Synthesis of new 2-aryl substituted 2,3-dihydroquinazoline-4(1H)-ones under solvent-free conditions, using molecular iodine as a mild and efficient catalyst

Article abstract of DOI:10.1080/00397910802178427

A simple, inexpensive, and efficient one-pot synthesis of 2,3-dihydroquinazoline-4(1H)-one derivatives under solvent-free conditions using a catalytic amount of iodine with excellent product yields is reported. This methodology provides easy, quantitative

Full text of DOI:10.1080/00397910802178427

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Synthesis of New 2-
Aryl Substituted 2,3-
Dihydroquinazoline-4(1H)-ones
Under Solvent-Free Conditions,
Using Molecular Iodine as a Mild
and Efficient Catalyst
a
Shahnaz Rostamizadeh , Ali Mohammad Amani
a
a
a
,
Reza Aryan , Hamid Reza Ghaieni & Nasrin
a
Shadjou
a
Department of Chemistry, Faculty of Sciences, K.
N. Toosi University of Technology, Tehran, Iran
Version of record first published: 29 Sep 2008
To cite this article: Shahnaz Rostamizadeh, Ali Mohammad Amani, Reza Aryan, Hamid
Reza Ghaieni & Nasrin Shadjou (2008): Synthesis of New 2-Aryl Substituted 2,3-
Dihydroquinazoline-4(1H)-ones Under Solvent-Free Conditions, Using Molecular Iodine
as a Mild and Efficient Catalyst, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 38:20, 3567-3576
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1
Synthetic Communications , 38: 3567–3576, 2008
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397910802178427
Synthesis of New 2-Aryl Substituted
,3-Dihydroquinazoline-4(1H)-ones Under
2
Solvent-Free Conditions, Using Molecular Iodine
as a Mild and Efficient Catalyst
Shahnaz Rostamizadeh, Ali Mohammad Amani, Reza Aryan,
Hamid Reza Ghaieni, and Nasrin Shadjou
Department of Chemistry, Faculty of Sciences, K. N. Toosi University of
Technology, Tehran, Iran
Abstract: A simple, inexpensive, and efficient one-pot synthesis of 2,3-dihydro-
quinazoline-4(1H)-one derivatives under solvent-free conditions using a catalytic
amount of iodine with excellent product yields is reported. This methodology
provides easy, quantitative access to various 2,3-dihydroquinazoline-4(1H)-one
derivatives, using commercially available iodine as a catalyst.
Keywords: 2,3-Dihydroquinazolinone heterocycles, molecular iodine, multicom-
ponent reactions, solvent-free condition
Quinazolinone and quinazolinedione derivatives are of considerable
[
interest because of their wide range of pharmacological properties.
1–9]
Several quinazolinone derivatives have also been reported to exhibit
analgesic, anesthetic, antibacterial, anticancer, anticonvulsant, antihyper-
tensive, anti-inflammatory, antimalerial, antiparasitic, antiviral, diuretic,
[
10]
muscle relaxant, and sedative properties.
Methaqualone
nazolinone drug, first launched in 1951,
[11–13]
is probably the most well-known synthetic qui-
and its application includes
[14]
Received February 5, 2008.
Address correspondence to Shahnaz Rostamizadeh, Department of Chemis-
try, Faculty of Sciences, K. N. Toosi University of Technology, P. O. Box
1
5875-4416, Tehran, Iran. E-mail: shrostamizadeh@yahoo.com
3
567

3568
S. Rostamizadeh et al.
Figure 1. Methaqualone structure.
[
15]
sedation and hypnosis as somewhat modified etaqualone
and metha-
[
qualone analogs (Fig. 1).
16]
In view of these useful properties, development of a simple, efficient,
and general synthetic method for these widely used organic compounds
from readily available reagents is one of the major challenges in organic
synthesis. Thus, a reaction that uses a catalytic amount of readily avail-
able iodine should greatly contribute to the creation of environmentally
[
17–27]
benign processes. In recent years, the use of molecular iodine
has
received considerable attention as an mild, inexpensive, nontoxic, readily
available Lewis acid catalyst for various organic transformations such as
[
21]
[22]
Michael addition, coupling reaction, cycloaddition, silylation,
[23]
[24]
[25]
[26]
protection=deprotection,
and even multicomponent synthesis,
in
which it can efficiently activate C¼C, C¼O, C¼N, and other functional
groups. To the best of our knowledge, no examples of iodine-catalyzed
synthesis of quinazolinones have been reported in the literature. MCRs
leading to interesting heterocycles are particularly useful for the
creation of diverse chemical libraries of drug-like molecules for biological
[
28]
screening.
We report for the first time preparation of 2,3-dihydroquinazolin-
(1H)-ones via multicomponent reactions catalyzed by iodine under mild
conditions.
4
When a mixture of isatoic anhydride (1), an aromatic aldehyde (2),
ꢀ
ammonium acetate, and a catalytic amount of I was stirred at 110 C
2
under solvent-free conditions, the corresponding 2,3-dihydroquinazolin-
4
(1H)-ones (4a–n) were obtained in excellent yield (Scheme 1, Table 1).
The reactions were completed smoothly within 4 to 25 min, and the
products were isolated by a simple workup procedure. Thus an easy
and green method for the synthesis of a novel class of the quinazolinone
family is introduced. The reaction did not proceed well in the absence of
I2; also, when other amines such as ethylamine, methylamine, and aniline
were applied in place of ammonium acetate, satisfactory results were not
achieved.
Molecular iodine is an efficient and green catalyst for the synthesis of
,3-dihydroquinazolinones. Very recently, formation of 2,3-disubstituted
2

Synthesis of New Substituted 2,3-Dihydroquinazolinones
3569
Scheme 1. Synthesis of new substituted 2,3-dihydroquinazolinones.
quinazolin-4(3H)-ones via multicomponent reactions has been reported
[
29–32]
in the literature.
We believe that many biologically active derivatives
could be synthesized by this multicomponent reaction with high atomic
economy. Herein, a three-component, one-step synthesis of 2,3-dihydro-
quinazolin-4(1H)-ones using iodine, which is relatively nontoxic and
inexpensive, is at the center of our study. In the course of our work on
applications of iodine in organic reactions, we have found that it is an
effective promoter as well as an ecofriendly and efficient catalyst for
the synthesis of 2,3-dihydroquinazolin-4(1H)-ones. It seems that the reac-
tion proceeds through condensation of isatoic anhydride 1 ammonium
Table 1. Synthesis of 2-aryl substituted 2,3-dihydroquinazoline-4(1H)-ones in the
presence of molecular iodine
ꢀ
Mp ( C)
a
Product
Ar
Time (min) Yield (%)
Found
Reported
4
4
2
2
2
2
2
2
2
2
2
2
2
4
a
b
3-NO C H
2
8
8
4
5
5
4
5
4
10
25
15
15
20
5
94
94
97
95
99
98
94
98
97
98
98
98
97
98
180–182
310–312
350–351
238–240
195–197
230–231
232–233
279–280
207–208 198–200
229–231 233–234
173–175 165–167
183–184 178–180
225–226 218–220
229–230 231–232
—
—
—
—
—
—
—
—
6
4
4
4-NO
2
C
6
H
4c
4d
4e
4f
4g
4h
4i
4j
4k
4l
4-CNC
4-PhCH -O-C H
4
6
H
4
2
6
4-BrC
2-ClC
2,3-Cl C H
6
H
4
6
H
4
2
6
3
4-FC
4-ClC
6
H
4
[
[
[
[
[
[
33]
6
H
4
29]
30]
30]
30]
30]
4-MeC H4
6
2-MeOC H
6
4
6
4-MeOC H
4
4m
n
6 5
C H
3-BrC H4
6
a
Isolated yields.

3570
S. Rostamizadeh et al.
Scheme 2. Formation of new substituted 2,3-dihydroquinazolinones.
acetate 2, followed by decarboxylation, to yield the corresponding
-aminobenzamide 3. Condensation of the aromatic aldehyde with
2
ammonium acetate gives imine 4, which undergoes cyclization to afford
the dihydroquinazoline product 5 (Scheme 2).
In conclusion, in this report, iodine has been employed as an appro-
priate catalyst for the one-pot multicomponent synthesis of 2,3-dihydro-
quinazolin-4(1H)-ones on the basis of its (a) high efficiency, (b) easy
availability, (c) low cost, (d) operational simplicity, and (e) action under
mild reaction conditions. The products were formed in excellent yields
with short reaction times. This method offers several advantages, such
as omitting any toxic solvent or catalyst, very simple workup without
using any chromatographic method for purification of products, and
improved yields. Starting materials are also inexpensive and commer-
cially available.
EXPERIMENTAL
Melting points were recorded on a Buchi B-540 apparatus. IR spectra
were recorded on an ABB Bomem Model FTLA200-100 instrument.
1
13
H and C NMR spectra were measured with a Bruker DRX-300
Avance spectrometer at 300 and 75 MHz using TMS as an internal
standard. Chemical shifts (d) are reported relative to TMS, and coupling
constants (J) are reported in hertz (Hz). Mass spectra were recorded on
a Shimadzu QP 1100 EX mass spectrometer with 70-eV ionization
potential. Elemental analyses of new compounds were performed with
a Vario EL III 0 instrument.

Synthesis of New Substituted 2,3-Dihydroquinazolinones
3571
General Procedure for the Synthesis of 2,3-Dihydroquinazolin-
4
(1H)-ones
A mixture of isatoic anhydride (1 mmol), aromatic aldehyde (1 mmol),
and ammonium acetate (1.2 mol) was added to 0.05 g (0.2 mmol) of mole-
ꢀ
cular iodine (20 mol%) and stirred at 110 C for an appropriate period of
time (Table 1). When the reaction was completed (measured by thin-layer
chromatography, TLC; n-hexane–EtOAc, 2:1), the mixture was treated
with a solution of aqueous Na S O . The precipitated solids were filtered
2
2
3
off and finally recrystallized from ethanol. Products 4j–n are known com-
1
pounds, and their physical data, IR, and H NMR spectra were essen-
tially identical with those of authentic samples. Other products, which
13
1
are new compounds, were characterized by IR, H and C NMR, and
mass spectroscopy.
Spectral Data for Some New Compounds
Compound 4a
ꢁ
1
ꢁ1
1
IR (KBr, cm ): 1608, 2910, 3050,3245, 3350 cm ; H-NMR (300 MHz,
CDCl ): d ¼ 6.66 (t, 1H, J ¼ 6.0 Hz, CH), 6.77 (d, 1H, J ¼ 6.0 Hz, CH),
3
7
.26 (d, t J ¼ 1.2 Hz, J ¼ 9.0 Hz, 1H, CH), 7.33 (s, 1H, NH), 7.59
1
2
(
d, 1H, J ¼ 9.0 Hz, CH), 7.69 (t, J ¼ 6.0 Hz, 1H, CH), 7.83 (m, 1H,
CH), 7.92 (d, 1H, J ¼ 9.0 Hz, CH), 8.19 (d, 1H, J ¼ 6.0 Hz, 8.34
1
3
s, 1H, CH), 8.54 (s, 1H, NH); C NMR (75 MHz, DMSO-d6):
(
d ¼ 65.1, 114.6, 114.9, 117.5, 121.6, 122.7, 123.3, 125.9, 127.4, 131.3,
1
33.4, 133.6, 134.7, 144.3, 144.3, 147.3, 147.7, 163.3; MS (EI): m=e ¼ 269
þ
(
M ), 221, 147, 120, 92, 65, 39.
Compound 4b
ꢁ
1
IR (KBr, cm ): 1608, 1679, 3065, 3345, 3360 cm ; H-NMR (300 MHz,
ꢁ1
1
CDCl ): d ¼ 7.56 (t, J ¼ 6.0 Hz, 1H, CH), 7.86 (m, 3H, 2CH, 1NH), 8.16
3
1
3
(
(
1
1
d, J ¼ 6.0 Hz, 1H, CH), 8.39 (m, 5H, CH), 12.8 (s, 1H, NH); C NMR
75 MHz, DMSO-d6): d ¼ 65.5, 121.2, 123.6, 125.9, 127.7, 129.3, 134.8,
þ
38.6, 148.3, 149.0, 150.8, 162.1; MS (EI): m=e ¼ 269 (M ), 267, 221,
92, 119, 92, 76, 50.
Compound 4c
ꢁ
1
ꢁ1
1
IR (KBr, cm ): 1602, 1677, 2225, 3027, 3124, 3169 cm ; H NMR
300 MHz, CDCl ): d ¼ 5.84 (s, 1H, CH), 7.55 (t, J ¼ 6.0 Hz, CH), 7.76
(
3

3572
S. Rostamizadeh et al.
(
8
d, J ¼ 6.0 Hz, 1H, CH), 7.87 (m, 1H, CH), 8.02 (d, J ¼ 6.0 Hz, 2H, CH),
.16 (d, J ¼ 6.0 Hz, 1H, CH), 8.32 (d, J ¼ 6.0 Hz, 2H, CH), 12.7 (s, 1H,
1
3
NH); C NMR (75 MHz, DMSO-d6): d ¼ 65.5, 113.6, 118.3, 121.2,
1
25.9, 127.2, 127.7, 128.6, 132.5, 134.7, 136.9, 150.9, 162.1; MS (EI):
þ
m=e ¼ 249 (M ), 247, 119, 92, 50.
Compound 4d
ꢁ
1
1
; H NMR (300 MHz,
IR (KBr): 1663, 3039, 3178, 3281, 3409 cm
CDCl ): d 4.33 (s, 1H, NH), 5.11 (s, 2H, CH2), 5.69 (s, 1H, NH), 5.85
3
(
s, 1H, CH), 6.66 (d, 1H, J ¼ 7.9 Hz, CH), 6.68–6.93 (m, 1H,
J ¼ 7.4 Hz, CH), 7.0 (d, 2H, J ¼ 8.7 Hz, CH), 7.31–7. 5 (m, 6H, CH),
7
.51 (d, 2H, J ¼ 8.7 Hz, CH), 7.76 (d, 1H, J ¼ 7.7 Hz, CH); MS (EI):
þ
m=e ¼ 330 (M ), 329, 239, 147, 120, 91, 65.
Compound 4e
ꢁ
1
IR (KBr, cm ): 1653, 2926, 3055, 3193; 3306 cm ; H NMR (300 MHz,
ꢁ1
1
CDCl ): d 4.36 (s, 1H, NH), 5.88 (s, 1H, CH), 6.78 (s, 1H, NH), 6.67
3
(
d, 1H, J ¼ 7.9 Hz, CH), 6.92 (t, 1H, J ¼ 7.5 Hz, CH), 7.32 (t, 1H,
J ¼ 8.0 Hz, CH), 7.48 (d, 2H, J ¼ 8.4 Hz, CH), 7.58 (d, 2H, J ¼ 8.4 Hz,
1
3
CH), 7.93 (d, 1H, J ¼ 7.7 Hz, CH); C NMR (75 MHz, DMSO-d6):
d ¼ 65.7, 114.4, 114.9, 117.2, 121.5, 127.3, 129.0, 131.2, 133.3, 141,
þ
1
47.5, 163.4; MS (EI): m=z ¼ 303 (M ), 272, 147, 120, 92, 77, 65, 50.
Compound 4f
ꢁ
1
ꢁ1
1
IR (KBr, cm ): 1647, 2916, 3065, 3198, 3363 cm ; H NMR (300 MHz,
CDCl ): d ¼ 3.8 (s, 1H, NH), 4.79 (s, 1H, NH), 6.32 (s, 1H, CH), 6.65
3
(
3
d, 1H, J ¼ 7.8 Hz, CH), 6.85 (t, 1H, J ¼ 7.2 Hz, CH), 7.28–7.33 (m,
H, CH), 7.37–742 (m, 1H, CH), 7.69–7.73 (m, 1H, CH), 7.88 (d, 1H,
1
3
J ¼ 7.7 Hz, CH). C NMR (75 MHz, DMSO-d6): d ¼ 63, 114.5, 114.6,
1
(
17.4, 127.3, 127.4, 128.7, 129.5, 130.2, 133.4, 137.8, 147.6, 163.6; MS
þ
EI): m=e ¼ 258 (M ), 147, 120, 102, 92, 77, 65.
Compound 4g
ꢁ
1
ꢁ1
1
IR (KBr, cm ): 1647, 2962, 3075, 3245, 3291, 3352 cm ; H NMR
300 MHz, CDCl ): d ¼ 4.67 (s, 1H, NH), 5.95 (s, 1H, NH), 6.35 (s, 1H,
(
3
CH), 6.66 (d, 1H, J ¼ 8.0 Hz, CH), 6.89 (t, 1H, J ¼ 7.4 Hz, CH), 7.31–7.36

Synthesis of New Substituted 2,3-Dihydroquinazolinones
3573
(
m, 1H, CH), 7.50 (d, 1H, J ¼ 8.0 Hz, CH), 7.6 (d, 1H, J ¼ 7.8 Hz, CH),
1
3
7
1
1
.93 (d, 1H, J ¼ 7.8 Hz, CH); C NMR (75 MHz, DMSO-d6): d ¼ 64.2,
14.53, 114.57, 117.5, 127.1, 127.3, 128.3, 129.8, 130.0, 132, 133.5,
45.6, 147.3, 163.4; MS (EI): m=e ¼ 292 (M ), 273, 147, 120, 92, 65, 43.
þ
Compound 4h
ꢁ
1
ꢁ1
1
IR (KBr, cm ): 1668, 2947, 3039, 3101, 3137, 3178 cm ; H NMR
300 MHz, CDCl ): d ¼ 4.32 (s, 1H, NH), 5.73 (s, 1H, NH), 5.91 (s, 1H,
(
3
CH), 6.67 (d, J ¼ 8.0 Hz, 1H, CH), 6.29 (t, J ¼ 7.5 Hz, 1H, CH), 7.14
(
2
t, J ¼ 8.5 Hz, 2H, CH), 7.36 (t, J ¼ 7.4 Hz, 1H, CH), 7.6 (t, J ¼ 6.8 Hz,
þ
H, CH), 7.95 (d, J ¼ 7.8 Hz, 1H, CH); MS (EI): m=e ¼ 242 (M ), 240,
1
19, 92, 75, 63, 50.
Compound 4i
ꢁ
1
IR (KBr, cm ): 1484, 1511, 1611, 1660, 3310 cm ; H NMR (300 MHz,
ꢁ1
1
CDCl ): d 4.36 (s, 1H, NH), 5.85 (s, 1H, NH), 5.9 (s, 1H, CH), 6.67–6.69
3
(d, J ¼ 8.0 Hz, 1H, CH, Ph), 6.89–6.94 (t, J ¼ 7.46 Hz, 1H, CH), 7.32–7.38
(t, J ¼ 7.6 Hz, 1H, CH), 7.4–7.45 (d, J ¼ 8.4 Hz, 2H, CH), 7.45–7.56
(d, J ¼ 8.4 Hz, 2H, CH), 7.7–7.96 (d, J ¼ 7.8 Hz, 1H, CH).
ACKNOWLEDGMENT
The authors gratefully acknowledge the Research Council of K. N. Toosi
University of Technology for partial financial support of this work.
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