FAAL HAMEDANI ET AL.
7
3
.2.5 | 2‐(4‐Nitrophenyl)‐4H‐pyrido[2,1‐a]
CDCl
3
): 13.8 (Me), 62.3 (CH
2
O), 103.4 (CH), 118.2 (CH),
isoquinolin‐4‐one (5e)
119.7 (CH), 122.4 (CH), 130.2 (C), 131.5 (CH), 132.3 (CH),
34.6 (CH), 135.2 (CH), 136.2 (C), 144.3 (C), 151.3 (C),
1
+
Pale yellow powder, mp 168°C to 170°C, yield: 0.52 g
160.2 (C=O), 168.4 (C=O) ppm. MS, m/z (%): 267 (M ,
10), 222 (86), 129 (100), 45 (100). Anal. Calcd. for
C H NO (267.28): C 71.90, H 4.90, N 5.24; Found: C
−
1
(83%). IR (KBr) (ν /cm ): 1742, 1698, 1675, 1589,
max
−
1 1
1
487, 1295 cm . H NMR (500 MHz, CDCl ): 6.57 (1H,
3
16 13
3
3
s, CH), 6.84 (1H, s, CH), 7.12 (1H, d, J = 7.6 Hz, CH),
72.05, H 5.02, N 5.39.
3
3
7
.25 (1H, t, J = 7.6 Hz, CH), 7.46 (1H, t, J = 7.6 Hz,
3
3
CH), 7.65 (2H, d, J = 7.8 Hz, 2 CH), 7.72 (1H, d, J =
3
3.3.2 | 1‐(4‐Methoxyphenyl)‐1H‐pyrido[1,2‐
a]quinolin‐4‐one (9b)
7
.6 Hz, CH), 7.85 (1H, d, J = 7.6 Hz, CH), 8.42 (2H, d,
3
3
J = 7.8 Hz, 2 CH), 8.92 (1H, d, J = 7.6 Hz, CH) ppm.
1
3
C NMR (125.7 MHz, CDCl ): 110.5 (CH), 111.6 (CH),
3
Yellow powder, mp 115°C to 117°C, yield: 0.42 g (70%). IR
1
12.8 (CH), 116.4 (CH), 123.7 (2 CH), 125.2 (CH), 126.8
−
1
(
KBr) (ν /cm ): 1738, 1697, 1643, 1578, 1446, 1284
max
−
(CH), 127.4 (CH), 128.4 (CH), 131.5 (C), 132.4 (2 CH),
1 1
cm . H NMR (500 MHz, CDCl ): 3.83 (3H, s, MeO),
3
1
1
1
7
39.4 (C), 143.2 (C), 145.2 (C), 147.3 (C), 148.4 (C),
75.2 (C=O) ppm. MS, m/z (%): 316 (M , 20), 187 (62),
29 (100). Anal. Calcd. for C H N O (350.21): C
2.15, H 3.82, N 8.86; Found: C 72.32, H 3.96, N 8.95.
3
3
+
6.85 (2H, d, J = 7.6 Hz, 2 CH), 6.94 (1H, d, J = 7.6 Hz,
CH), 7.02 (1H, s, CH), 7.15 (1H, d, J = 7.6 Hz, CH), 7.22
3
19
12 2 2
3
3
(
1H, d, J = 7.6 Hz, CH), 7.34 (2H, d, J = 7.6 Hz, 2 CH),
3
7
.38 (1H, s, CH), 7.47 (1H, t, J = 7.6 Hz, CH), 7.65 (1H,
3
3
d, J = 7.6 Hz, CH), 7.95 (1H, d, J = 7.6 Hz, CH) ppm.
13
3.3 | General procedure for preparation of
C NMR (125.7 MHz, CDCl ): 55.7 (MeO), 107.6 (CH),
3
compound 9
112.3 (2 CH), 115.3 (CH), 118.4 (CH), 123.4 (CH), 127.8 (2
CH), 130.4 (C), 131.6 (CH), 132.2 (C), 133.4 (CH), 134.5
To a stirred mixture of 2‐aminobenzaldehyde 7 (2
mmol) and acetaldehyde 8 (2 mmol) on solvent‐free
conditions, after 30 minutes, methyl malonyl chloride
(
(
CH), 135.4 (CH), 143.4 (C), 144.5 (C), 149.5 (C), 160.4
C=O), 172.2 (C=O) ppm. MS, m/z (%): 301 (M , 15), 172
+
(
62), 129 (100). Anal. Calcd. for C H NO (301.34): C
20
15
2
3
8
(2 mmol) and water (3 mL) as solvent were added at
0°C. In other pot, alkyl bromide and
79.72, H 5.02, N 4.65; Found: C 79.85, H 5.18, N 4.78.
4
triphenylphosphine 5 were mixed in the presence of
Fe O ‐MNPs (10 mol%) at 80°C on solvent‐free condi-
3.3.3 | 1‐(4‐Methylphenyl)‐1H‐pyrido[1,2‐
a]quinolin‐4‐one (9c)
3
4
tion for 45 minutes. After this time, mixture of the sec-
ond pot was added to the first pot and let to be stirred
for 30 minutes. After completion of the reaction (4 h;
TLC control [hexane: AcOEt, 5:1]), the solution of
sodium hydroxide (10 mol%) was added to final mixture
at 80°C, and mixture was stirred for 2 hours. After com-
pletion of the reaction (2 h; TLC control [hexane:
AcOEt, 9:1]), the Fe O MNPs were separated by exter-
Yellow powder, mp 121°C to 123°C, yield: 0.41 g (72%). IR
−
1
(
KBr) (ν /cm ): 1742, 1698, 1656, 1584, 1468, 1352
max
−
1 1
cm . H NMR (500 MHz, CDCl ): 2.34 (3H, s, Me), 6.87
1H, s, CH), 6.97 (1H, d, J = 7.6 Hz, CH), 7.08 (1H, d, J
7.6 Hz, CH), 7.16 (1H, t, J = 7.6 Hz, CH), 7.27 (2H, d,
J = 7.6 Hz, 2 CH), 7.32 (1H, s, CH), 7.42 (1H, t, J = 7.6
Hz, CH), 7.53 (2H, d, J = 7.6 Hz, 2 CH),7.65 (1H, d, J =
.8 Hz, CH), 8.04 (1H, d, J = 7.6 Hz, CH) ppm. C NMR
3
3
3
(
3
=
3
3
3
4
3
3
nal magnet. After removing solvent, the residue was
purified by column chromatography (9:1, hexane:
EtOAc) to afforded pure title compounds.
3
13
7
(
125.7 MHz, CDCl ): 21.3 (Me), 107.2 (CH), 115.4 (CH),
3
118.5 (CH), 122.4 (CH), 128.2 (2 CH), 129.5 (2 CH), 130.2
(
(
C), 131.4 (CH), 132.2 (CH), 133.6 (CH), 134.5 (CH), 136.3
3
.3.1 | Ethyl 1‐oxo‐1H‐pyrido[1,2‐a]quino-
C), 138.2 (C), 141.2 (C), 144.3 (C), 149.7 (C), 161.2 (C=O)
+
line‐3‐carboxylate (9a)
ppm. MS, m/z (%): 301 (M , 15), 172 (84), 129 (100). Anal.
Calcd. for C H NO (301.34): C 79.72, H 5.02, N 4.65;
Found: C 79.87, H 5.16, N 4.76.
20
15
2
Yellow powder, mp 100°C 102°C, yield: 0.46 g (75%). IR
−
1
(
KBr) (ν /cm ): 1742, 1737, 1695, 1585, 1474, 1295
max
−
1
1
3
cm . H NMR (500 MHz, CDCl ): 1.16 (3H, t, J = 7.4
Hz, Me), 4.32 (2H, q, J = 7.4 Hz, CH O), 9.65 (1H, d, J
3
3
3
2
3.4 | 1,1‐Diphenyl‐2‐picrylhydrazyl radical
trapping test
3
=
7.5 Hz, CH), 7.12 (1H, d, J = 7.6 Hz, CH), 7.25 (1H, t,
J = 7.6 Hz, CH), 7.35 (1H, t, J = 7.6 Hz, CH), 7.42 (1H,
3
3
3
s, CH), 7.75 (1H, d, J = 7.6 Hz, CH), 7.86 (1H, s, CH),
Radical trapping activity of 6a, 6c, 9b, and 9c was calcu-
lated by DPPH (2, 2‐diphenyl‐1‐picrylhydrazyl) radical
3
13
8
.02 (1H, d, J = 7.5 Hz, CH) ppm. C NMR (125.7 MHz,