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R. B. Toche et al.
J = 6.6 Hz, 3 9 CH2), 3.45 (s, 3H, NCH3), 3.70 (s, 3H,
OCH3), 3.85–3.90 (t, 4H, J = 6.4 Hz, 2 9 CH2), 6.89–
7.25 (m, 4H, quinolone), 7.50 (d, 2H, J = 7.9 Hz, ArH),
7.96 (d, 2H, J = 7.9 Hz, ArH), 8.80 (s, 1H, pyridine),
12.60 (bs, 1H, OH) ppm.
(s, 3H, NCH3), 4.10 (s, 3H, OCH3), 7.02–7.44 (m, 4H,
quinolone), 7.64 (d, 2H, J = 8.2 Hz, ArH), 8.22 (d, 2H,
J = 8.2 Hz, ArH), 9.02 (s, 1H, pyridine), 13.50 (bs, 1H,
OH) ppm.
6-(1,2-Dihydro-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-4-
(3,4-dimethoxyphenyl)-2-(piperazin-1-yl)pyridine-3-carbo-
nitrile (4d, C28H27N5O4)
6-(1,2-Dihydro-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-4-
(3,4-dimethoxyphenyl)-2-(piperidin-1-yl)pyridine-3-carbo-
nitrile (3d, C29H28N4O4)
Yield 2.44 g (75%); m.p.: 176–178 °C; IR (KBr):
-1
ꢀ
Yield 1.90 g (66%); m.p.: 202–203 °C; IR (KBr):
m = 3,540 (OH), 2,245 (CN), 1,672 (CO), 1,556 cm ;
m = 3,404 (OH), 2,924 (CH), 2,204 (CN), 1,660 (CO),
1H NMR (300 MHz, DMSO-d6): d = 1.90–2.20 (t, 4H,
J = 6.9 Hz, 2 9 CH2), 2.30–2.45 (t, 4H, J = 6.9 Hz,
2 9 CH2), 3.60 (s, 3H, NCH3), 4.10–4.30 (s, 6H,
2 9 OCH3), 6.99–7.40 (m, 4H, quinolone), 7.60–7.88 (m,
3H, ArH), 8.90 (s, 1H, pyridine), 14.57 (bs, 1H, OH) ppm.
ꢀ
1
1,599, 1,575, 1,238 cm-1; H NMR (300 MHz, DMSO-
d6): d = 2.10–2.15 (t, 6H, J = 6.7 Hz, 3 9 CH2), 3.25–
3.64 (t, 2H, 2 9 CH2), 3.58 (s, 3H, NCH3), 3.64–3.85
(s, 6H, 2 9 OCH3), 6.80–7.20 (m, 4H, quinolone), 7.53
(d, 1H, J = 8.3 Hz, ArH), 7.45 (dd, J = 8.3, 2.1 Hz, 1H,
ArH), 7.80 (d, J = 2.1 Hz, 1H, ArH), 8.22 (s, 1H,
pyridine) ppm; 13C NMR (75 MHz, CDCl3): d = 29.0,
36.2, 40.1, 55.5, 55.5, 58.4, 109.0, 111.1, 111.7, 111.9,
112.1, 112.7, 114.9, 119.3, 119.8, 122.1, 122.1, 131.5,
136.8, 138.5, 147.7, 148.3, 149.9, 162.4 ppm; MS: m/z
(%) = 497 (M ? 1, 100), 456 (22), 395 (10).
4-(4-Chlorophenyl)-6-(1,2-dihydro-4-hydroxy-1-methyl-2-
oxoquinolin-3-yl)-2-(2-methyl-5-oxopyrrolidin-1-yl)pyri-
dine-3-carbonitrile (5a, C27H21ClN4O3)
Yield 2.66 g (66%); m.p.: 202–204 °C; IR (KBr):
ꢀ
m = 3,447 (OH), 2,218 (CN), 1,645 (CO), 1,630 (CO),
1,545 cm-1 1H NMR (300 MHz, DMSO-d6): d = 1.30
;
(s, 3H, CH3), 3.12 (t, 2H, CH2), 3.40–3.81 (t, 3H,
J = 6.4 Hz, CH2, CH), 4.02 (s, 3H, NCH3), 7.28-7.83
(m, 4H, quinolone), 7.94 (d, 2H, J = 8.2 Hz, ArH), 8.16
(d, 2H, J = 8.2 Hz, ArH), 8.68 (s, 1H, pyridine), 15.97 (bs,
1H, OH) ppm; 13C NMR (75 MHz, CDCl3): d = 14.5,
22.4, 28.7, 30.2, 32.4, 64.4, 101.4, 114.4, 122.5, 124.5,
126.7, 128.7 (s), 129.5 (s), 134.5, 139.7, 140.5, 159.8,
165.4, 170.4 ppm.
4-(4-Chlorophenyl)-6-(1,2-dihydro-4-hydroxy-1-methyl-2-
oxoquinolin-3-yl)-2-(piperazin-1-yl)pyridine-3-carbonitrile
(4a, C26H22ClN5O2)
Yield 1.66 g (60%); m.p.: 186–188 °C; IR (KBr):
-1
;
ꢀ
m = 3,480 (OH), 2,240 (CN), 1,680 (CO), 1,540 cm
1H NMR (300 MHz, DMSO-d6): d = 2.04–3.10 (t, 8H,
J = 6.6 Hz, 4 9 CH2), 3.88 (s, 3H, NCH3), 6.88–7.22 (m,
4H, quinolone), 7.35 (d, 2H, J = 8.1 Hz, ArH), 8.12 (d,
2H, J = 8.1 Hz, ArH), 8.44 (s, 1H, pyridine), 12.15 (bs,
1H, OH) ppm; 13C NMR (75 MHz, CDCl3): d = 20.2,
21.4, 30.2, 30.7, 55.4, 99.8, 128.2 (s), 132.8 (s), 138.2,
141.4, 148.2, 149.4, 150.2, 157.4, 160.1, 1700.4 ppm; MS:
m/z (%) = 473 (M ? 2), 471 (M?, 100).
4-(4-Bromophenyl)-6-(1,2-dihydro-4-hydroxy-1-methyl-2-
oxoquinolin-3-yl)-2-(2-methyl-5-oxopyrrolidin-1-yl)pyri-
dine-3-carbonitrile (5b, C27H21BrN4O3)
Yield 2.88 g (68%); m.p.: 205–206 °C; IR (KBr):
ꢀ
m = 3,087 (OH), 2,942 (CH), 2,227 (CN), 1,656 (CO),
1,644 (CO), 1,595, 1,570, 1,540 cm-1 1H NMR
;
4-(4-Bromophenyl)-6-(1,2-dihydro-4-hydroxy-1-methyl-2-
oxoquinolin-3-yl)-2-(piperazin-1-yl)pyridine-3-carbonitrile
(4b, C26H22BrN5O2)
(300 MHz, DMSO-d6): d = 1.45 (s, 3H, CH3), 2.87
(t, 2H, CH2), 3.20–3.60 (t, 3H, J = 6.4 Hz, CH2, CH),
3.90 (s, 3H, NCH3), 7.12–7.54 (m, 4H, quinolone), 7.60 (d,
2H, J = 8.6 Hz, ArH), 8.10 (d, 2H, J = 8.6 Hz, ArH),
8.74 (s, 1H, pyridine), 15.44 (bs, 1H, OH) ppm.
Yield 2.02 g (68%); m.p.: 212–213 °C; IR (KBr):
-1
;
ꢀ
m = 3,501 (OH), 2,218 (CN), 1,674 (CO), 1,544 cm
1H NMR (300 MHz, DMSO-d6): d = 1.90–2.90 (t, 8H,
J = 6.1 Hz, 4 9 CH2), 3.66 (s, 3H, NCH3), 6.90–7.35 (m,
4H, quinolone), 7.45 (d, 2H, J = 8.1 Hz, ArH), 8.20 (d,
2H, J = 8.1 Hz, ArH), 8.60 (s, 1H, pyridine), 12.60 (bs,
1H, OH) ppm.
6-(1,2-Dihydro-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-4-
(4-methoxyphenyl)-2-(2-methyl-5-oxopyrrolidin-1-yl)pyri-
dine-3-carbonitrile (5c, C28H24N4O4)
Yield 2.90 g (70%); m.p.: 188–190 °C; IR (KBr):
ꢀ
m = 3,119 (OH), 2,970 (CH), 2,216 (CN), 1,667 (CO),
6-(1,2-Dihydro-4-hydroxy-1-methyl-2-oxoquinolin-3-yl)-4-
(4-methoxyphenyl)-2-(piperazin-1-yl)pyridine-3-carboni-
trile (4c, C27H25N5O3)
1,654 (CO), 1,602, 1,585 cm-1 1H NMR (300 MHz,
;
DMSO-d6): d = 1.40 (s, 3H, CH3), 2.56 (t, 2H, CH2),
2.90–3.23 (t, 3H, J = 7.2 Hz, CH2, CH), 3.65 (s, 3H,
NCH3), 3.80 (s, 3H, OCH3), 6.98–7.22 (m, 4H, quinolone),
7.46 (d, 2H, J = 7.8 Hz, ArH), 7.92 (d, 2H, J = 7.8 Hz,
ArH), 8.55 (s, 1H, pyridine), 14.45 (bs, 1H, OH) ppm; 13C
NMR (75 MHz, DMSO-d6): d = 39.2, 45.7, 47.3, 65.5,
Yield 2.12 g (71%); m.p.: 222–223 °C; IR (KBr):
ꢀm = 3,404 (OH), 2,924 (CH), 2,204 (CN), 1,660 (CO),
1
1,599, 1,575, 1,238 cm-1; H NMR (300 MHz, DMSO-
d6): d = 1.80–2.40 (t, 8H, J = 6.7 Hz, 4 9 CH2), 3.45
123