K. K. Park, J. J. Lee / Tetrahedron 60 (2004) 2993–2999
2997
C17H17NO2: C, 76.38; H, 6.41; N, 5.24. Found: C, 76.22; H,
6.56; N, 5.14.
161.71, 150.73, 140.12, 136.90, 130.51, 128.76, 128.52,
128.40, 127.55, 121.77, 121.08, 120.32, 114.32, 29.45. IR
(KBr): nCvO 1665 cm21
.
4.3. General procedure for the synthesis of 4-phenyl-
quinolin-2(1H)-ones 2a-c
4.4.2. Compound 3b. Rf 0.46 (hexane–ethyl acetate, 2:1);
mp 99–100 8C (lit.11c 98–99 8C); 1H NMR d 7.59–7.39 (m,
8H), 7.14 (t, 1H, J¼8 Hz), 6.67 (s, 1H), 4.43 (q, 2H,
J¼7 Hz), 1.42 (t, 3H, J¼7 Hz); 13C NMR d 161.27, 150.69,
139.10, 137.02, 130.47, 128.75, 128.49, 128.41, 127.80,
121.56, 121.21, 120.62, 114.21, 37.26, 12.80. IR (KBr):
The mixture of N-acyl-o-aminobenzophenones 1a-c
(0.84 mmol) and sodium hydride (121 mg, 5.04 mmol) in
THF (4 ml) was heated at reflux for 2.5 h for 1a, 9 h for 1b,
and 20 h for 1c. Dichloromethane was added to the
concentrated reaction mixture and washed with distilled
water. The organic layer was dried over sodium sulfate,
filtered, and concentrated. Silica gel column chromato-
graphy of the residue (eluent: hexane–ethyl acetate, 2:1 for
2a; hexane–ethyl acetate, 3:1 for 2b; hexane–ethyl acetate,
5:1 and then 2:1 for 2c) provided the corresponding 2a-c in
83, 62, and 65% yields, together with the deacylated
compound, o-aminobenzophenone with 16, 23, and 22%
yields, respectively.
nCvO 1648 cm21
.
4.4.3. Compound 3c. Rf 0.84 (hexane–ethyl acetate, 2:1);
1
oil; H NMR d 7.59–7.39 (m, 8H), 7.14 (t, 1H, J¼8 Hz),
6.66 (s, 1H), 4.34 (t, 2H, J¼8 Hz), 1.80 (quintet, 2H,
J¼8 Hz), 1.50 (quintet, 2H, J¼7 Hz), 1.43–1.24 (m, 8H),
0.89 (t, 3H, J¼7 Hz); 13C NMR d 161.43, 150.60, 139.32,
137.02, 130.37, 128.74, 128.45, 128.38, 127.73, 121.49,
121.19, 120.57, 114.35, 42.34, 31.79, 29.36, 29.22, 27.54,
27.07, 22.63, 14.10. IR (KBr): nCvO 1652 cm21. Anal.
Calcd for C23H27NO: C, 82.84; H, 8.16; N, 4.20. Found: C,
82.87; H, 8.28; N, 4.32.
4.3.1. Compound 2a. Rf 0.10 (hexane–ethyl acetate, 2:1);
mp 259–261 8C (lit.16a 260 8C; lit.12b 260–262 8C; lit.15
257–259 8C); 1H NMR d 12.87 (s, 1H), 7.58–7.45 (m, 8H),
7.16 (t, 1H, J¼7 Hz), 6.71 (s, 1H); 13C NMR d 164.16,
153.33, 138.87, 137.05, 130.61, 128.78, 128.72, 128.53,
126.64, 122.46, 120.69, 119.52, 116.66. IR (KBr): nCvO
4.4.4. Compound 3d. Rf 0.31 (hexane–ethyl acetate, 2:1);
1
mp 132–133 8C; H NMR d 7.53–7.42 (m, 4H), 7.39 (d,
1H, J¼8 Hz), 7.23–7.19 (m, 2H), 7.12–7.05 (m, 2H), 3.82
(s, 3H), 2.03 (s, 3H); 13C NMR d 162.50, 146.49, 138.47,
136.92, 129.17, 128.77, 128.53, 127.78, 127.54 (two
overlapped C’s), 121.63, 121.56, 113.75, 29.95, 15.33. IR
(KBr): nCvO 1636 cm21. Anal. Calcd for C17H15NO:
C, 81.90; H, 6.06; N, 5.62. Found: C, 81.98; H, 6.05; N,
5.58.
1663 cm21
.
4.3.2. Compound 2b. Rf 0.13 (hexane–ethyl acetate, 2:1);
1
mp 227–228 8C (lit13 227–230 8C); H NMR d 12.61 (s,
1H), 7.55–7.41 (m, 5H), 7.27–7.24 (m, 2H), 7.09–7.03 (m,
2H), 2.10 (s, 3H); 13C NMR d 164.46, 148.68, 137.02,
136.90, 129.17, 128.70, 128.57, 127.86, 127.37, 126.63,
122.07, 121.02, 115.85, 14.38. IR (KBr): nCvO 1652 cm21
.
4.4.5. Compound 3e. Rf 0.44 (hexane–ethyl acetate, 2:1);
1
mp 111 8C (lit. 107–109 8C25); H NMR d 7.53–7.39 (m,
4.3.3. Compound 2c. Rf 0.28 (hexane–ethyl acetate, 2:1);
1
mp 166–168 8C; H NMR d 12.47 (s, 1H), 7.53–7.39 (m,
5H), 7.23–7.19 (m, 2H), 7.11 (dd, 1H, J¼8, 2 Hz), 7.06 (t,
1H, J¼8 Hz), 4.47 (q, 2H, J¼7 Hz), 2.02 (s, 3H), 1.43 (t,
3H, J¼7 Hz); 13C NMR d 161.95, 146.47, 137.42, 137.03,
129.13, 128.74, 128.53, 127.78, 127.73, 127.54, 121.83,
121.39, 113.64, 37.77, 15.20, 12.80. IR (KBr): nCvO
5H), 7.28–7.22 (m, 2H), 7.07–6.98 (m, 2H), 2.49 (t, 2H,
J¼8 Hz), 1.54 (quintet, 2H, J¼7 Hz), 1.28–1.17 (m, 4H),
0.83 (t, 3H, J¼7 Hz); 13C NMR d 164.08, 148.50, 137.06,
136.70, 132.12, 129.11, 128.72, 128.37, 127.77, 126.82,
121.96, 121.27, 115.67, 31.97, 28.83, 28.19, 22.31, 14.00.
IR (KBr): nCvO 1652 cm21. Anal. Calcd for C20H21NO: C,
82.44; H, 7.26; N, 4.81. Found: C, 82.72; H, 7.30; N, 5.04.
1629 cm21
.
4.4.6. Compound 3f. Rf 0.54 (hexane–ethyl acetate, 2:1);
mp 78–79 8C; 1H NMR d 7.52–7.43 (m, 4H), 7.37 (d, 1H,
J¼8 Hz), 7.22 (d, 2H, J¼8 Hz), 7.09–7.01 (m, 2H), 3.81 (s,
3H), 2.41 (t, 2H, J¼8 Hz), 1.46 (quintet, 2H, J¼8 Hz),
1.23–1.12 (m, 4H), 0.79 (t, 3H, J¼7 Hz); 13C NMR d
162.05, 146.42, 138.53, 136.73, 132.16, 129.17, 128.77,
128.35, 127.72 (two overlapped C’s), 121.78, 121.56,
113.69, 32.06, 29.86, 29.18, 28.79, 22.27, 13.98. IR
(KBr): nCvO 1647 cm21. Anal. Calcd for C21H23NO: C,
82.58; H, 7.59; N, 4.59. Found: C, 82.65; H, 7.64; N, 4.69.
4.4. General procedure for the synthesis of N-alkyl-4-
phenylquinolin-2(1H)-one derivatives 3a-g
The mixture of N-acyl-o-aminobenzophenones 1a-c
(0.84 mmol), alkyl iodide (2.10 mmol), and sodium hydride
(121 mg, 5.04 mmol) in THF (4 ml) was heated at reflux.
After the reaction, dichloromethane was added to the
concentrated reaction mixture and washed with distilled
water. The organic layer was dried over sodium sulfate,
filtered, and evaporated to afford a residue. Silica gel
column chromatography (eluent: hexane–ethyl acetate,
5:1 for 3c and n-hexane–ethyl acetate, 2:1 for others)
provided 3a-g. The yields and reaction times are listed in
Table 3.
4.4.7. Compound 3g. Rf 0.66 (hexane–ethyl acetate, 2:1);
1
oil; H NMR d 7.52–7.37 (m, 5H), 7.27–7.17 (m, 2H),
7.08–6.99 (m, 2H), 4.45 (q, 2H, J¼7 Hz), 2.40 (t, 2H,
J¼8 Hz), 1.51–1.37 (m, 5H), 1.23–1.13 (m, 4H), 0.79 (t,
3H, J¼7 Hz); 13C NMR d 161.47, 146.33, 137.49, 136.83,
132.16, 129.10, 128.75, 128.35, 127.95, 127.66, 122.02,
121.30, 113.55, 37.70, 32.08, 29.09, 28.76, 22.23, 13.98,
12.82. IR (KBr): nCvO 1637 cm21. Anal. Calcd for
C22H25NO: C, 82.72; H, 7.89; N, 4.38. Found: C, 82.80;
H, 7.81; N, 4.39.
4.4.1. Compound 3a. Rf 0.37 (hexane–ethyl acetate, 2:1);
1
mp 146 8C (lit.16a 146 8C); H NMR d 7.60–7.40 (m, 8H),
7.16 (t, 1H, J¼8 Hz), 6.68 (s, 1H), 3.78 (s, 3H); 13C NMR d