1H, CH2),
5.41 (d, J = 16.0 Hz, 1H, CH2), 5.85 (s, 1H, CH), 6.62 (d,
1H, J = 8.0 Hz, Ar–H), 6.93–6.95 (m, 1H, Ar–H),
7.22–7.35 (m, 4H, Ar–H), 7.48–7.52 (m, 2H, Ar–H),
7.67–7.69 (m, 1H, Ar–H), 8.05–8.07 (m, 1H, Ar–H),
8.15–8.20 (m, 2H, Ar–H) ppm; 13C NMR (CDCl3):
d = 45.13, 70.73, 114.98, 116.03, 120.14, 121.78,
124.10, 127.33, 128.92, 128.99, 129.56, 129.67, 130.06,
132.11, 133.43, 133.87, 134.10, 141.51, 144.37, 148.39,
163.13 ppm.
3-(2-Chlorobenzyl)-2-(2-chloro-6-fluorophenyl)-2,3-
dihydroquinazolin-4(1H)-one (22, C21H15Cl2FN2O)
1H NMR (CDCl3): d = 4.17 (d, J = 16.0 Hz, 1H, CH2),
4.72 (br, 1H, NH), 5.49 (d, J = 16.0 Hz, 1H, CH2), 6.40 (s,
1H, CH), 6.56 (d, J = 8.0 Hz, 1H, Ar–H), 6.87–6.98 (m,
2H, Ar–H), 7.19–7.29 (m, 4H, Ar–H), 7.30–7.49 (m, 3H,
Ar–H), 8.06 (dd, J = 1.6 Hz, J = 1.2 Hz, 1H, Ar–H) ppm;
13C NMR (CDCl3): d = 44.64, 66.98, 113.99, 115.89,
116.13, 119.28, 126.21, 126.24, 127.16, 128.67, 128.72,
129.43, 129.51, 130.64, 130.74, 133.44, 133.66, 133.85,
144.77, 160.45, 162.97, 163.39 ppm.
3-(2-Chlorobenzyl)-2,3-dihydro-2-(4-nitrophenyl)-
quinazolin-4(1H)-one (18, C21H16ClN3O3)
1H NMR (CDCl3): d = 4.19 (d, J = 16.0 Hz, 1H, CH2),
5.49 (d, J = 16.0 Hz, 1H, CH2), 5.81 (s, 1H, CH), 6.60 (d,
J = 8.0 Hz, 1H, Ar–H), 6.93–6.96 (m, 1H, Ar–H),
6.97–7.28 (m, 2H, Ar–H), 7.29–7.36 (m, 2H, Ar–H),
7.48–7.52 (m, 3H, Ar–H), 8.05 (dd, J = 1.2 Hz,
J = 1.6 Hz, 1H, Ar–H), 8.17 (d, J = 8.0 Hz, 2H, Ar–H)
ppm; 13C NMR (CDCl3): d = 45.18, 70.51, 114.98,
116.02, 120.17, 124.22, 127.24, 127.35, 128.88, 129.09,
129.62, 129.69, 133.55, 133.83, 134.13, 144.20, 146.29,
148.32, 163.00 ppm.
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123

Acetic acid-promoted, efficient, one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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