Synthesis and in vitro antibacterial activities of novel 2-aryl-3-(phenylamino)-2,3-dihydroquinazolin-4(1h)-one derivatives

Article abstract of DOI:10.1002/jhet.1075

An efficient synthesis of novel 2-aryl-3-(phenylamino)-2,3- dihydroquinazolin-4(1H)-one derivatives using KAl(SO₄) ₂.12H₂O (Alum) as a catalyst from an aldehyde and 2-amino-N-phenylbenzohydrazine in ethanol is described. A

Full text of DOI:10.1002/jhet.1075

Month 2013
Synthesis and In Vitro Antibacterial Activities of Novel 2-Aryl-3-
phenylamino)-2,3-dihydroquinazolin-4(1H)-one Derivatives
(
a
b
c
Ali A. Mohammadi, * Hamed Rohi, and Ali Abolhasani Soorki
a
Department of Chemistry, Sabzevar Branch, Islamic Azad University, Sabzevar, Iran
Faculty of Science, Department of Chemistry, Ferdosy University, Mashad, Iran
b
c
Shaheed Beheshti University, Academic Center for Education, Culture, and Research,
Research Institute of Applied Sciences, Tehran, Iran
*
E-mail: aliamohammadi@iaus.ac.ir
Received May 29, 2011
DOI 10.1002/jhet.1075
Published online 00 Month 2013 in Wiley Online Library (wileyonlinelibrary.com).
An efficient synthesis of novel 2-aryl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one derivatives
using KAl(SO ) .12H O (Alum) as a catalyst from an aldehyde and 2-amino-N-phenylbenzohydrazine in
4
2
2
ethanol is described. All synthesized derivatives were screened for anti-bacterial activity. Some compounds
exhibited promising anti-bacterial activity with reference to standard antibiotics.
J. Heterocyclic Chem., 00, 00 (2013).
INTRODUCTION
During recent years, the use of KAl(SO ) .12H O
Alum) compounds as catalysts or promoters in organic
synthesis has attracted great interest from many chemists
1–4]. Alum enhances the reactivity and selectivity of
RESULTS AND DISCUSSION
As per our ongoing work to synthesize privileged-class
bioactive nitrogen-containing heterocyclic compounds
[36–38], and in view of our interest in the KAl(SO4)
.12H O catalyzed reaction [39,40], we herein report a
4
2
2
(
[
2
2
many types of reactions such as carbon–carbon bond for-
mation [5], esterification [6], cycloaddition [7], acylation
convenient and rapid methodology for synthesis of some
new 2-aryl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-
one derivatives 5 in the presence of Alum as a non-toxic,
reusable, inexpensive and easily available reagent in ethanol
at reflux.
[8], and multicomponent condensations [9].
2
,3-Dihydroquinazolinone derivatives have drawn
much attention due to their broad range of pharmacologi-
cal activities such as antibiotic [10], antidefibrillatory
The initial aim of our work was to synthesize 2-amino-
N-phenylbenzohydrazide 3 followed by the reaction of
isatoic anhydride 1 with phenylhydrazine 2 in the pres-
ence of Alum using ethanol as a solvent at reflux. The
strategy for the synthesis of 2-aryl-3-(phenylamino)-2,3-
dihydroquinazolin-4(1H)-one derivatives 5 has been depicted
in Scheme 1. The synthetic methodology commenced with
the synthesis of 2-aminophenylbenzohydrazide 3. Subse-
quently, the 2-aryl-3-(phenylamino)-2,3-dihydroquinazolin-4
(1H)-one derivatives 5 was prepared by the reaction of 2-
aminophenylbenzohydrazide 3 with aldehydes 4, using alum
in ethanol at reflux, in excellent yield and purity (Scheme 1).
The completion of the reaction was monitored by TLC at
regular intervals, and the disappearance of the starting
material was observed within 5 h. The optimized results are
summarized in Table 1.
[
11], antispermatogenic [12], vasodilatory [13], and anal-
gesic [14] ability.
,3-Dihydroquinazolinone derivatives have been pre-
2
pared by the reaction of anthranilamides with aldehydes or
ketones under either acidic or basic conditions [15–19], by
the reductive desulfurization of 2-thioxo-3H-quinazolin-4-
ones with nickel boride in dry methanol [20], also by the
reductive cyclization of o-nitrobenzamides with aldehydes
or ketone using TiCl /Zn in an hydrous THF [21], or SnCl2
4
in alcohol [22], as well as by the reaction of isatoic anhy-
dride with Schiff bases [23–25]. Also, the reduction of
quinazolin-4(3H)-ones [26,27], as well as the one-pot reac-
tion of isatoic anhydride, a primary amine, and aromatic
aldehyde in the presence of silica sulfuric acid [28], mont-
morillonite K10 [29], ionic liquids [30], Ga(OTf) [31],
3
1
Zn(PFO)2 [32], I2 [33], and other routes have been
utilized for its synthesis [34,35]. However, none of the
The structures of products were characterized by IR, H
13
NMR, C NMR, MS spectra, and elemental analysis.
The new synthesized compounds were screened in vitro
for their antibacterial activities against of bacteria
Escherichia coli ATCC 25922, Pseudomonas aeruginusa
ATCC 85327, Klebsiella pneumonia, ATCC 29655
2
,3-dihydroquinazolinone compounds prepared by these
methods contains 3-phenylamino in 3 position. Here, we
report a new synthesis of 2,3-dihydroquinazolinone deriv-
atives with 3-phenyl amino group.
©
2013 HeteroCorporation

A. A. Mohammadi, H. Rohi, and A. A. Soorki
Vol 000
1
13
pellets on a Shimadzu IR-470 spectrophotometer. H and
C
(Gram-negative bacteria), Enterococcus faecalis ATCC
NMR spectra were determined on a Bruker 300 DRX Avance
instrument at 300 and 75 MHz. Elemental analysis for C, H,
and N were performed using a Heraus CHN rapid analyzer.
General experimental procedure for synthesis of 2-aryl-3-
2
1
9737, Bacillus subtilis ATCC 465, Bacillus pumilus PTCC
114, Micrococcus luteus PTCC 1110, Staphylococcus
aureus ATCC 25923, Staphylococcus epidermidis ATCC
2228, Sterptococcus mutans PTCC 1601 (Gram-positive
1
(phenylamino)-2,3-dihydroquinazolin-4(1H)-one 5a-j.
A
bacteria) by the disk diffusion method (IZ) [41], and subse-
quently the minimum inhibitory concentration (MIC) [42].
Activities of each compound were compared with tetra-
cycline and gentamicin as standards. MIC and IZ results
for bacterial strains are shown on Table 2. The screening
results indicate that some of the tested compounds exhibit
significant antibacterial activities when compared with the
reference drugs. It was observed that the compound
mixture of 1 mmol 3, 1 mmol aldehyde 4, 0.4 g Alum, and 5
mL EtOH in a 20-mL flask was stirred at reflux for periods
indicated in Table 1. After completion of the reaction
(
monitored by TLC, ethyl acetate/n-hexane, 1/1), EtOH was
removed under reduced pressure, 25 mL H O was added to the
2
reaction mixture, the resulting solid was separated by filtration,
and recrystallized from ethanol to afford pure product.
2
-Amino-N′-phenylbenzohydrazide (3).
White powder
(99)%; mp 170–172°C; IR (potassium bromide): 3428 (NH),
1
containing N(Me) substituted group in 4 position of 2-
3335 (NH), 3230 (NH), 1645 (C O); H NMR (DMSO-d ): δ
2
6
H
aryl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one 5f
shows better activity than the other test compounds and
the reference, tetracycline and gentamicin, drugs. Meanwhile,
6.39 (s, 2H, NH
2
2
), 6.56 (t, 1H, J = 7.8, ArH), 6.69–6.75 (m,
H, ArH), 6.78 (d, 2H, J = 7.7, ArH), 7.13–7.22 (m, 3H, ArH),
.66 (d, 1H, J = 7.8, ArH), 7.79 (s, 1H, NH), 10.10 (s, 1H,
7
13
NH);
C NMR (DMSO-d ): δC 112.75, 113.27, 115.19,
6
2
-aryl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one
1
16.86, 119.00, 128.45, 129.18, 132.65, 150.27, 150.34, 169.33.
-(4-Nitrophenyl)-3-(phenylamino)-2,3-dihydroquinazolin-
(1H)-one (5a). Cream powder (92)%; mp 220–222°C; IR
compounds 5e, 5f, 5h, 5i, 5j exhibited good activity, whine
the remaining compounds generally showed inferior activi-
ties against all the tested strains.
In summary, we have described a successful strategy, ef-
ficient and convenient green synthesis for the preparation
of 2-aryl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-
ones in valuing cyclocondensation reaction of aldehydes
and 2-amino-N-phenylbenzohydrazine using the inexpen-
2
4
1
(potassium bromide): 3374 (NH), 3238 (NH), 1660 (C O);
H
NMR (DMSO-d ): δ 6.09 (s, 1H, CH), 6.70–6.86 (m, 5H, ArH),
6
H
7.18 (t, 2H, J = 7.6, ArH), 7.30 (t, 1H, J = 7.7, ArH), 7.63 (d, 1H,
J = 7.7, ArH), 7.69 (d, 1H, J = 8.3, ArH), 7.76 (s, 1H, NH), 8.20
13
(
d, 2H, J = 8.3, ArH), 8.50 (s, 1H, NH); C NMR (DMSO-d
δC 73.22, 112.88, 114.61, 115.24, 118.34, 119.94, 124.02, 128.13,
29.24, 129.43, 134.51, 146.87, 147.92, 148.08, 148.45, 162.88;
6
):
1
+
sive, nontoxic and easily available KAl(SO ) .12H O
4
2
2
MS (70 eV, electron impact) m/z: 360 (M , 50), 312 (20), 268
(
Alum) catalyst. Surprisingly, compounds 5f and 5j with
(35), 237 (40), 206 (25), 178 (25), 120 (50), 91 (100), 77 (20), 65
(45), 51 (30), 39 (30); Anal. Calcd for C20H N O : C, 66.66; H,
16 4 3
the potencies similar to or better than those of tetracycline
and gentamicin against Escherichia coli ATCC 25922,
Pseudomonas aeruginusa ATCC 85327, Klebsiella
pneumonia, ATCC 29655 (Gram-negative bacteria),
Enterococcus faecalis ATCC 29737, Bacillus subtilis
ATCC 465, Bacillus pumilus PTCC 1114, Micrococcus
luteus PTCC 1110, Staphylococcus aureus ATCC 25923,
Staphylococcus epidermidis ATCC 12228, Sterptococcus
mutans PTCC 1601 (Gram-positive bacteria), worth further
investigations.
4
.48; N, 15.55; Found: C, 66.56; H, 4.37; N, 15.44.
,4-Dichlorophenyl)-3-(phenylamino)-2,3-dihydroquinazolin-
(1H)-one (5b). Cream powder (90)%; mp 196–198°C; IR
2
4
1
(
potassium bromide): 3365 (NH), 3258 (NH), 1656 (C O);
H
NMR (DMSO-d ): δ 6.24 (s, 1H, CH), 6.72–6.80 (m, 5H,
6
H
ArH), 7.15 (t, 2H, J = 7.7, ArH), 7.30 (t, 1H, J = 7.4, ArH),
7.43–7.49 (m, 2H, ArH), 7.52 (s, 1H, ArH), 7.66 (d, 1H, J = 6.4,
13
ArH), 7.70 (s, 1H, NH), 8.28 (s, 1H, NH); C NMR (DMSO-
d
1
1
2
6 C
): δ 71.03, 112.72, 114.05, 115.32, 118.31, 119.83, 128.06,
29.30, 129.40, 129.72, 133.51, 134.42, 134.54, 136.69, 146.51,
+
47.95, 163.21; MS (70 eV, electron impact) m/z: 308 (M , 50),
91 (50), 252 (35), 237 (40), 222 (25), 193 (25), 165 (30), 119
(
75), 106 (50), 90 (60), 77 (20), 65 (100), 51 (30), 39 (30); Anal.
EXPERIMENTAL
Calcd for C20 O: C, 62.51; H, 3.93; N, 10.94; Found:
2 3
H15 Cl N
General methods.
Melting points were obtained in open
C, 62.42; H, 4.01; N, 10.82.
capillary tubes and were measured on an electro-thermal 9200
apparatus. Mass spectra were recorded on a Shimadzu QP 1100
BX mass spectrometer. The IR spectra were recorded on KBr
2-(4-Bromophenyl)-3-(phenylamino)-2,3-dihydroquinazolin-
4(1H)-one (5c).
Cream powder (91)%; mp 178–180°C; IR
1
(potassium bromide): 3337 (NH), 3269 (NH), 1626 (C O);
H
Scheme 1
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2013
Synthesis and In Vitro Antibacterial Activities of Novel 2-Aryl-3-(phenylamino)-
2,3-dihydroquinazolin-4(1H)-one Derivatives
Table 1
The synthesis of 2‐aryl‐3‐(phenylamino)‐2,3‐dihydroquinazolin‐4(1H)‐one 5a–j.
a
Product
R
Time (h)
Yield (%)
m.p. (°C)
Lit. m.p. (°C)
5
5
5
5
5
5
5
5
5
5
a
b
c
d
e
f
g
h
i
p‐NO
2,4‐di‐ClC
p‐BrC
Ph
2
C
6
H
H
6 3
4
6
7
7
5
7
6
7
7
6
6
92
90
91
93
91
93
91
94
94
93
220–222
196–198
178–180
198–200
191–193
222–224
177–179
217–219
162–164
205–207
–
–
–
–
–
–
–
–
–
–
6
H
4
o‐HOC
6
H
4
p‐N(Me)
m‐NO
p‐MeOC
p‐MeC
p‐FC
2
C
6 4
H
2
C
6
H
4
4
6
H
6
H
4
j
6
H
4
a
Yields of pure isolated product based on isatoic anhydride.
NMR (DMSO-d
.16 (t, 2H, J = 7.5, ArH), 7.26 (t, 1H, J = 7.0, ArH), 7.40 (d, 2H,
J = 8.3, ArH), 7.53 (d, 2H, J = 8.4, ArH), 7.62 (d, 1H, J = 8.3,
6
): δ
H
5.91 (s, 1H, CH), 6.69–6.84 (m, 5H, ArH),
5.89 (s, 1H, CH), 6.68–6.80 (m, 3H, ArH), 6.84 (d, 2H, J = 7.7,
ArH), 7.17 (t, 2H, J = 7.4, ArH), 7.25–7.37 (m, 4H, ArH), 7.42
7
(d, 2H, J = 6.4, ArH), 7.63 (d, 1H, J = 7.3, ArH), 7.65 (s, 1H,
13
13
ArH), 7.64 (s, 1H, NH), 8.39 (s, 1H, NH); C NMR (DMSO-d6):
NH), 8.38 (s, 1H, NH); C NMR (DMSO-d ): δC 74.05,
6
δ
C
73.48, 112.84, 114.63, 115.13, 118.09, 119.79, 122.05, 128.06,
112.86, 114.71, 115.07, 117.86, 119.70, 126.84, 128.01,
129.13, 129.39, 131.69, 134.39, 140.52, 147.11, 148.19, 163.01;
128.79, 129.36, 134.26, 141.22, 147.31, 148.31, 163.06; MS
+
+
+
MS (70 eV, electron impact) m/z: 395 (M +2, 30), 393 (M , 30),
01 (35), 250 (20), 214 (100), 178 (45), 118 (50), 90 (80), 77
(70 eV, electron impact) m/z: 315 (M , 25), 242 (25), 210 (35),
3
118 (30), 91 (100), 77 (20), 63 (45), 51 (30), 39 (30); Anal.
Calcd for C H N O: C, 76.17; H, 5.43; N, 13.32; Found: C,
(60), 63 (45), 51 (65), 39 (60); Anal. Calcd for C H BrN O: C,
20
16
3
20 17 3
6
0.93; H, 4.09; N, 10.66; Found: C, 60.82; H, 4.02; N, 10.54.
-Phenyl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one
5d). Creampowder(93)%;mp198–200°C;IR(potassiumbromide):
76.22; H, 5.32; N, 13.21.
2
2-(2-Hydroxyphenyl)-3-(phenylamino)-2,3-dihydroquina-
zolin-4(1H)-one (5e). Cream powder (91)%; mp 191–193°C;
IR (potassium bromide): 3385 (OH), 3315 (NH), 3269 (NH),
(
3
1
311 (NH), 3250 (NH), 1648 (C O); H NMR (DMSO-d ): δ
6 H
Table 2
Antibiotic activity of the synthesized compounds and standard antibiotics against some gram positive and gram negative bacteria, as determined by disc
diffusion test (IZ) and minimum inhibitory concentration (MIC) methods.
Tetracycline
Gentamicin
(
30 μg/disc)
(10 μg/disc)
5a,b,c,d,g
MIC IZ
5e
5f
5i
MIC IZ
5j
5h
MIC
a
b
Microorganisms
IZ
MIC
IZ
0
MIC IZ
IZ MIC
512
10 256
NT
MIC IZ
41
MIC IZ
16 24
c
Bacillus subtilis
21
17
19
20
34
4
NT
0
0
0
0
0
NT
NT
NT
NT
NT
22
24
12
19
17
7
4
<2
<2
<2
<2
<2
18
20
14
15
15
<2
<2
4
(
ATCC 465)
Bacillus pumilus
PTCC 1114)
Micrococcus luteus
PTCC 1110)
Staphylococcus aureus
ATCC 25923)
8
0
NT
NT
NT
NT
<2 38
8
28
(
4
0
0
128 24
32 20
16 24
32 24
(
4
0
14 128
12 128
8
4
35
38
<2
4
(
Staphylococcus
epidermidis
<2
0
(
ATCC 12228)
Streptococcus mutans
PTCC 1601)
Escherichia coli
ATCC 25922)
Enterococcus faecalis
ATCC 29737)
Pseudomonas aeruginosa
ATCC 85327)
Klebsiella pneumonia
ATCC 29655)
24
0
2
NT
8
0
23
0
NT
4
0
0
0
0
0
NT
NT
NT
NT
NT
22
18
13
14
15
16
0
32
NT
NT
NT
NT
4
8
34
28
<2
<2
<2
<2
8
14
12
12
0
64 30
64 16
256 14
<2
8
(
(
9
NT
8
0
256 26
256 22
128 15
8
(
0
NT
16
12
0
0
NT
NT
0
0
NT
NT
(
8
NT
0
0
(
a
Inhibition zone (mm).
Minimum inhibitory concentration (μg/mL).
b
c
Not tested.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

A. A. Mohammadi, H. Rohi, and A. A. Soorki
Vol 000
1
1
6
634 (C O); H NMR (DMSO-d ): δ 6.08 (s, 1H, CH), 6.66–
117.80, 119.66, 126.77, 127.98, 129.29, 129.35, 134.20, 138.06,
138.25, 147.33, 147.33, 148.33, 163.12; MS (70 eV, electron
impact) m/z: 329 (M , 30), 237 (100), 207 (50), 178 (45), 120
6
H
.89 (m, 7H, ArH), 7.10–7.22 (m, 1H, NH, 4H, ArH), 7.67
d, 1H, J = 7.7, ArH), 8.29 (s, 1H, NH), 10.00 (s, 1H, OH);
C NMR (DMSO-d
15.92, 117.68, 119.11, 119.74, 126.58, 126.74, 127.86,
29.44, 129.77, 134.05, 147.19, 148.17, 155.14, 163.53; MS
70 eV, electron impact) m/z: 331 (M , 40), 236 (65), 221
40), 207 (35), 178 (40), 118 (50), 91 (100), 77 (55), 77 (60);
5 (45), 51 (30), 44 (30); Anal. Calcd for C20
2.49; H, 5.17; N, 12.68; Found: C, 72.38; H, 5.05; N, 12.74.
-(4-(Dimethylamino)phenyl)-3-(phenylamino)-2,3-dihydro-
quinazolin-4(1H)-one (5f). Cream powder (93)%; mp 222–
24°C; IR (potassium bromide): 3309 (NH), 3260 (NH), 1654
+
(
1
3
): δ
6 C
69.41, 112.73, 114.46, 115.33,
(60), 91 (90), 77 (60), 63 (45), 51 (20), 44 (35); 39 (60); Anal.
Calcd for C H N O: C, 76.57; H, 5.81; N, 12.76; Found: C,
1
1
(
(
6
7
21 19 3
76.50; H, 5.71; N, 12.65.
+
2-(4-Folorophenyl)-3-(phenylamino)-2,3-dihydroquinazolin-4
(1H)-one (5j).
Cream powder (93)%; mp 205–207°C; IR
1
17 3 2
H N O : C,
(potassium bromide): 3327 (NH), 3262 (NH), 1626 (C O); H
NMR (DMSO-d ): δ 5.92 (s, 1H, CH), 6.68–6.83 (m, 5H,
6
H
2
ArH), 7.13–7.20 (m, 4H, ArH), 7.26 (t, 1H, J = 7.0, ArH),
7.44–7.49 (m, 2H, ArH), 7.61 (m, 2H, NH and ArH), 8.36 (s,
1
3
2
(
1H, NH); C NMR (DMSO-d ): δC 73.45, 112.83, 114.61,
6
1
C O); H NMR (DMSO-d
6
): δ
H
2.84 (s, 6H, 2CH
3
), 5.76 (s,
115.10, 115.42, 115.70, 117.99, 119.71, 128.04, 128.97,
1
7
7
7
1
1
3
H, CH), 6.64–6.77 (m, 5H, ArH), 6.82 (d, 2H, J = 7.7, ArH),
.13–7.29 (m, 5H, ArH), 7.45 (s, 1H, NH), 7.61 (d, 1H, J =
129.09, 129.35, 134.34, 137.41, 147.22, 148.25, 163.03; MS
(70 eV, electron impact) m/z: 333 (M , 40), 241 (40), 178
+
1
3
.6, ArH), 8.23 (s, 1H, NH); C NMR (DMSO-d
6
): δ
C
40.70,
(40), 120 (65), 92 (65), 77 (100), 77 (100), 51 (30), 39 (30);
Anal. Calcd for C H FN O: C, 72.06; H, 4.84; N, 12.61;
4.00, 112.44, 114.83, 113.30, 114.72, 115.01, 117.62,
19.56, 127.63, 127.97, 129.32, 134.11, 147.55, 148.41,
2
0
16
3
Found: C, 72.10; H, 4.73; N, 12.54.
+
50.82, 163.23; MS (70 eV, electron impact) m/z: 358 (M , 20),
13 (20), 266 (35), 237 (55), 206 (25), 178 (20), 118 (95), 90
(
100), 77 (70), 65 (45), 51 (50), 39 (30); Anal. Calcd for
O: C, 73.72; H, 6.19; N, 15.63; Found: C, 73.63; H,
.08; N, 15.64.
-(3-Nitrophenyl)-3-(phenylamino)-2,3-dihydroquinazolin-4
1H)-one (5g). Cream powder (91)%; mp 177–179°C; IR
potassium bromide): 3301 (NH), 2352 (NH), 1652 (C O); H
): δ 6.14 (s, 1H, CH), 6.71–6.85 (m, 5H,
ArH), 7.71 (t, 2H, J = 8.1, ArH), 7.31 (t, 1H, J = 7.1, ArH),
Acknowledgments. We gratefully acknowledge the financial
support from the Research Council of Islamic Azad University,
Sabzevar Branch.
22 22 4
C H N
6
2
(
(
1
REFERENCES AND NOTES
NMR (DMSO-d
6
H
[1] Azizian, J.; Mohammadi, A. A.; Karimi, A. R.;
7
7
8
1
1
1
3
.66 (t, 2H, J = 7.8, ArH), 7.79 (s, 1H, ArH), 7.88 (d, 1H, J =
.6, ArH), 8.16 (d, 1H, J = 8.1, ArH), 8.32 (s, 1H, NH),
Mohammadizadeh, M. R.; Koohshari, M. Heterocycles 2004, 63, 2013.
[2] Mohammadi, A. A.; Azizian, J.; Hadadzahmatkesh, A.;
Asghariganjeh, M. R. Heterocycles 2008, 75, 947.
1
3
6 C
.54 (s, 1H, NH); C NMR (DMSO-d ): δ 73.14, 112.87,
[
3] Mohammadi, A. A,; Mivechi, M.; Kefayati, H. Monatsh Chem
008, 139, 935.
[4] Mohammadi, A. A.; Dabiri, M.; Qaraat, H. Tetrahedron 2009,
5, 3804.
5] Sonar, S. S.; Sadaphal, S. A.; Kategaonkar, A. H.; Pokalwar,
14.63, 115.27, 118.37, 119.89, 121.77, 123.80, 128.13,
2
6
29.41, 130.44, 133.53, 134.53, 143.37, 146.88, 148.10,
+
48.19, 162.96; MS (70 eV, electron impact) m/z: 360 (M ,
0), 268 (35), 237 (40), 206 (45), 178 (45), 120 (50), 91
[
(
100), 77 (40), 65 (35), 51 (30), 39 (30); Anal. Calcd for
: C, 66.66; H, 4.48; N, 15.55; Found: C, 66.53;
H, 4.39; N, 15.61.
-(4-Methoxyphenyl)-3-(phenylamino)-2,3-dihydroquinazolin-
(1H)-one (5h). Cream powder (94)%; Cream powder; mp
16–218°C; IR (potassium bromide): 3266 (NH), 3262 (NH),
R. U.; Shingate, B. B.; Shingare, M. S. Bull Kor Chem Soc 2009, 30, 825.
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20 16 4 3
C H N O
2
4
2
1
5
7
[
8] Shelke, K.; Sapkal, S.; Kategaonkar, A.; Shingate, B.;
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1
6 H 3
641 (C O); H NMR (DMSO-d ): δ 4.24 (s. 1H, OCH ),
[
.97 (s, 1H, CH), 6.72–6.86 (m, 5H, ArH), 7.14 (t, 2H, J =
.7, ArH), 7.23 (d, 1H, J = 8.4, ArH), 7.42 (d, 2H, J = 8.4,
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ArH), 7.53 (d, 2H, J = 7.8, ArH), 7.60 (s, 1H, ArH), 7.65
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1
3
(
s, 1H, NH), 8.37 (s, 1H, NH); C NMR (DMSO-d
6
): δ
C
6
1
1
0.12, 74.38, 111.94, 113.95, 114.18, 116.95, 118.96, 127.07,
27.18, 128.95, 129.65, 137.05, 138.12, 138.42, 146.93,
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47.63, 149.03, 164.09; MS (70 eV, electron impact) m/z: 345
+
(
(
M , 35), 237 (100), 208 (50), 177 (45), 120 (50), 92 (85), 77
65), 63 (55), 50 (25), 44 (35); 39 (65); Anal. Calcd for
[15] Ozaki, K.; Yamada, Y.; Oine, T.; Ishizuka, T.; Iwasawa, Y. J
C H N O : C, 73.03; H, 5.54; N, 12.17; Found: C, 73.10; H,
Med Chem 1985, 28, 568.
2
1 19 3 2
5
.46; N, 12.06.
-(Phenylamino)-2-p-tolyl-2,3-dihydroquinazolin-4(1H)-
one (5i). Cream powder (95)%; mp 162–164°C; IR
potassium bromide): 3269 (NH), 3264 (NH), 1640 (C O); H
NMR (DMSO-d ): δH 2.24 (s. 1H, CH ), 5.92 (s, 1H, CH),
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3
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1
[19] Rueping, M.; Antonchick, A. P.; Sugiono, E.; Grenader, K.
Angew Chem Int Ed 2009, 48, 908.
(
6
3
[20] Khurana, J. M.; Kukreja, G. J Heterocycl Chem 2003, 40, 677.
6
.71–6.84 (m, 5H, ArH), 7.16 (t, 2H, J = 7.8, ArH), 7.29 (d, 1H,
[21] Shi, D.; Rong, L.; Wang, J.; Zhuang, Q.; Wang, X.; Hu, H.
J = 8.5, ArH), 7.40 (d, 2H, J = 8.5, ArH), 7.56 (d, 2H, J = 78.5,
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ArH), 7.62 (s, 1H, ArH), 7.64 (s, 1H, NH), 8.39 (s, 1H, NH);
[
13
6 C
C NMR (DMSO-d ): δ 21.11, 73.88, 112.84, 114.75, 115.08,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2013
Synthesis and In Vitro Antibacterial Activities of Novel 2-Aryl-3-(phenylamino)-
,3-dihydroquinazolin-4(1H)-one Derivatives
2
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet