5598
A. T. Khan et al. / Tetrahedron 63 (2007) 5593–5601
(EtOAc–hexane), mp 146 ꢁC (lit.8 mp 146–148 ꢁC) [Found:
C, 67.53; H, 5.28; N, 4.72. C17H16ClNO2 requires C, 67.66;
H, 5.34; N, 4.64%]; nmax (KBr): 3291, 2329, 1687, 1647,
1547, 1445, 1349, 1229, 1009, 754 cmꢂ1; dH (400 MHz,
CDCl3) 2.01 (3H, s, COMe), 3.41 (1H, dd, J 6.0, 16.8 Hz,
CH2), 3.73 (1H, dd, J 5.2, 17.2 Hz, CH2), 5.50–5.55 (1H,
m, CH), 6.74 (1H, d, J 7.2 Hz, NH), 7.25 (4H, d, J 4.4 Hz,
Ph), 7.44 (2H, t, J 8.0 Hz, Ph), 7.56 (1H, t, J 7.6 Hz, Ph),
7.87 (2H, d, J 8.4 Hz, Ph); dC (100 MHz, CDCl3) 23.0,
43.2, 49.4, 128.1, 128.3, 128.9, 133.6, 133.9, 140.0, 142.0,
148.0, 165.0, 198.7.
J 5.2, 16.8 Hz, CH2), 3.76 (3H, s, OMe), 3.78 (6H, s,
2ꢀOMe), 5.44 (1H, q, J 7.6 Hz, CH), 6.52 (2H, s, Ph),
6.67 (1H, d, J 7.6 Hz, NH), 7.43 (2H, t, J 7.6 Hz, Ph), 7.55
(1H, t, J 7.2 Hz, Ph), 7.88 (2H, d, J 8.0 Hz, Ph); dC
(100 MHz, CDCl3) 23.7, 43.4, 50.7, 56.3, 60.9, 103.9,
128.3, 128.9, 133.8, 136.8, 136.9, 153.5, 156.2, 169.5, 199.4.
4.2.7. N-[1-(2-Nitrophenyl)-3-oxo-3-phenyl-propyl] acet-
amide (1g).6 Yield 90% (560.0 mg), white solid, mp 190–
191 ꢁC (lit.6 mp 186–188 ꢁC) [Found: C, 65.49; H, 5.23;
N, 8.88. C17H16N2O4 requires C, 65.38; H, 5.16; N,
8.97%]; nmax (KBr): 3326, 2379, 1686, 1651, 1544, 1517,
1357, 1337, 1059, 682 cmꢂ1; dH (400 MHz, CDCl3) 2.00
(3H, s, COMe), 3.63 (1H, dd, J 5.6, 16.8 Hz, CH2), 3.71
(1H, dd, J 6.4, 17.2 Hz, CH2), 5.93–5.97 (1H, m, CH),
7.07 (1H, d, J 5.6 Hz, NH), 7.39 (1H, t, J 8.0 Hz, Ph), 7.46
(2H, t, J 8.0 Hz, Ph), 7.57 (2H, t, J 7.6 Hz, Ph), 7.71 (1H,
d, J 8.0 Hz, Ph), 7.92 (2H, d, J 7.2 Hz), 7.94 (1H, d, J 6.8,
Ph); dC (100 MHz, CDCl3) 23.5, 42.4, 47.7, 125.3, 128.5,
128.6, 129.0, 130.1, 133.7, 134.1, 136.5, 137.1, 148.7,
169.5, 198.5.
4.2.3. N-[1-(4-Bromophenyl)-3-oxo-3-phenyl-propyl]
acetamide (1c). Yield 98% (678.0 mg), white crystal
(EtOAc–hexane), mp 148–150 ꢁC [Found: C, 58.85; H,
4.70; N, 4.12. C17H16BrNO2 requires C, 58.98; H, 4.66; N,
4.05%]; nmax (KBr): 3285, 2923, 1684, 1651, 1550, 1374,
1292, 1006, 757 cmꢂ1; dH (400 MHz, CDCl3) 2.02 (3H, s,
COMe), 3.40 (1H, dd, J 6.0, 17.2 Hz, CH2), 3.72 (1H, dd,
J 5.2, 16.8 Hz, CH2), 5.49–5.51 (1H, m, CH), 6.73 (1H, d,
J 6.8, NH), 7.19 (2H, d, J 8.4 Hz, Ph), 7.40 (2H, d, J
8.4 Hz, Ph), 7.44 (2H, d, J 8.0 Hz, Ph), 7.55 (1H, t, J
7.2 Hz, Ph), 7.87 (2H, d, J 7.2 Hz, Ph); dC (100 MHz,
CDCl3) 23.7, 42.9, 49.4, 128.3, 128.4, 129.0, 131.9, 134.0,
136.2, 140.2, 166.5, 196.5.
4.2.8. N-[1-(3-Nitrophenyl)-3-oxo-3-phenyl-propyl] acet-
amide (1h).6 Yield 96% (593.0 mg), white solid, mp 139–
140 ꢁC (lit.10 mp 139–140 ꢁC) [Found: C, 65.29; H, 5.22;
N, 8.88. C17H16N2O4 requires C, 65.38; H, 5.16; N,
8.97%]; nmax (KBr): 3306, 1693, 1644, 1545, 1522, 1347,
983, 684 cmꢂ1; dH (400 MHz, CDCl3) 2.08 (3H, s,
COMe), 3.51 (1H, dd, J 5.6, 17.6 Hz, CH2), 3.79 (1H, dd,
J 5.2, 17.6 Hz, CH2), 5.62–5.67 (1H, m, CH), 6.91 (1H, d,
J 7.6 Hz, NH), 7.42–7.49 (3H, m, Ph), 7.57 (1H, t, J
7.6 Hz, Ph), 7.68 (1H, d, J 7.6 Hz, Ph), 7.87 (2H, d, J
7.6 Hz, Ph), 8.06 (1H, d, J 6.8 Hz, Ph), 8.19 (1H, s, Ph);
dC (100 MHz, CDCl3) 23.6, 42.9, 49.3, 121.5, 122.6,
128.3, 129.1, 129.8, 130.8, 133.1, 134.2, 136.4, 143.7,
169.9, 198.3.
4.2.4. N-[1-(4-Methoxyphenyl)-3-oxo-3-phenyl-propyl]
acetamide (1d).10 Yield 94% (560.0 mg), white crystal
(EtOAc–hexane), mp 110–111 ꢁC (lit.10 mp 110–112 ꢁC)
[Found: C, 72.59; H, 6.49; N, 4.79. C18H19NO3 requires C,
72.71; H, 6.44; N, 4.71%]; nmax (KBr): 3301, 2928, 1688,
1648, 1545, 1372, 1238, 1033, 754 cmꢂ1; dH (400 MHz,
CDCl3) 2.0 (3H, s, COMe), 3.39 (1H, dd, J 6.4, 16.8 Hz,
CH2), 3.72 (1H, dd, J 5.2, 17.2 Hz, CH2), 3.74 (3H, s,
OMe), 5.46–5.51 (1H, m, CH), 6.57 (1H, d, J 8.0 Hz, NH),
6.81 (2H, d, J 8.4 Hz, Ph), 7.23 (2H, d, J 8.0 Hz, Ph), 7.42
(2H, t, J 7.6 Hz, Ph), 7.54 (1H, t, J 7.2 Hz, Ph), 7.89 (2H,
d, J 7.2 Hz, Ph); dC (100 MHz, CDCl3) 23.6, 43.5, 49.7,
55.4, 114.2, 127.9, 128.3, 128.9, 133.1, 133.7, 136.7,
158.9, 169.7, 198.8.
4.2.9. N-[1-(4-Nitrophenyl)-3-oxo-3-phenyl-propyl] acet-
amide (1i).6 Yield 95% (593.0 mg), yellow crystalline solid,
mp 153 ꢁC (lit.10 mp 154 ꢁC) [Found: C, 65.29; H, 5.23; N,
8.99. C17H16N2O4 requires C, 65.38; H, 5.16; N, 8.97%];
nmax (KBr): 3306, 1696, 1646, 1595, 1537, 1350, 988,
755 cmꢂ1; dH (400 MHz, CDCl3) 2.10 (3H, s, COMe), 3.51
(1H, dd, J 5.6, 17.6 Hz, CH2), 3.81 (1H, dd, J 5.2, 17.6 Hz,
CH2), 5.65–5.67 (1H, m, CH), 6.96 (1H, d, J 8.0 Hz, NH),
7.47 (2H, t, J 8.0 Hz, Ph), 7.51 (2H, d, J 8.8 Hz, 2H, Ph),
7.60 (1H, t, J 7.2 Hz, Ph), 7.89 (2H, d, J 7.2 Hz, Ph), 8.17
(2H, d, J 8.8 Hz, Ph); dC (100 MHz, CDCl3) 23.5, 42.6,
49.2, 123.7, 127.2, 127.9, 128.7, 131.0, 133.9, 136.0,
138.4, 169.5, 197.8.
4.2.5. N-[1-(3,4-Dimethoxyphenyl)-3-oxo-3-phenyl-pro-
pyl] acetamide (1e). Yield 98% (640.0 mg), brownish solid,
mp 118–119 ꢁC [Found: C, 69.58; H, 6.40; N, 4.37.
C19H21NO4 requires C, 69.71; H, 6.47; N, 4.28%]; nmax
(KBr): 3247, 3076, 2917, 2846, 1681, 1637, 1519, 1462,
1253, 1026, 751 cmꢂ1; dH (400 MHz, CDCl3) 2.01 (3H, s,
COMe), 3.39 (1H, dd, J 6.4, 16.8 Hz, CH2), 3.72 (1H, dd,
J 5.2, 16.4 Hz, CH2), 3.81 (3H, s, OMe), 3.82 (3H, s,
OMe), 5.45–5.50 (1H, m, CH), 6.58 (1H, d, J 8.0 Hz, NH),
6.76 (1H, d, J 8.0 Hz, Ph), 6.83 (2H, s+d, J 8.0 Hz, Ph),
7.43 (2H, t, J 7.6 Hz, Ph), 7.55 (1H, t, J 7.6 Hz, Ph), 7.89
(2H, d, J 7.2 Hz, Ph); dC (100 MHz, CDCl3) 23.7, 43.4,
50.1, 56.1, 110.5, 111.3, 118.3, 128.3, 128.9, 133.6, 133.7,
149.2, 169.6, 199.0.
4.2.10. N-[1-(4-Styryl)-3-oxo-3-phenyl-propyl] acet-
amide (1j). Yield 85% (497.0 mg), light yellow solid, mp
120–121 ꢁC [Found: C, 77.68; H, 6.45; N, 4.83.
C19H19NO2 requires C, 77.79; H, 6.53; N, 4.77%]; nmax
(KBr): 3291, 3065, 2928, 1687, 1648, 1635, 1547, 1445,
1366, 1083, 751 cmꢂ1; dH (400 MHz, CDCl3) 2.04 (3H, s,
COMe), 3.35 (1H, dd, J 5.6, 17.6 Hz, CH2), 3.53 (1H, dd,
J 4.4, 17.6 Hz, CH2), 5.09–5.13 (1H, m, CH), 6.33 (1H,
dd, J 6.8, 16.0 Hz, CH]), 6.54 (1H, d, J 15.6 Hz, CH]),
7.20 (1H, d, J 6.8 Hz, NH), 7.25 (2H, t, J 6.8 Hz, Ph), 7.29
(3H, d, J 7.2 Hz, Ph), 7.46 (2H, t, J 7.6 Hz, Ph), 7.57 (1H,
t, J 7.6 Hz, Ph), 7.93 (2H, d, J 7.2 Hz, Ph); dC (100 MHz,
4.2.6. N-[1-(3,4,5-Trimethoxyphenyl)-3-oxo-3-phenyl-
propyl] acetamide (1f). Yield 96% (685.0 mg), white solid,
mp 168–169 ꢁC [Found: C, 67.34; H, 6.42; N, 3.99.
C20H23NO5 requires C, 67.21; H, 6.49; N, 3.92%]; nmax
(KBr): 3276, 2928, 1688, 1648, 1592, 1458, 1339, 1246,
1001, 754 cmꢂ1; dH (400 MHz, CDCl3) 2.01 (3H, s,
COMe), 3.37 (1H, dd, J 6.0, 16.8 Hz, CH2), 3.69 (1H, dd,