792
H. R. Shaterian et al. / Bioorg. Med. Chem. Lett. 18 (2008) 788–792
2, Method C). The reaction was followed by TLC. After
129.7, 132.1, 132.7, 139.7, 153.5, 168.4 ppm; IR (KBr,
cmÀ1): 3427, 3061, 1640, 1577, 1514, 1471, 1438, 1371, 1268,
1163, 1063, 808, 752, 711, 668. MS: m/z = 327 (3.93%), 326
(4.13%), 325 (M+, 14.37%), 290 (9.69%), 232 (23.55%), 231
(100.00%), 115 (7.48%).
completion of reaction, mass was cooled to 25 °C, then the
solid residue was solved in boiling EtOH and the mixture
stirred for 5 min. The catalyst was recovered. Then
solution was cooled to room temperature, the solid so
obtained was filtered and recrystallized from aqueous
EtOH (15%). Some physical data of these compounds are
represented below:
N-[Phenyl-(2-hydroxy-naphthalen-1-yl)-methyl]-acetamide
(Table 2, entry 1): [mp: 245–246 °C]; 1H NMR (500 MHz,
DMSO-d6): d = 1.98 (s, 3H), 7.19–1.10 (m, 4H), 7.26–7.20
(m, 4H), 7.33 (t, J = 7.5 Hz, 1H), 7.74 (d, J = 9.2 Hz, 1H,),
7.80 (d, J = 8.0 Hz, 1H), 7.84 (s, 1H), 8.45 (d, J = 8.5 Hz,
1H), 10.02 (s, 1H) ppm; 13C NMR (125 MHz, DMSO-d6):
23.2, 40.4, 119.2, 119.4, 122.9, 123.8, 126.6, 126.9, 128.5,
128.7, 128.9, 129.1, 129.8, 132.9, 143.1, 153.7, 169.1 ppm;
IR (KBr, cmÀ1): 3399, 3246, 3062, 1640, 1582, 1514, 1372,
1337, 1060, 808, 742, 696, 623.
N-[(4-Methyl phenyl)-(2-hydroxy-naphthalen-1-yl)-methyl]-
acetamide (Table 2, entry 14): [mp: 222–223 °C]; 1H NMR
(500 MHz, DMSO-d6): d = 1.96 (s, 3H), 2.21 (s, 3H), 7.08–
7.03 (m, 5H), 7.19 (d, J = 8.8 Hz, 1H), 7.24 (t,J = 7.1 Hz,
1H), 7.34 (m, 1H), 7.74 (d, J = 8.8 Hz, 1H), 7.78 (d,
J = 7.9 Hz, 1H), 7.82 (br d, 1H), 8.36 (d, J = 8.1 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, 143.3, 152.9, 168.9 ppm;
IR (KBr, cmÀ1): 3419, 3316, 3070, 1621, 1595, 1561, 1514,
1466, 1392, 1283, 1202, 1141, 1051, 939, 884, 784, 745, 712;
MS: m/z = 305 (M+, 21.00%), 246 (29.16%), 245 (50.55%),
231 (100.00%), 232 (31.20%), 202 (16.12%), 115 (10.04%).
N-[(4-Nitro-phenyl)-(2-hydroxy-naphthalen-1-yl)-methyl]-
acetamide (Table 2, entry 15): (mp: 248–250 °C); 1H NMR
(500 MHz, DMSO-d6): d = 2.02 (s, 3H), 7.19 (d, J = 8.0,
1H), 7.22 (d, J = 8.8, 1H), 7.28 (t, J = 7.47 Hz, 1H), 7.41 (t,
J = 7.34, 1H), 7.52–7.58 (m, 2H), 7.81 (t, J = 9.38 Hz, 2H),
7.89 (br d, 1H), 8.05–8.03 (m, 2H), 8.60 (d, J = 8.0 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, 126.7, 128.6, 129.4,
129.8, 132.1, 132.7, 145.3, 147.7, 153.2, 169.5 ppm; IR (KBr,
cmÀ1): 3391, 3267, 2593, 1648, 1603, 1522, 1438, 1063, 825,
739, 447; MS: m/z = 336 (M+, 26.66%), 319 (75.99%), 276
(52.02%), 260 (54.15%), 231 (63.80%), 202 (45.11%), 230
(100.00%), 115 (18.05%).
N-[(3-Nitro phenyl)-(2-hydroxy-naphthalen-1-yl)-methyl]-
1
acetamide (Table 2, entry 6): [mp: 241–242 °C]; H NMR
(500 MHz, DMSO-d6): d = 2.01 (s, 3H), 7.17 (t, J = 8.0 Hz,
1H), 7.19 (d, J = 8.6 Hz, 1H), 7.24 (t, J = 7.4 Hz, 1H), 7.38
(t, J = 7.4 Hz, 1H), 7.51 (m, 2H), 7.78 (t, J = 8.6 Hz, 2H),
7.83 (br, 1H), 7.97–7.99 (m, 2H), 8.58 (d, J = 8.0 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, 123.1, 127.3, 123.2, 128.9,
129.2, 130.1, 130.5, 132.7, 133.4, 145.9, 148.2, 153.9,
170.3 ppm; IR (KBr, cmÀ1): 3373, 3088, 2598, 1645, 1524,
1350, 1232, 1158, 1063, 808, 705.
N-[(4-Fluoro phenyl)-(2-hydroxy naphthalen-1-yl)-methyl]-
1
acetamide (Table 2, entry 7): [mp: 230–232 °C]; H NMR
(500 MHz, DMSO-d6): d = 1.96 (s, 3H), 7.04 (d, J = 8.8 Hz,
1H), 7.08 (d, J = 9.7 Hz, 2H), 7.15 (t, J =
5.6 Hz, 2H), 7.20 (d, J = 8.8 Hz, 1H), 7.25 (t,
J = 7.3 Hz,1H), 7.36 (t, J = 7.3 Hz, 1H), 7.75 (d, J =
8.8 Hz, 1H), 7.79 (d, J = 8.1 Hz, 1H), 7.82 (br d, 1H), 8.41
(d, J = 8.3 Hz, 1H), 9.97 (s, 1H) ppm; 13C NMR (125 MHz,
N-[(3-Fluoro phenyl)-(2-hydroxy naphthalen-1-yl)-methyl]-
acetamide (Table 2, entry 16): [mp: 248–249 °C]; 1H NMR
(500 MHz, DMSO-d6): d = 1.98 (s, 3H), 6.98–6.92 (m, 3H),
7.12 (d, J = 8.3 Hz, 1H), 7.27–7.19 (m, 3H), 7.37 (t,
J = 7.3 Hz, 1H), 7.76 (d, J = 8.6 Hz, 1H), 7.80 (d,
J = 8.0 Hz, 1H), 7.84 (br d, 1H), 8.44 (d, J = 8.2 Hz, 1H),
10.01 (s, 1H) ppm; 13C NMR (125 MHz, DMSO-d6): 22.5,
47.5, 112.5 (d, 2JC–F = 22.1 Hz), 112.7 (d, 2JC–F = 20.9 Hz),
118.3, 118.4, 122.1 (d, 4JC–F = 2.5 Hz), 122.4, 122.9, 126.4,
DMSO-d6):
22.5,
47.3,
114.6
(d,
21.1 Hz), 118.4, 118.5, 122.3, 122.9, 126.2, 127.8 (d,
2JC–F
=
3JC–F = 8 Hz), 128.3, 128.4, 129.2, 132.1, 138.6, 153.0,
1
3
160.6 (d, JC–F = 240.2 Hz), 169.1 ppm; IR (KBr, cmÀ1):
128.3, 128.5, 129.4, 129.8 (d, JC–F = 8.1 Hz), 132.1, 145.9
3
1
3392, 2974, 1627, 1576, 1508, 1438, 1334, 1225, 1062, 823,
748, 601, 489.
(d, JC–F = 6.6 Hz), 153.1, 162.0 (d, JC–F = 241.2 Hz),
169.3 ppm; IR (KBr, cmÀ1): 3410, 3160, 1640, 1589, 1545,
1484, 1439, 1335, 1280, 1064, 989, 814, 760, 743. MS: m/z =
310 (4.79%), 309 (M+, 21.45%), 251 (9.00%), 250 (51.75%),
249(100.00%), 231(14.44%), 220(16.11%), 122(7.31%), 115
(9.01%). N-[(2,5-Dimethoxy phenyl)-(2-hydroxy-naphtha-
len-1-yl)-methyl]-acetamide (Table 2, entry 17): [mp: 251–
253 °C]; 1H NMR (500 MHz, DMSO-d6): d = 1.88 (s, 3H),
3.48 (s, 3H), 3.64 (s, 3H), 6.77–6.72 (m, 2H), 7.23–7.10 (m,
4H), 7.39 (s, 1H), 7.73–7.66 (m, 2H), 8.27–8.15 (m, 2H), 9.75
(s, 1H) ppm; 13C NMR (125 MHz, DMSO-d6): 22.5, 44.4,
55.2, 55.9, 111.1, 111.9, 115.7, 118.5, 118.9, 122.0, 123.2,
125.7, 128.1, 128.6, 131.7, 132.4, 150.7, 152.7, 153.1,
168.1 ppm; IR (KBr, cmÀ1): 3365, 3174, 3002, 2939, 1614,
1577, 1497, 1436, 1370, 1317, 1277, 1218, 1084, 1052, 819,
797, 727; MS: m/z = 351 (M+, 17.83%), 308 (5.82%), 276
(5.87%), 262 (36.04%), 261 (100.00%), 218 (16.71%), 144
(6.60%), 115 (7.99%).
N-[(2,4-Dichloro
phenyl)-(2-hydroxy-naphthalen-1-yl)-
methyl]-acetamide (Table 2, entry 8): [mp: 201–203 °C];
1H NMR (500 MHz, DMSO-d6): d = 1.88 (s, 3H), 6.96 (d,
J = 7.4 Hz, 1H), 7.11 (d, J = 9.2 Hz, 1H), 7.27 (t, J = 7.4 Hz,
1H), 7.34–7.32 (m, 3H), 7.54 (d, J = 8.6 Hz, 1H), 7.70 (d,
J = 8.6 Hz, 1H), 7.76 (d, J = 8 Hz, 1H), 7.91 (d, J = 8.6 Hz,
1H), 8.59 (d, J = 8.0 Hz, 1H), 9.81 (br d, 1H) ppm; 13C
NMR (125 MHz, DMSO-d6): 22.9, 47.8, 117.8, 119.1,
122.9, 123.1, 126.9, 127.1, 128.7, 128.9, 129.2, 130.2,
131.7, 132.1, 133.2, 133.3, 139.8, 154.2, 169.3 ppm; IR
(KBr, cmÀ1): 3404, 3116, 1649, 1579, 1516, 1438, 1279, 1162,
812, 583, 458.
N-[(2-Chloro phenyl)-(2-hydroxy naphthalen-1-yl)-methyl]-
1
acetamide (Table 2, entry 9): [mp: 213–215 °C]; H NMR
(500 MHz, DMSO-d6): d = 1.91 (s, 3H), 7.56–7.08 (m, 8H),
7.73 (d, J = 7.6 Hz, 1H), 7.78 (d, J = 6.1 Hz, 1H), 8.00 (d,
J = 7.0 Hz, 1H), 8.50 (s, 1H), 9.75 (s, 1H) ppm; 13C NMR
(125 MHz, DMSO-d6): 22.3, 47.5, 117.0, 118.5, 122.1,
122.7, 126.1, 126.2, 127.9, 128.2, 128.4, 129.1, 129.2,
17. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic
Chemistry; University Science Books: Sausalito, Califor-
nia, 2006.