Synthesis and Antibacterial Activity of Novel (4-Fluorophenyl)(4-(naphthalen-2-yl)-6-aryl-2-thioxo-2,3-dihydropyrimidin-1(6H)-yl)methanone Derivatives

Article abstract of DOI:10.1002/jhet.3368

A novel series of (4-fluorophenyl)(4-(naphthalen-2-yl)-6-aryl-2-thioxo-2,3-dihydropyrimidin-1(6H)-yl)methanone derivatives were synthesized from reaction of 6-(naphthalen-2-yl)-4-aryl-3,4-dihydropyrimidine-2(1H)-thiones with 4-fluorobenzoylchloride in dic

Full text of DOI:10.1002/jhet.3368

Month 2018
Synthesis and Antibacterial Activity of Novel (4-Fluorophenyl)(4-
(naphthalen-2-yl)-6-aryl-2-thioxo-2,3-dihydropyrimidin-
1(6H)-yl)methanone Derivatives
a
a
Thuraka Sekhar, Pinnu Thriveni,
Mypati Hari Krishna,a Kolluri Ramesh,a Sk Md Jasmine,b and Uday Sankar Allamb
*
aDepartment of Chemistry, Vikrama Simhapuri University, Nellore 524320, India
bDepartment of Biotechnology, Vikrama Simhapuri University, Nellore 524320, India
*E-mail: thriveni.vsu1@gmail.com
Received May 24, 2018
DOI 10.1002/jhet.3368
Published online 00 Month 2018 in Wiley Online Library (wileyonlinelibrary.com).
A novel series of (4-fluorophenyl)(4-(naphthalen-2-yl)-6-aryl-2-thioxo-2,3-dihydropyrimidin-1(6H)-yl)
methanone derivatives were synthesized from reaction of 6-(naphthalen-2-yl)-4-aryl-3,4-
dihydropyrimidine-2(1H)-thiones with 4-fluorobenzoylchloride in dichloromethane in the presence of
triethylamine. The synthesized compounds were screened for antibacterial activity against Gram positive
bacteria, namely, Staphylococcus aureus ATCC25923 and Listeria monocytogenes MTCC657, and Gram
negative bacteria, namely, Escherichia coli ATCC25922 and Klebsiella pneumoniae ATCC700603, respec-
tively. Some of the tested compounds showed significant antimicrobial activity.
J. Heterocyclic Chem., 00, 00 (2018).
INTRODUCTION
Pyrimidine-based organic materials represent
were obtained in a two-step synthesis. The one-pot, three-
component reaction of aryl ketones 1, aryl aldehydes 2, and
thiourea 3 in the presence of sodium methoxide is processed
rapidly in ethanol at 70°C to afford 6-(naphthalen-2-yl)-
4-aryl-3,4-dihydropyrimidine-2(1H)-thiones 4 in good yield.
The product 5, that is, (4-fluorophenyl)(4-(naphthalen-2-yl)-
6-aryl-2-thioxo-2,3-dihydropyrimidin-1(6H)-yl)methanone
derivatives, was synthesized by the reaction of 4 with 4-
fluorobenzoyl chloride in the presence of triethylamine in
dichloromethane as solvent at 0–5°C (Table 1, entries 5a-l).
The synthetic sequence is depicted in Scheme 1.
a
significant class of compounds, which acquired special
attention in heterocyclic chemistry. Pyrimidine occupies
an important position in the field of medicinal chemistry
due to a variety of pharmacological and biological activity
of its derivatives. On one hand, pyrimidine and its
derivatives possess significant antibacterial, antifungal,
anthelmintic, anticancer, and antitumor activity [1–9].
Pyrimidine is another important nitrogen containing
heterocycles, which has various drug-related properties
and have attracted extensive investigation for small
molecule drug discovery [10–13]. On the other hand,
pyrimidines also show versatile pesticidal activity as
herbicides [14,15]. Comparatively, there is much less
literature about the application of pyrimidine-containing
compounds in agrochemical area than in medicinal area
[16,17]. Naphthalene-substituted thiopyrimidine were
reported to contain antibacterial activity. In view of these,
we aimed the synthesis and bioassay of some novel
The structures of the compounds were elucidated by
spectral data. The infrared (IR) spectra of the
thiopyrimidine compounds (5a–5l) displayed absorption
bands for NH (3309–3220 cmÀ1), C═O (1692–
1662 cmÀ1), and SH (2351–2349 cmÀ1) functional
1
groups. The H NMR (400 MHz in DMSO-d6) spectrum
of compounds (5a–5l) displayed two doublets at 5.79–5.9
and 5.98–6.50 ppm for C─H pyrimidine protons. Apart
from these, 5a–5l also showed signals at 8.54–11.72 ppm
for NH pyrimidine proton. The signals of the other
protons were appeared at the expected chemical shifts
and integral values [19]. The structures of the compounds
were further confirmed by 13C NMR and mass spectra.
pyrimidine-2[1H]-thione derivatives with
a naphthyl
group, fluorobenzoyl group, and with aryl (electron
donating and electron withdrawing groups) as substituents
[18]. The antimicrobial activities of these target
compounds were evaluated and reported in this paper.
BIOLOGICAL ASSAY
RESULTS AND DISCUSSION
Methodology. Antibacterial activity of the synthesized
heterocyclic compounds was carried out using disk
diffusion method against two Gram positive bacteria
(Staphylococcus aureus ATCC25923 and Listeria
New derivatives of (4-fluorophenyl)(4-(naphthalen-2-yl)-
6-aryl-2-thioxo-2,3-dihydropyrimidin-1(6H)-yl)methanone
© 2018 Wiley Periodicals, Inc.

T. Sekhar, P. Thriveni, M. Hari Krishna, K. Ramesh, S. M. Jasmine, and U. S. Allam
Vol 000
Table 1
mL), the culture was swabbed onto the Mueller–Hinton
agar media. The plates were left for 5–10 min for
drying the excess swabbed culture. The dried filter
paper disks were impregnated onto the culture plate not
less than 24 mm from center to center. After gentle
pressing of the disks onto the culture, the plates were
incubated for about 24 h at 37°C. Streptomycin sulfate
(30 μg/mL) was used as a positive control and DMF
(30 μL) alone as negative control. Each of the test
compounds was tested in duplicates.
Synthesis of (4-fluorophenyl)(4-(naphthalen-2-yl)-6-aryl-2-thioxo-2,3-
dihydropyrimidin-1(6H)-yl)methanone derivatives.a
Compound
Ar
Yield %b
5a
5b
5c
5d
5e
5f
5g
5h
5i
3,4-Dimethoxyphenyl
4-Chlorophenyl
3-Bromophenyl
1-Naphthyl
3,4,5-Trimethoxyphenyl
Phenyl
4-Fluorophenyl
3,4-Dichlorophenyl
4-Methylphenyl
4-Methoxyphenyl
2-Chlorophenyl
2,6-Dichlorophenyl
81
80
82
79
83
75
78
82
77
81
77
78
Results. The results of heterocyclic compounds 5a–5l
are summarized in Table 2. The width of the zone of
inhibition represents the potency of the synthesized
compounds. The results revealed that majority of the
synthesized compounds showed varying degrees of
inhibition against the tested microorganisms. A strong
inhibition was shown by the compounds 5g and 5h at a
concentration of 400 μg/mL against Gram negative
bacteria, while 5f and 5l found to have high rates of
inhibition against Gram positive bacteria at the same
concentration with zone of inhibition 15–20 mm. The
synthesized heterocyclic compounds 5f, 5g, 5h, 5j, 5k,
and 5l displayed mild and moderate activity at 200 and
300 μg/mL against both Gram positive and Gram
negative organisms. However, no antibacterial activity
was observed at a concentration of 100 μg/mL against all
the tested organisms. Compound 5d is the only
heterocyclic molecule that has no antibacterial activity
against any species at any concentration. DMF served as
negative control with no zone of inhibition, and
streptomycin sulfate as positive control proved to be an
efficient drug against the organisms with a wider zone of
inhibition. Thus, in 13 synthesized heterocyclic
compounds, the aryl group with chloro and fluorophenyl
derivatives were more active.
5j
5k
5l
aReaction of 4 with 4-fluorobenzoyl chloride in the presence of
triethylamine in dichloromethane at 0°C.
bIsolated yield.
monocytogenes MTCC657) and two Gram negative
bacteria (Escherichia coli ATCC25922 and Klebsiella
pneumoniae ATCC700603). The bacterial culture media
Luria–Bertani broth, Mueller–Hinton agar, solvent
dimethylformamide (DMF), and antibiotic streptomycin
sulfate were purchased from HiMedia, Mumbai.
Antibacterial activity assay. Dimethylformamide was
used as solvent to dissolve the test compounds. A stock
concentration of 10 mg/mL was prepared with each of
the test compounds. Sterile filter paper disks of about
6 mm are impregnated with four different working
concentrations of the test solution from 100 to
400 μg/mL and air dried.
A single colony was
inoculated into 5 mL of the Luria–Bertani broth and
incubated at 37°C for 8–10 h. After adjusting the
turbidity to 0.5 Mac Farland standard (1.5 × 108 CFU/
Scheme 1. Synthetic scheme of (4-fluorophenyl)(4-(naphthalen-2-yl)-6-aryl-2-thioxo-2,3-dihydropyrimidin-1(6H)-yl)methanone derivatives.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2018
Synthesis and Antibacterial Activity of Novel (4-Fluorophenyl)(4-(naphthalen-2-
yl)-6-aryl-2-thioxo-2,3-dihydropyrimidin-1(6H)-yl)methanone Derivatives
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

T. Sekhar, P. Thriveni, M. Hari Krishna, K. Ramesh, S. M. Jasmine, and U. S. Allam
Vol 000
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2018
Synthesis and Antibacterial Activity of Novel (4-Fluorophenyl)(4-(naphthalen-2-
yl)-6-aryl-2-thioxo-2,3-dihydropyrimidin-1(6H)-yl)methanone Derivatives
Table 2
Antibacterial activity of compounds 5a–5l.
Escherichia coli
Klebsiella pneumoniae
Staphylococcus aureus
Listeria monocytogenes
S. no.
Compound
A
B
C
D
A
B
C
D
A
B
C
D
A
B
C
D
1
2
3
4
5
6
7
8
5a
5b
5c
5d
5e
5f
5g
5h
5i
À
À
À
À
À
À
À
À
À
À
À
À
À
À
À
À
À
+
À
+
À
++
+
À
À
À
À
À
À
À
À
À
À
À
À
À
À
À
À
À
+
À
À
À
À
À
À
À
+
++
À
+
++
+
+
À
++
++
À
À
À
À
À
À
À
À
À
À
À
À
À
À
À
À
À
À
+
+
++
++
À
++
++
++
À
À
À
À
À
À
À
À
À
À
À
À
À
À
À
À
À
+
+
+
+ +
+ +
+ +
À
À
++
À
À
À
À
++
++
++
++
À
++
++
+++
+++
À
++
++
+++
+++
À
+
++
+
+ +
+ + +
+ +
+ +
À
++
++
++
+
+
+
+++
++
++
++
++
++
+
++
+
À
+
+
+
++
À
9
À
À
À
À
À
+
+
À
10
11
12
13
14
5j
5k
5l
+
+
++
++
À
+
++
++
À
+
+
+ +
+ +
+ + +
+
À
++
+ + +
À
À
+
À
À
À
+
++
+++
À
Positive (30 μg/mL)
Negative (DMF)
+++
+++
+++
À
À
À
DMF, dimethylformamide.
A = 100 μg/mL, B = 200 μg/mL, C = 300 μg/mL, D = 400 μg/mL.
No antibacterial activity (À): inhibition zone 0–5 mm; mild sensitivity (+): inhibition zone 5–10 mm; moderate sensitivity (++): inhibition zone 10–
15 mm; highly sensitive (+++): inhibition zone 15–20 mm.
CONCLUSION
mL round bottom flask, and sodium methoxide was added
to the reaction mixture at room temperature. Then, the
resulting mixture was heated to 70°C and stirred for
20 min. The progress of the reaction was monitored by
TLC. After completion of the reaction, the reaction
mixture was allowed at room temperature and diluted
with 25 mL water. The compound was filtered and
recrystallized from toluene to afford desired product
6-(naphthalene-2-yl)-4-aryl-3,4-dihydropyrimidine-2(1H)-
thione derivatives 4.
In summary, we have synthesized
a series of
(4-fluorophenyl)(4-(naphthalen-2-yl)-6-aryl-2-thioxo-2,3-
dihydropyrimidin-1(6H)-yl)methanone derivatives, and
their antibacterial activities have been evaluated. All the
compounds are confirmed by their spectral data and
showed potent inhibition against all the tested strains.
EXPERIMENTAL
General procedure for the synthesis of (4-fluorophenyl)(4-
(naphthalen-2-yl)-6-aryl-2-thioxo-2,3-dihydropyrimidin-
1(6H)-yl)methanone derivatives (5a–5l). To 50-mL round
All the chemicals were purchased from Merck (Merck
Ltd, Mumbai, Maharshtra, India) and Sigma-Aldrich
(Bangloore, Karntaka, India). All the reactions were
performed and monitored by thin-layer chromatography
(TLC) on Merck silica gel 60 F254 pre-coated plates
(0.25 mm) and visualized by ultraviolet fluorescence
lamp. IR spectra were recorded on Bruker 683(FT)-IR
spectrometer (Bruker Corporation, Billerica, MA) with
KBr pellets. 1H NMR and 13C NMR spectra are
recorded on Bruker and Jiol Resonance (400 MHz) and
(100 MHz) spectrometer respectively, using DMSO-d6
or CDCl3 as a solvent and TMS as an internal
standard. Chemical shifts are reported in parts per
million (ppm). Mass spectra are scanned on Agilent
technologies spectrometer (Agilent Technologies, Santa
Clara, CA).
bottom flask, compound 4 (8 mmol) dissolved in 25 mL
of dichloromethane, and triethylamine (8 mmol) was
added, and the reaction mixture was cooled to 0°C. 4-
Fluorobenzoylchloride (8 mmol) was added to reaction
mixture over a period of 10 min at 0°C and stirred for
30 min at the same temperature. The progress of the
reaction was monitored by TLC. After completion of the
reaction, solvent was evaporated under reduced pressure
to get solid. The solid was taken into 20 mL water and
stirred for 10 min and filtered. The solid was
recrystallized from toluene.
(6-(3,4-Dimethoxyphenyl)-4-(naphthalen-2-yl)-2-thioxo-2,3-
dihydropyrimidin-1(6H)-yl)(4-fluorophenyl)methanone (5a).
mp: 244°C; IR (KBr) cmÀ1: 3232 (NH), 2350 (SH), 1662
1
(C═O), 1598 (C═C); H NMR (400 MHz, CDCl3-d6): δ
General procedure for the synthesis of 6-(naphthalene-2-yl)-
4-aryl-3,4-dihydropyrimidine-2(1H)-thione derivatives (4).
Aryl ketone 1 (8 mmol), aryl aldehyde 2 (8 mmol), and
thiourea 3 (8 mmol) in 25 mL ethanol were mixed in 50-
(ppm) 3.88 (3H, s, OCH3), 3.9 (3H, s, OCH3), 5.92 (1H,
d, J = 6.0 Hz, C─H), 6.10 (1H, d, J = 6.0 Hz, C─H),
6.86 (1H, d, J = 8.8 Hz Ar─H), 7.07–7.14 (3H, m,
Ar─H), 7.28 (1H, s, Ar─H), 7.58–7.67 (3H, m, Ar─H),
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

T. Sekhar, P. Thriveni, M. Hari Krishna, K. Ramesh, S. M. Jasmine, and U. S. Allam
Vol 000
7.74–7.78 (2H, m, Ar─H), 7.89–7.96 (4H, m, Ar─H),
(4-Fluorophenyl)(4-(naphthalen-2-yl)-6-phenyl-2-thioxo-
8.65 (1H, bs, NH); MS (m/z): 497.1 [M À 1]+.
(6-(4-Chlorophenyl)-4-(naphthalen-2-yl)-2-thioxo-2,3-
dihydropyrimidin-1(6H)-yl)(4-fluorophenyl)methanone (5b).
2,3-dihydropyrimidin-1(6H)-yl)methanone (5f). mp: 240°C;
1H NMR (400 MHz, DMSO-d6): δ (ppm) 5.93 (1H, d,
J = 6.6 Hz, C─H), 6.54 (1H, d, J = 6.7 Hz, C─H), 7.31
(3H, d, J = 8.9 Hz, Ar─H), 7.42 (2H, t, J = 7.3 Hz,
Ar─H), 7.63–7.51 (5H, m, Ar─H), 7.77–7.68 (2H, m,
Ar─H), 7.79 (1H, d, J = 8.5 Hz, Ar─H), 8.00 (2H, d,
J = 9.3 Hz, Ar─H), 8.24 (1H, s, Ar─H), 11.65 (1H, bs,
NH); 13C NMR (100 MHz, DMSO-d6): δ (ppm) 56.79,
108.55, 115.88, 116.10, 125.91, 126.91, 127.29, 127.42,
128.17, 128.74, 128.90, 129.10, 130.06, 132.00, 131.76,
133.00, 133.64, 136.07, 140.76, 163.28, 165.76, 172.28,
mp: 233°C; 1H NMR (400 MHz, DMSO-d6): δ (ppm) 5.94
(1H, d, J = 5.8 Hz, C─H), 6.52 (1H, d, J = 5.9 Hz, C─H),
7.28 (4H, d, J = 9.3 Hz, Ar─H), 7.58 (4H, s, Ar─H), 7.72
(2H, s, Ar─H), 7.80 (1H, d, J = 8.3 Hz, Ar─H), 7.98 (3H,
m, Ar─H), 8.25 (1H, s, Ar─H), 11.73 (1H, bs, NH); MS
(m/z): 471.1 [M À 1]+.
(6-(3-Bromophenyl)-4-(naphthalen-2-yl)-2-thioxo-2,3-
dihydropyrimidin-1(6H)-yl)(4-fluorophenyl)methanone (5c).
mp: 240°C; 1H NMR (400 MHz, DMSO-d6): δ (ppm)
5.94 (1H, d, J = 6.3 Hz, C─H), 6.54 (1H, d, J = 6.8 Hz,
C─H), 7.26–7.36 (4H, m, Ar─H), 7.42–7.54 (4H, m,
Ar─H), 7.68–7.94 (3H, m, Ar─H), 7.95–7.97 (3H, m,
Ar─H), 8.19 (1H, s, Ar─H), 11.77 (1H, bs, NH); 13C
NMR (100 MHz, DMSO-d6): δ (ppm) 56.16, 122.14,
124.40, 125.89, 125.98, 127.31, 127.47, 128.11, 128.78,
128.93, 129.55, 131.11, 131.40, 131.88, 133.06, 163.37,
+
179.14; MS (m/z): 439.13 [M + 1] .
(4-Fluorophenyl)(6-(4-fluorophenyl)-4-(naphthalen-2-yl)-2-
thioxo-2,3-dihydropyrimidin-1(6H)-yl)methanone (5g).
mp:
225°C; 13C NMR (100 MHz, DMSO-d6): δ (ppm) 56.06,
108.29, 115.90, 116.03, 124.30, 125.81, 127.52, 127.90,
127.31, 128.76, 128.01, 129.12, 129.20, 131.20, 131.80,
132.91, 133.80, 136.60, 160.98, 163.31, 163.40, 165.18,
172.28, 178.99; HRMS: (m/z) Anal. Calcd for
165.86, 172.30, 179.00; MS (m/z): 516.9 [MÀ1]+.
C27H19F2N2OS [M + H]+, 457.12; Found, 457.1175.
(6-(3,4-Dichlorophenyl)-4-(naphthalen-2-yl)-2-thioxo-2,3-
dihydropyrimidin-1(6H)-yl)(4-fluorophenyl)methanone (5h).
(4-Fluorophenyl)(6-(naphthalen-1-yl)-4-(naphthalen-2-yl)-2-
thioxo-2,3-dihydropyrimidin-1(6H)-yl)methanone (5d).
mp:
1
mp: 249°C; IR (KBr) cmÀ1: 3242 (N─H), 2350 (S─H),
247°C; H NMR (400 MHz, DMSO-d6): δ (ppm) 6.53
(1H, d, J = 6.5 Hz, C─H), 6.65 (1H, d, J = 6.3 Hz,
C─H), 7.38 (2H, d, J = 8.3 Hz, Ar─H), 7.48–7.58 (3H,
m, Ar─H), 7.62 (1H, dd, J = 12.8 Hz, J = 8. Hz, Ar─H),
7.70 (2H, d, J = 6.0 Hz Ar─H), 7.74–7.81 (2H, m,
Ar─H), 7.91 (3H, m, J = 7.9 Hz Ar─H), 7.97 (1H, d,
J = 5.7 Hz Ar─H), 8.02 (2H, d, J = 8. Hz Ar─H), 8.13
(1H, s, Ar─H), 8.46 (1H, d, J = 8.3 Hz Ar─H), 11.73
(1H, bs, NH); 13C NMR (100 MHz, DMSO-d6): δ (ppm)
56.07, 108.04, 115.95, 116.17, 122.82, 124.18, 124.27,
125.76, 126.16, 126.60, 127.25, 127.38, 128.05, 128.46,
128.69, 128.88, 129.30, 129.42, 129.97, 131.77, 131.87,
133.03, 133.56, 134.20, 135.58, 137.52, 163.36, 165.85,
172.48, 179.72; HRMS: (m/z) Anal. Calcd for
1
1663 (C═O), 1594 (C═C); H NMR (400 MHz, CDCl3):
δ (ppm) 6.07 (1H, d, J = 6.4 Hz, C─H), 6.26 (1H, d,
J = 6 Hz, C─H), 7.11 (2H, t, J = 8.8 Hz, Ar─H),
7.30–7.32 (1H, m, Ar─H), 7.32–7,37 (1H, m, Ar─H),
7.46–7.58 (6H, m, Ar─H), 7.78–7.93 (3H, m, Ar─H),
8.108–8.12 (1H, m, Ar─H), 8.69 (1H, s, NH); MS (m/z):
505 [M À 1]+.
(4-Fluorophenyl)(4-(naphthalen-2-yl)-2-thioxo-6-p-tolyl-2,3-
dihydropyrimidin-1(6H)-yl)methanone (5i). mp: 229°C; IR
(KBr) cmÀ1: 3233 (N─H), 2350.11(S─H), 1656 (C═O),
1
1495 (C═C); H NMR (400 MHz, CDCl3): δ (ppm) 2.36
(3H, s, CH3), 5.95 (1H, d, J = 6.4 Hz, C─H), 6.12 (1H,
d, J = 6.4 Hz, C─H), 7.07–7.11 (1H, m, Ar─H), 7.19–
7.28 (3H, m, Ar─H), 7.46 (1H, d, J = 8 Hz, Ar─H),
7.58–7.59 (2H, m, Ar─H), 7.59–7.66 (3H, m, Ar─H),
7.74–7.77 (2H, m, Ar─H), 7.90–7.93 (2H, m, Ar─H),
7.95–8.02 (1H, m, Ar─H), 8.54 (1H, s, NH); MS (m/z):
C31H21FN2OS [M + H]+, 488.14; Found, 488.1427.
(4-Fluorophenyl)(4-(naphthalen-2-yl)-2-thioxo-6-(3,4,5-
trimethoxyphenyl)-2,3-dihydropyrimidin-1(6H)-yl)methanone
(5e). mp: 240°C; IR (KBr) cmÀ1: 3220 (NH), 2351(SH),
1665 (C═O), 1592 (C═C); 1H NMR (400 MHz,
DMSO-d6): δ (ppm) 3.61–3.76 (9H, s, 3 × OCH3), 6.45
(1H, d, J = 6.1 Hz, C─H), 6.54 (1H, d, J = 6.0 Hz,
C─H), 6.99 (1H, s, Ar─H), 7.28 (2H, dd, J = 17.8 Hz,
J = 8.9 Hz, Ar─H), 7.40 (1H, s, Ar─H), 7.55 (3H, d,
J = 21.0 Hz Ar─H), 7.69 (1H, d, J = 25.0 Hz Ar─H),
7.82 (2H, dd, J = 19.3, J = 11 Hz Ar─H), 8.02 (2H, d,
J = 8.7 Hz Ar─H), 8.22 (1H, s, Ar─H), 11.72 (1H, bs,
NH); 13C NMR (100 MHz, DMSO-d6): δ (ppm) 56.47,
57.23, 60.52, 60.57, 104.06, 105.10, 108.77, 115.86,
116.09, 125.83, 127.40, 128.10, 128.74, 128.88, 153.47,
153.67, 170.16, 171.28, 172.19, 179.49, 179.76; HRMS:
(m/z) Anal. Calcd for C30H25FN2O4S [M + H]+, 528.15;
Found, 528.1587.
451 [M À 1]+.
(4-Fluorophenyl)(6-(4-methoxyphenyl)-4-(naphthalen-2-yl)-
2-thioxo-2,3-dihydropyrimidin-1(6H)-yl)methanone (5j). mp:
235°C; 1H NMR (400 MHz, CDCl3): δ (ppm) 3.81 (3H, s,
OCH3), 5.95 (1H, d, J = 6.0 Hz, C─H), 6.08 (1H, d,
J = 6.0 Hz, C─H), 6.91 (2H, d, J = 8.8 Hz, Ar─H),
7.11–7.28 (2H, m, Ar─H), 7.48 (2H, d, J = 8.8 Hz,
Ar─H), 7.58–7.59 (2H, m, Ar─H), 7.59–7.60 (1H, m,
Ar─H), 7.64–7.64 (2H, m, Ar─H), 7.73–7.91 (3H, m,
Ar─H), 7.92–8.03 (1H, m, Ar─H), 8.60 (1H, s, NH);
MS (m/z): 467.1 [M À 1]+.
(6-(2-Chlorophenyl)-4-(naphthalen-2-yl)-2-thioxo-2,3-
dihydropyrimidin-1(6H)-yl)(4-fluorophenyl)methanone (5k).
1
mp: 236°C; H NMR (400 MHz, CDCl3): δ (ppm) 6.16
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2018
Synthesis and Antibacterial Activity of Novel (4-Fluorophenyl)(4-(naphthalen-2-
yl)-6-aryl-2-thioxo-2,3-dihydropyrimidin-1(6H)-yl)methanone Derivatives
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Pyrimidines; Wiley: New York, USA, 1994; Vol 52.
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Boulton, A. J.; McKillop, A. Eds.; Pergamon: Oxford, UK, 1984; Vol 3,
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[16] Panner Selvam, T.; Caido Richa, J.; Phadte Vijaysarathy, D.;
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Article ID 202784.
(1H, d, J = 6.0 Hz, C─H), 6.37 (1H, d, J = 6.4 Hz, C─H),
7.12–7.46 (5H, m, Ar─H), 7.55–7.64 (4H, m, Ar─H),
7.80–7.88 (4H, m, Ar─H), 7.81–8.21 (2H, m, Ar─H),
8.76 (1H, s, NH); MS (m/z): 473.09 [M + 1] .
(6-(2,6-Dichlorophenyl)-4-(naphthalen-2-yl)-2-thioxo-2,3-
+
dihydropyrimidin-1(6H)-yl)(4-fluorophenyl)methanone (5l).
mp: 240°C; IR (KBr) cmÀ1: 3309 (N─H), 2349 (S─H),
1692 (C═O), 1585 (C═C); 1H NMR (400 MHz,
DMSO-d6): δ (ppm) 5.70 (1H, d, J = 4.1 Hz, C─H), 6.65
(1H, d, J = 4.2 Hz, C─H), 7.23–7.34 (2H, m, Ar─H),
7.36 (1H, d, J = 8.5 Hz, Ar─H), 7.49 (2H, d, J = 7.9 Hz,
Ar─H), 7.52–7.58 (2H, m, Ar─H), 7.72 (1H, d,
J = 8.6 Hz, Ar─H), 7.95 (5H, m, Ar─H), 8.24 (1H, s,
Ar─H), 11.17 (1H, bs, NH); 13C NMR (100 MHz,
DMSO-d6): δ (ppm) 46.09, 57.33, 100.68, 116.12,
116.34, 124.32, 125.69, 127.17, 127.34, 128.03, 128.53,
128.89, 130.31, 130.21, 131.09, 132.49, 132.58, 133.60,
135.37, 136.06, 163.91, 166.41, 172.43, 177.32; HRMS:
(m/z) Anal. Calcd for C27H27Cl2FN2OS [M + H]+,
507.05; Found, 507.0489.
[18] Mahammed, S.; Makki, T.; Reda, M.; Abdel, R. Hindavi J
Chem 2013 Article ID 819462.
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Acknowledgments. Dr. P.Thriveni would like thank to IICT,
Hyderabad, S.V. University, Tirupati and V.S. University,
1
Nellore for providing us facilities of IR Spectra, H NMR, 13C
NMR and Mass spectras.
SUPPORTING INFORMATION
REFERENCES AND NOTES
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Additional supporting information may be found online
in the Supporting Information section at the end of the
article.
[3] Ritaand, E.; Shrivasthav, S. P. Eur J Chem 2010, 7, 935.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet