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H.R. Shaterian et al. / Tetrahedron 64 (2008) 1263e1269
4.4.1. N-[Phenyl-(2-hydroxy-napthalen-1-yl)-methyl]-
acetamide (Table 4, entry 1)
4.4.5. N-[(4-Bromophenyl)-(2-hydroxynaphthalen-1-yl)-
methyl]-acetamide (Table 4, entry 6)
Mp: 245e246 ꢀC (lit.10 mp: 241e243 ꢀC); 1H NMR
(500 MHz, DMSO-d6): d¼1.98 (s, 3H), 7.11 (m, 1H), 7.14
(m, 1H), 7.16 (m, 1H), 7.19 (m, 1H), 7.20 (m, 2H), 7.21 (m,
1H), 7.23 (m, 1H), 7.33 (t, J¼7.5 Hz, 1H), 7.73 (d, J¼9.1 Hz, 1H),
7.78 (d, J¼8.0 Hz, 1H), 7.83 (s, 1H), 8.45 (d, J¼8.5 Hz, 1H),
10.01 (s, 1H) ppm; 13C NMR (125 MHz, DMSO-d6): 23.2,
40.3, 119.2, 119.4, 122.9, 123.8, 126.6, 126.8, 128.5,
126.8, 128.9, 129.1, 129.8, 132.8, 143.1, 153.7, 169.0 ppm;
IR (KBr, cmꢁ1): 3399, 3246, 3062, 1640, 1582, 1514,
1372, 1337, 1060, 808, 742, 696, 623.
Mp: 227e229 ꢀC (lit.7 mp: 228e230 ꢀC); 1H NMR
(300 MHz, DMSO-d6): d¼2.02 (s, 3H), 7.41e7.05 (m, 8H),
7.83e7.67 (m, 2H), 7.92 (d, J¼11.3 Hz, 1H), 8.10 (d,
J¼8.2 Hz, 1H), 9.85 (s, 1H) ppm; IR (KBr, cmꢁ1): 3463,
3349, 2967, 1651, 1596, 1572, 1505, 1433, 1349, 1289, 1146,
1062, 826.
4.4.6. N-[(3-Nitro-phenyl)-(2-hydroxy-napthalen-1-yl)-
methyl]-acetamide (Table 4, entry 8)
Mp: 241e242 ꢀC (lit.8 mp: 182e184); 1H NMR (500 MHz,
DMSO-d6): d¼2.01 (s, 3H), 7.17 (t, J¼8.0 Hz, 1H), 7.19 (d,
J¼8.6 Hz, 1H), 7.24 (t, J¼7.5 Hz, 1H), 7.38 (t, J¼7.4 Hz,
1H), 7.51 (m, 2H), 7.78 (t, J¼8.6 Hz, 2H), 7.83 (br, 1H), 7.98
(m, 2H), 8.58 (d, J¼8.0 Hz, 1H), 10.16 (s, 1H) ppm; 13C
NMR (125 MHz, DMSO-d6): 23.1, 48.2, 118.3, 118.9, 120.9,
121.8, 123.2, 127.3, 123.2, 128.9, 129.2, 130.1, 130.5,
132.6, 133.4, 145.9, 148.2, 153.9, 170.3 ppm; IR (KBr, cmꢁ1):
3373, 3088, 2598, 1645, 1524, 1350, 1232, 1158, 1063, 808,
705.
4.4.2. N-[(4-Methyl-phenyl)-(2-hydroxy-napthalen-1-yl)-
methyl]-acetamide (Table 4, entry 2)
Mp: 222e223 ꢀC; 1H NMR (500 MHz, DMSO-d6): d¼1.96
(s, 3H), 2.21 (s, 3H), 7.03e7.08 (m, 5H), 7.19 (d, J¼8.8 Hz,
1H), 7.24 (t, J¼7.1 Hz, 1H), 7.34 (m, 1H), 7.74 (d, J¼8.8
Hz, 1H), 7.78 (d, J¼7.9 Hz, 1H), 7.82 (br, 1H), 8.36 (d, J¼8.1
Hz, 1H), 9.91 (s, 1H) ppm; 13C NMR (125 MHz, DMSO-d6):
20.4, 22.6, 47.6, 118.4, 118.9, 122.2, 123.1, 125.9, 126.1,
128.3, 128.4, 128.9, 132.2, 134.9, 139.4, 143.2, 152.9,
168.9 ppm; IR (KBr, cmꢁ1): 3396, 3055, 2923, 1625, 1515,
1437, 1276, 1181, 813, 744, 482; MS: m/z¼305 (Mþ, 21%),
246 (29.158%), 245 (50.55%), 231 (100%), 232 (31.20%),
202 (16.12%), 115 (10.04%). Anal. Calcd for C20H19NO2:
C, 78.66; H, 6.27; N, 4.59. Found: C, 78.72; H, 6.21; N, 4.63.
4.4.7. N-[(3-Fluoro-phenyl)-(2-hydroxy-napthalen-1-yl)-
methyl]-acetamide (Table 4, entry 9)
Mp: 248e249 ꢀC; 1H NMR (500 MHz, DMSO-d6): d¼1.98
(s, 3H), 6.92e6.98 (m, 3H), 7.12 (d, J¼8.3 Hz, 1H), 7.19e
7.27 (m, 3H), 7.37 (t, J¼7.3 Hz, 1H), 7.76 (d, J¼8.6 Hz, 1H),
7.80 (d, J¼8.0 Hz, 1H), 7.84 (br, 1H), 8.44 (d, J¼8.2 Hz, 1H),
10.01 (s, 1H) ppm; 13C NMR (125 MHz, DMSO-d6): 22.5,
2
2
4.4.3. N-[(4-Nitro-phenyl)-(2-hydroxy-napthalen-1-yl)-
methyl]-acetamide (Table 4, entry 3)
47.5, 112.5 (d, JCeF¼22.1 Hz), 112.7 (d, JCeF¼20.9 Hz),
118.3, 118.4, 122.1, 122.4, 122.9, 126.4, 128.3, 128.5, 129.4,
Mp: 248e250 ꢀC; 1H NMR (500 MHz, DMSO-d6): d¼2.02
(s, 3H), 7.19 (d, J¼8.0 Hz, 1H), 7.22 (d, J¼8.8 Hz, 1H), 7.28
(t, J¼7.5 Hz, 1H), 7.41 (t, J¼7.3 Hz, 1H), 7.52e7.58 (m, 2H),
7.81 (t, J¼9.4 Hz, 2H), 7.87 (d, J¼7.0 Hz, 1H), 8.03 (m, 2H),
8.60 (d, J¼8.0 Hz, 1H), 10.11 (s, 1H) ppm; 13C NMR
(125 MHz, DMSO-d6): 22.5, 47.6, 117.7, 118.4, 120.3, 121.1,
122.5, 126.6, 128.3, 129.4, 129.8, 132.1, 132.7, 145.3, 147.7,
153.2, 169.5 ppm; IR (KBr, cmꢁ1): 3391, 3267, 2593, 1648,
1603, 1522, 1438, 1063, 825, 739, 447; MS: m/z¼336 (Mþ,
26.66%), 319 (75.99%), 276 (52.02%), 260 (54.15%), 231
(63.80%), 202 (45.11%), 230 (100%), 115 (18.05%). Anal.
Calcd for C19H16N2O4: C, 67.85; H, 4.79; N, 8.33. Found: C,
67.91; H, 4.81; N, 8.24.
3
3
129.8 (d, JCeF¼8.1 Hz), 132.1, 145.9 (d, JCeF¼6.6 Hz),
153.1, 162.0 (d, 1JCeF¼241.2 Hz), 169.3 ppm; IR (KBr, cmꢁ1):
3410, 3160, 1640, 1589, 1545, 1484, 1439, 1335, 1280, 1064,
989, 814, 497; MS: m/z¼310 (4.79%), 309 (Mþ, 21.45%), 251
(9.00%), 250 (51.75%), 249 (100.00%), 231 (14.44%), 220
(16.11%), 122 (7.31%), 115 (9.01%). Anal. Calcd for
C19H16FNO2: C, 73.77; H, 5.21; N, 4.53. Found: C, 73.74; H,
5.25; N, 4.48.
4.4.8. N-[(4-Fluoro-phenyl)-(2-hydroxy-napthalen-1-yl)-
methyl]-acetamide (Table 4, entry 10)
Mp: 230e232 ꢀC (lit.8 mp: 209e210); 1H NMR (500 MHz,
DMSO-d6): d¼1.95 (s, 3H), 7.02 (t, J¼9.1 Hz, 2H), 7.07 (d,
J¼8.0 Hz, 1H), 7.13 (m, 2H), 7.18 (t, J¼8.0 Hz, 1H), 7.23 (t, J¼
7.5 Hz, 1H), 7.31 (t, J¼8.0 Hz, 1H), 7.73 (m, 3H), 8.46 (d,
J¼8.6 Hz, 1H), 10.03 (s, 1H) ppm; 13C NMR (125 MHz,
DMSO-d6): 23.2, 47.9, 115.1, 115.3, 119.0, 119.1, 122.9,
126.9, 128.4, 128.5, 128.9, 129.1, 129.9, 132.7, 139.2, 153.6,
160.3, 162.2, 169.7 ppm; IR (KBr, cmꢁ1): 3392, 2974, 1627,
1576, 1508, 1438, 1334, 1225, 1062, 823, 748, 601, 489.
4.4.4. N-[(4-Chloro-phenyl)-(2-hydroxy-napthalen-1-yl)-
methyl]-acetamide (Table 4, entry 5)
Mp: 223e225 ꢀC (lit.8 mp: 224e227 ꢀC); 1H NMR
(500 MHz, DMSO-d6): d¼1.96 (s, 3H), 7.05 (d, J¼8.1 Hz,
1H), 7.11 (d, J¼8.6 Hz, 2H), 7.18 (d, J¼8.6 Hz, 1H), 7.19 (m,
3H), 7.31 (t, J¼7.5 Hz, 1H), 7.73 (m, 3H), 8.42 (d, J¼8.6 Hz,
1H), 10.09 (s, 1H) ppm; 13C NMR (125 MHz, DMSO-d6):
20.6, 23.1, 48.1, 118.9, 119.0, 123.0, 126.9, 128.9, 128.4,
129.1, 129.1, 130.0, 131.2, 132.7, 142.3, 153.7, 169.9 ppm; IR
(KBr, cmꢁ1): 3392, 2962, 2700, 2613, 1637, 1577, 2523,
1490, 1436, 1374, 1331, 1278, 1243, 1171, 1091, 819, 747,
588, 499.
4.4.9. N-[(2,4-Dichloro-phenyl)-(2-hydroxy-napthalen-1-yl)-
methyl]-acetamide (Table 4, entry 11)
Mp: 201e203 ꢀC (lit.8 mp: 198e199); 1H NMR (500 MHz,
DMSO-d6): d¼1.88 (s, 3H), 6.96 (d, J¼7.5 Hz, 1H), 7.11 (d,
J¼9.2 Hz, 1H), 7.27 (t, J¼7.5 Hz, 1H), 7.35 (m, 3H), 7.54