Synthetic and Antimicrobial Studies of Quinolinylpyrimidines
J. Chin. Chem. Soc., Vol. 55, No. 2, 2008 399
m/z 398 (M+1, 65%). Anal. Calcd for C25H19NO4: (397.13):
C, 75.55; H, 4.82; N, 3.52. Found: C, 76.42; H, 4.68; N,
3.82.
ica gel column chromatography using ethyl acetate/n-hex-
ane (3:2) as eluent, mp 272-274 ºC, IR (KBr, nmax in cm-1):
3700-3440, 1615, 1587, 1552, 1H NMR (300 MHz, CDCl3)
d: d 8.05 (dd, J = 1.5, 7.5 Hz, 1H, H5), 7.67-7.54 (br-m, 3H,
H6, H7, H8), 7.41-7.20 (m 5H, protons of phenyl ring), 7.01
(m, 1H, methine proton), 3.35 (s, 3H, NCH3), 13C NMR
(75.5 MHz, CDCl3) d: 190.1 (CO), 164.1, 141.3, 137.2,
134.2, 132.8, 131.1, 129.2, 128.9, 127.8, 126.3, 124.5,
119.8, 113.7, 109.5, 28.4, Mass spectrum (ESI) m/z 368,
(M+23, 10%), 344 (M-1, 35%), 328 (M-OH, 100%). Anal.
Calcd for C20H15N3O3: (345.11): C, 69.56; H, 4.38; N,
12.17; O, 13.9. Found: C, 69.85; H, 4.26; N, 12.27.
3-[6-(4-Chlorophenyl)-1,2-dihydro-2-oxopyrimidin-4-
yl]-4-hydroxy-1-ethylquinolin-2(1H)-one (2-a)
The title compound (2-a) was prepared from 3-[(E)-
3-(4-chlorophenyl)acryloyl]-1-ethyl-4-hydroxyquinolin-
2(1H)-one (0.35 g, 1 mmol) and urea (0.06 g, 1 mmol) by
both methods and purified by column chromatography
with ethyl acetate/n-hexane (3:2) as eluent. M.p. 282-284
ºC, IR (KBr, nmax in cm-1): 3738-3450, 1663, 1632, 1594,
1533, 1H NMR (300 MHz, CDCl3) d: 8.24 (dd, J = 1.8, 7.8
Hz, 1H, H5), 7.88-7.50 (br-m, 3H, H6, H7, H8), 7.41-7.24 (br-
m, 4H, protons of p-chlorophenyl), 7.05 (m, 1H, methine
proton, 4.24 (q, J = 7.2 Hz, 2H, N-CH2CH3), 1.30 (t, J = 7.2
Hz, 3H, N-CH2CH3), 13C NMR (75.5 MHz, CDCl3) d:
194.9 (CO), 180.5, 168.9, 144.8, 138.2, 137.98, 135.86,
133.95, 133.59, 131.55, 129.5, 124.4, 118.07, 114.3, 18.6,
Mass spectrum (ESI) m/z 394 (M+1, 25%), 396 (M+1+2,
10%), 376 (M-OH, 25%). Anal. Calcd for C21H16ClN3O3:
(393.08): C, 64.05; H, 4.09; N, 10.67. Found: C, 63.85; H,
4.02; N, 10.23.
3-[6-(4-Chlorophenyl)-1,2-dihydro-2-thiopyrimidin-4-
yl]-4-hydroxy-1-phenylquinolin-2(1H)-one (2-d)
The title compound (2-d) was prepared from 3-[(E)-
3-(4-chlorophenyl)acryloyl]-4-hydroxy-1-phenylquino-
lin-2(1H)-one (0.40 g, 1 mmol) and thiourea (0.08 g, 1
mmol) by the above-described methods and purified by sil-
ica gel column chromatography with ethyl acetate/n-hex-
ane (4:1) as eluent. M.p. >300 ºC, IR (KBr, nmax in cm-1):
1
3664-3350, 1640, 1597.4, 1534.8, H NMR (300 MHz,
CDCl3) d: d 15.02 (s, 1H, OH), 8.92 (br-s, 1H, NH), 8.20
(d, J = 7.5 Hz, 1H, H5), 8.03 (d, J = 8.1 Hz, 2H, H6, H7),
7.62-7.38 (br-m, 6H, H8, 5H of N-Phenyl), 7.31-7.11 (m,
4H, p-chlorophenyl), 6.36 (s, 1H, methine proton), 13C
NMR (75.5 MHz, CDCl3) d: 186.4, 174.2, 148.3, 133.9,
130.2, 129.4, 128.2, 127.3, 126.9, 126.0, 125.1, 124.3,
122.2, 120.7, 119.1, 114.7, 114.3, Mass spectrum (ESI) m/z
456 (M-1, 100%), 458 (M+1, 33%). Anal. Calcd for
C25H16ClN3O2S: (457.06): C, 65.57; H, 3.52; N, 9.18.
Found: C, 65.25; H, 3.42; N, 8.95.
3-[6-(4-Chlorophenyl)-1,2-dihydro-2-oxopyrimidin-4-
yl]-4-hydroxy-1-methylquinolin-2(1H)-one (2-b)
The title compound (2-b) was prepared from 3-[(E)-
3-(4-chlorophenyl)acryloyl]-4-hydroxy-1-methylquino-
lin-2(1H)-one (0.34 g, 1 mmol) and urea (0.06 g, 1 mmol)
by the above-described methods and purified by column
chromatography with ethyl acetate/n-hexane (2:1) as
eluent. M.p. >300 ºC, IR (KBr, nmax in cm-1): 3724-3450,
1
1643, 1599.4, 1519.2, H NMR (300 MHz, CDCl3) d: d
8.04 (dd, J = 1.5, 7.8 Hz, 1H, H5), 7.65-7.56 (br-m, 3H, H6,
H7, H8), 7.45-7.17 (m, 4H, p-chlorophenyl), 7.03 (m, 1H,
methine proton), 3.32 (s, 3H, NCH3), 13C NMR (75.5 MHz,
CDCl3) d: 189.6, 174.9, 164.0, 141.3, 136.0, 133.7, 133.1,
132.5, 131.0, 129.4, 129.2, 126.3, 124.5, 119.7, 113.7,
109.4, 28.3, Mass spectrum (ESI) m/z 402 (M+23, 20%),
378 (M-1, 20%), 380 (M+1, 10%), 362 (M-OH, 100%).
Anal. Calcd for C20H14ClN3O3: (379.07): C, 63.25; H, 3.72;
N, 11.06. Found: C, 62.96; H, 3.64; N, 10.93.
3-[6-(4-Methoxyphenyl)-1,2-dihydro-2-thiopyrimidin-
4-yl]-4-hydroxy-1-phenylquinolin-2(1H)-one (2-e)
The title compound (2-e) was prepared from 4-hy-
droxy-3-[(E)-3-(4-methoxyphenyl)acryloyl]-1-phenyl-
quinolin-2(1H)-one (0.40 g, 1 mmol) and thiourea (0.08 g,
1 mmol) by the above-described methods and purified by
column chromatography with ethyl acetate/n-hexane (3:1)
as eluent. M.p. >300 °C, IR (KBr, nmax in cm-1): 3640-3250,
1645, 1600, 1550, 1H NMR (300 MHz, CDCl3) d: 15.02 (s,
1H, OH), 8.86 (br-s, 1H, NH), 8.41 (s, 1H, H5), 8.20 (t, J =
6.9 Hz, 1H, H-7), 8.02 (d, J = 8.7 Hz, 1H, H6), 7.96 (d, J =
8.7 Hz, 1H, H8), 7.61-7.42 (br-m, 5H, protons of N-phenyl
ring), 7.30-7.11 (m, 4H, protons of 4-methoxy phenyl), 6.3
(m, 1H, methine proton, 3.8 (s, 3H, -OCH3), 13C NMR
(75.5 MHz, CDCl3) d: 187.3, 174.2, 150.2, 135.3, 131.2,
3-[6-Phenyl-1,2-dihydro-2-oxopyrimidin-4-yl]-4-hy-
droxy-1-methylquinolin-2(1H)-one (2-c)
The title compound (2-c) was prepared from 4-hy-
droxy-3-[(E)-3-(4-methoxyphenyl)acryloyl]-1-methyl-
quinolin-2(1H)-one (0.34 g, 1 mmol) and urea (0.06 g, 1
mmol) by the above-described methods and purified by sil-