Synthesis and biological evaluation of new series…
CH3), 2.31–2.37 (m, 2H, CH2), 2.38 (s, 3H, CH3), 2.46–2.42 (m, 2H, CH2)
4.10–4.04 (q, J = 8.1 Hz, 2H, CH2), 5.07 (s, 1H, CH), 6.14 (s, 1H, NH), 6.93–6.94
(t, J = 2.7 Hz, 1H, H Ar), 7.12–7.09 (m, 3H, H Ar) ppm; 13C NMR (100 MHz,
CDCl3): dC = 14.20 (CH3), 19.41 (CH3), 21.02 (CH3), 21.57 (CH2), 27.48 (CH2),
36.28 (CH2), 37.05 (CH), 59.80 (OCH2), 106.1, 113.4, 125.0, 126.8, 127.8, 128.8,
137.2 (C Ar), 143.2 (C Ar), 147.0, 149.6, 167.5 (CO2), 195.7 (C=O) ppm; MS
m/z = 325 [M]? (33), 295 (16), 234 (100), 205 (77), 160 (16); Anal. Calcd. for
C19H21NO2: C, 73.84; H, 7.07; N, 4.30 %. Found: C, 73.67; H, 7.32; N, 3.71 %.
3-Acetyl-4-(2-hydroxy-5-bromophenyl)-2-methyl-4,6,7,8-tetrahydro-
1H-quinoline-5-one (6)
Yield 0.32 g (85 %); white powder; m.p.: 209–211 °C; IR (KBr, mmax/cm-1): 3420,
3281, 3088, 2951, 2900, 1714, 1580, 1511, 1472, 1378, 1237, 1195, 1027 cm-1; 1H
NMR spectrum (300 MHz, DMSO-d6): dH = 1.62–1.58 (m, 1H, CH2), 1.98–1.93
(d, J = 12.9 Hz, 1H, CH2), 2.03 (s, 3H, CH3), 2.23 (s, 3H, CH3), 2.40–2.30 (m, 2H,
CH2), 3.02 (s, 1H, NH), 4.42 (s, 1H, CH), 6.75-6.72 (d, J = 8.7 Hz, 1H, H Ar),
7.17–7.14 (d, J = 7.8 Hz, 1H, H Ar), 7.36 (s, 1H, H Ar), 7.68 (s, 1H, OH) ppm; 13
C
NMR (75 MHz, DMSO-d6): dC = 20.07 (CH3), 20.74 (CH3), 28.74 (CH2), 30.54
(CH2), 32.99 (CH2), 47.34 (CH), 84.45, 109.1, 111.4, 118.0, 129.4, 130.4 (C Ar),
131.0, 150.0, 150.7, 192.7 (C=O), 204.4 (C=O) ppm; MS m/z = 378 [M]? (50), 360
(66), 332 (31), 204 (100), 162 (53); Anal. Calcd. for C20H22BrNO: C, 57.6; H, 4.80;
N, 3.73 %. Found: C, 56.98; H, 4.83; N, 3.69 %.
A sample experimental procedure for the synthesis of ethyl-4-
(3-methylphenyl)-2-methyl-5-oxo-4,5-dihydro-1H-indeno-
[1,2-b]pyridine-3-carboxylate (7)
A mixture of ammonium acetate (0.077 g, 1 mmol), 3-methylbenzaldehyde
(0.120 g, 1 mmol), 1,3-indandione (0.146 g, 1 mmol), ethyl acetoacetate
(0.130 g, 1 mmol) and TCBDA (0.06 g, 0.16 mmol) or PCBS (0.05 g), ethanol
(2 mL) was stirred at room temperature for the appropriate time. The progress of the
reaction was monitored by TLC (9:3, n-hexane/acetone). After completion of the
reaction, ethanol (10 mL) was added. The crude product was filtered, washed with
ethanol and dried. The crude product was recrystallized from methanol to give the
pure product. Evaporation of the solvent was followed by the addition of CH2Cl2
(10 mL) recycling the catalysts. Yield 0.33 g (92 %); red powder; m.p.:
256–258 °C; IR (KBr, mmax/cm-1): 3436, 3274, 3192, 3083, 2984, 1670, 1637,
1512, 1189, 1085 cm-1 1H NMR spectrum (500 MHz, CDCl3): dH = 1.17 (t,
;
J = 7.0 Hz, 3H, CH3), 2.3 (s, 3H, CH3), 2.51 (s, 3H, CH3), 4.08 (q, 2H, CH2), 6.86
(s, 1H, NH), 6.96 (d, J = 3.5 Hz, 1H, H Ar), 7.15–7.11 (m, 4H, H Ar), 7.29 (s, 1H,
H Ar), 7.38–7.37 (d, J = 6.0 Hz, 2H, H Ar) ppm; 13C NMR (100 MHz, CDCl3):
dC = 14.01 (CH3), 19.66 (CH3), 21.47 (CH3), 37.24 (CH), 60.01 (OCH2), 108.2,
110.6, 117.1, 121.3, 125.0, 127.2, 128.0, 128.6, 130.0 (C Ar), 131.2, 134.0, 136.1,
137.5, 143.2 (C Ar), 145.6, 153.2, 167.4 (CO2), 192.4 (C=O) ppm; MS m/z = 359
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