5806
H. R. Shaterian et al. / Tetrahedron Letters 49 (2008) 5804–5806
21. Methyl (2-hydroxynaphthalen-1-yl)(phenyl)methyl carbamate (Table 2, entry 1):
1H NMR (300 MHz, DMSO-d6): d 3.57 (s, 3H), 6.87 (d, J = 8.4 Hz, 1H), 7.18–7.29
(m, 7H), 7.38 (d, J = 7.4 Hz, 1H), 7.65–7.84 (m, 3H), 7.92 (d, J = 7.7 Hz, 1H), 10.12
(s, 1H, OH) ppm; 13C NMR (75 MHz, DMSO-d6): d 50.8, 52.1, 118.9, 119.3, 123.0,
123.5, 126.5, 126.8, 127.0, 128.6, 128.8, 129.0, 129.8, 132.5, 142.8, 153.4,
157.0 ppm; IR (KBr, cmÀ1): 3423, 3202, 1677, 1630, 1585, 1518, 1438, 1335,
1272, 1066, 1042, 937, 811, 743, 697; MS (EI, 70 eV): m/z (%) = 307 (M+, 13),
295 (9), 279 (15), 232 (79), 231 (100), 202 (16), 167 (31), 149 (76), 115 (10),
104 (10), 71 (14), 57 (18), 43 (10); Anal. Calcd for: C19H17NO3: C, 74.25; H, 5.58;
N, 4.56%. Found: C, 74.23; H, 5.57; N, 4.52%.
22. Methyl (2-hydroxynaphthalen-1-yl)(4-nitrophenyl)methyl carbamate (Table 2,
entry 2): 1H NMR (300 MHz, DMSO-d6): d 3.60 (s, 3H), 6.95 (d, J = 8.3 Hz, 1H),
7.22 (d, J = 8.8 Hz, 1H), 7.28 (t, J = 7.2 Hz, 1H), 7.39 (d, J = 7.7 Hz, 1H), 7.47 (d,
J = 8.5 Hz, 2H), 7.78–7.87 (m, 4H), 8.15 (d, J = 8.6 Hz, 2H), 10.22 (s, 1H,
OH) ppm; 13C NMR (75 MHz, DMSO-d6): d 50.6, 52.3, 118.4, 118.8, 123.1, 123.3,
123.8, 127.3, 127.6, 128.8, 129.1, 130.4, 132.4, 146.5, 151.2, 153.6, 157.2 ppm;
IR (KBr, cmÀ1): 3422, 3265, 1683, 1628, 1604, 1518, 1438, 1346, 1272, 1247,
1068, 1046, 852, 823, 782, 741, 704; MS (EI, 70 eV): m/z (%) = 352 (M+, 17), 276
(21), 260 (85), 231 (36), 230 (100), 202 (25), 115 (10); Anal. Calcd for:
1H), 7.17 (d, J = 8.9 Hz, 2H), 7.27 (t, J = 7.0 Hz, 1H),7.43–7.54 (m, 2H), 7.72 (d,
J = 8.8 Hz, 1H), 7.77 (d, J = 8.1 Hz, 1H), 8.24 (d, J = 8.6 Hz, 1H, NH), 10.07 (s, 1H,
OH) ppm; 13C NMR (75 MHz, DMSO-d6): d 47.1, 51.9, 55.7, 56.4, 111.9, 112.2,
116.0, 119.1, 119.2, 122.8, 123.7, 126.5, 128.6, 128.7, 129.4, 131.8, 132.8, 151.0,
153.2, 153.5, 156.4 ppm; IR (KBr, cmÀ1): 3403, 3245, 3019, 2952, 2908, 1679,
1626, 1578, 1526, 1498, 1405, 1307, 1296, 1245, 1194, 1090, 856, 818, 750,
719; MS (EI, 70 eV): m/z (%) = 367 (M+, 7), 335 (16), 262 (42), 261 (100), 218
(18); Anal. Calcd for C21H21NO5: C, 68.65; H, 5.76; N, 3.81%. Found: C, 68.58; H,
5.75; N, 3.83%.
28. Benzyl (2-hydroxynaphthalen-1-yl)(phenyl)methyl carbamate (Table 2, entry 11):
1H NMR (300 MHz, DMSO-d6): d 5.04 (d, J = 12.5 Hz, 1H), 5.11 (d, J = 12.5 Hz,
1H), 6.92 (d, J = 8.6 Hz, 1H), 7.16–7.36 (m, 13H), 7.76–7.82 (m, 3H), 7.92 (d,
J = 7.5 Hz, 1H, NH), 10.13 (s, 1H, OH) ppm; 13C NMR (75 MHz, DMSO-d6): d
50.8, 66.1, 118.9, 119.3, 122.9, 126.5, 126.8, 126.9, 128.2, 128.6, 128.8, 128.9,
129.0, 129.8, 132.5, 137.5, 142.8, 153.4, 156.5 ppm; IR (KBr, cmÀ1): 3423, 3200,
3064, 3034, 1675, 1629, 1581, 1514, 1438, 1328, 1271, 1221, 1132, 1040, 943,
808, 753, 697; MS (EI, 70 eV): m/z (%) = 383 (M+, 7), 281 (9), 232 (74), 231
(100), 202 (13), 115 (9), 91 (47); Anal. Calcd for C25H21NO3: C, 78.31; H, 5.52; N,
3.65%. Found: C, 78.25; H, 5.69; N, 3.64%.
C
19H16N2O5: C, 64.77; H, 4.58; N, 7.95%. Found: C, 64.75; H, 4.58; N, 7.91%.
29. Benzyl (2-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl carbamate (Table 2,
entry 12): 1H NMR (300 MHz, DMSO-d6): d 5.02 (d, J = 12.7 Hz, 1H), 5.10 (d,
J = 12.9 Hz, 1H), 6.95 (d, J = 8.0 Hz, 1H), 7.17 (d, J = 8.7 Hz, 1H), 7.24–7.53 (m,
11H), 7.76 (d, J = 9.1 Hz, 1H), 7.81 (d, J = 8.1 Hz, 1H, NH), 8.04 (t, J = 8.1 Hz, 2H),
9.96 (s, 1H, OH) ppm; 13C NMR (75 MHz, DMSO-d6): d 50.2, 65.8, 117.4, 119.0,
122.8, 123.4, 126.8, 127.0, 127.9, 128.1, 128.7, 128.9, 129.1, 129.8, 130.0, 130.4,
133.0, 133.1, 137.6, 139.8, 154.0, 156.1 ppm; IR (KBr, cmÀ1): 3421, 3170, 3062,
3030, 1700, 1627, 1579, 1516, 1476, 1437, 1375, 1335, 1274, 1247, 1050, 819,
753, 733; MS (EI, 70 eV): m/z (%) = 417 (M+, 7), 282 (12), 232 (32), 231 (100),
202 (12), 115 (8), 91 (61); Anal. Calcd for C25H20ClNO3: C, 71.85; H, 4.82; N,
3.35%. Found: C, 71.65; H, 4.77; N, 3.30%.
30. Benzyl (3-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl carbamate (Table 2,
entry 13): 1H NMR (300 MHz, DMSO-d6): d 5.00 (d, J = 12.8 Hz, 1H), 5.08 (d,
J = 12.8 Hz, 1H), 6.93 (d, J = 7.6 Hz, 1H), 7.15 (d, J = 8.6 Hz, 1H), 7.26–7.37 (m,
10H), 7.52 (s, 1H), 7.74–7.81 (m, 2 H), 8.02–8.05 (m, 2H) 9.93 (s, 1H, OH) ppm;
13C NMR (75 MHz, DMSO-d6): d 50.2, 65.8, 117.4, 119.0, 122.8, 123.4, 126.8,
127.0, 127.9, 128.1, 128.7, 128.9, 129.1, 129.8, 130.0, 130.4, 133.1, 137.6, 139.8,
154.0, 156.1 ppm; IR (KBr, cmÀ1): 3421, 3170, 1701, 1628, 1579, 1517, 1438,
1377, 1335, 1275, 1248, 1050, 940, 819, 753, 734, 694, 530; MS (EI, 70 eV): m/z
(%) = 417 (M+, 4), 415 (6), 295 (8), 282 (6), 232 (22), 231 (100), 202 (13), 115
(8), 91 (40), 77 (7); Anal. Calcd for C25H20ClNO3: C, 71.85; H, 4.82; N, 3.35%.
Found: C, 71.82; H, 4.85; N, 3.33%.
31. Benzyl (2-hydroxynaphthalen-1-yl)(3-methoxyphenyl)methyl carbamate (Table 2,
entry 14): 1H NMR (300 MHz, DMSO-d6): d 3.66 (s, 3H), 5.03 (d, J = 12.6 Hz, 1H),
5.11 (d, J = 12.6 Hz, 1H), 6.74–6.88 (m, 4H), 7.13–7.35 (m, 9H), 7.74–7.81 (m,
3H), 7.90 (d, J = 7.9 Hz, 1H, NH), 10.06 (s, 1H, OH) ppm; 13C NMR (75 MHz,
DMSO-d6): d 50.7, 55.3, 66.1, 111.6, 112.8, 118.9, 119.2, 122.9, 123.6, 126.9,
128.2, 128.8, 129.0, 129.7, 129.8, 132.5, 137.5, 144.5, 153.4, 156.5, 159.6 ppm;
IR (KBr, cmÀ1): 3406, 3274, 3063, 3008, 2945, 1699, 1625, 1609, 1582, 1508,
1454, 1326, 1294, 1244, 1129, 1040, 961, 816, 771, 744; MS (EI, 70 eV): m/z
(%) = 413 (M+, 10), 278 (14), 262 (62), 261 (61), 232 (21), 231 (100), 91 (62);
Anal. Calcd for C26H23NO4: C, 75.53; H, 5.61; N, 3.39%. Found: C, 75.45; H, 5.58;
N, 3.40%.
32. Benzyl (4-fluorophenyl)(2-hydroxynaphthalen-1-yl)methyl carbamate (Table 2,
entry 15): 1H NMR (300 MHz, DMSO-d6): d 5.04 (d, J = 12.6 Hz, 1H), 5.10 (d,
J = 12.6 Hz, 1H), 6.89 (d, J = 8.3 Hz, 1H), 7.05–7.12 (m, 2H), 7.21–7.35 (m, 10H),
7.76–7.86 (m, 3H), 7.92 (d, J = 8.0 Hz, 1H, NH), 10.2 (s, 1H, OH) ppm; 13C NMR
(75 MHz, DMSO-d6): d 50.38, 66.2, 115.1, 115.4, 118.9, 119.0, 123.0, 123.5,
127.0, 128.3, 128.4, 128.5, 128.5, 128.9, 129.0, 129.9, 132.4, 137.4, 138.8, 153.4,
156.5, 159.7 ppm; IR (KBr, cmÀ1): 3424, 3247, 3072, 2968, 1676, 1268, 1562,
1507, 1455, 1438, 1327, 1273, 1219, 1160, 1066, 944, 854, 815, 755, 703; MS
(EI, 70 eV): m/z (%) = 401 (M+, 6), 250 (77), 249 (100), 220 (11), 91 (57); Anal.
Calcd for C25H20FNO3: C, 74.80; H, 5.02; N, 3.49%. Found: C, 74.71; H, 4.97; N,
3.44%.
23. Methyl (4-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl carbamate (Table 2,
entry 3): 1H NMR (300 MHz, DMSO-d6): d 3.57 (s, 3H), 6.84 (d, J = 8.2 Hz, 1H),
7.20–7.41 (m, 7H), 7.71–7.81 (m, 3H), 7.89 (d, J = 7.3 Hz, 1H, NH), 10.16 (s, 1H,
OH) ppm; 13C NMR (75 MHz, DMSO-d6): d 50.3, 52.1, 118.9, 123.0, 123.4, 127.1,
128.4, 128.5, 128.8, 129.1, 130.0, 131.4, 132.4, 141.9, 153.4, 157.1 ppm; IR (KBr,
cmÀ1): 3422, 3225, 2951, 1685, 1629, 1583, 1516, 1491, 1438, 1330, 1273,
1245, 1182, 1144, 1088, 1014, 963, 852, 807, 749, 708; MS (EI, 70 eV): m/z
(%) = 341 (M+, 7), 266 (33), 265 (50), 231 (100), 202 (18); Anal. Calcd for
C19H16ClNO3: C, 66.77; H, 4.72; N, 4.10%. Found: C, 66.71; H, 4.68; N, 4.10%.
24. Methyl (2,4-dichlorophenyl)(2-hydroxynaphthalen-1-yl)methyl carbamate (Table
2, entry 4): 1H NMR (300 MHz, DMSO-d6): d 3.54 (s, 3H), 6.83 (d, J = 8.1 Hz, 1H),
7.13 (d, J = 8.9 Hz, 1H), 7.28 (t, J = 7.3 Hz, 1H), 7.38–7.57 (m, 4H), 7.75 (d,
J = 8.7 Hz, 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.92 (d, J = 8.0 Hz, 1H, NH), 8.01 (d,
J = 8.6 Hz, 1H), 9.93 (s, 1H, OH) ppm; 13C NMR (75 MHz, DMSO-d6): d 49.9, 52.0,
116.8, 119.0, 122.9, 123.1, 127.0, 127.1, 128.7, 129.0, 129.1, 130.2, 131.7, 132.4,
133.0, 133.6, 139.3, 154.0, 156.6 ppm; IR (KBr, cmÀ1): 3404, 3259, 1677, 1626,
1620, 1469, 1437, 1319, 1273, 1236, 1190, 1054, 1035, 815, 853; MS (EI,
70 eV): m/z (%) = 376 (M+, 1), 375 (6), 267 (59), 266 (33), 265 (100), 231 (18),
202 (14), 115 (10), 101 (6); Anal. Calcd for C19H15Cl2NO3: C, 60.65; H, 4.02; N,
3.72%. Found: C, 60.61; H, 4.04; N, 3.75%.
25. Methyl (3-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl carbamate (Table 2,
entry 5): 1H NMR (300 MHz, DMSO-d6): d 3.58 (s, 3H), 6.86 (d, J = 8.6 Hz, 1H),
7.13–7.31 (m, 6H), 7.41 (t, J = 7.6 Hz, 1H), 7.77–7.83 (m, 3H), 7.92 (d, J = 8.0 Hz,
1H, NH), 10.19 (s, 1H, OH) ppm; 13C NMR (75 MHz, DMSO-d6): d 50.4, 52.2,
118.7, 118.9, 123.1, 123.3, 125.3, 126.2, 126.8, 127.2, 128.8, 129.1, 130.1, 130.5,
132.4, 133.3, 145.6, 153.4, 157.1 ppm; IR (KBr, cmÀ1): 3417, 3293, 3070, 1688,
1628, 1596, 1572, 1516, 1474, 1438, 1335, 1274, 1241, 1190, 1045, 808, 748;
MS (EI, 70 eV): m/z (%) = 341 (M+, 20), 265 (40), 231 (100), 202 (18), 170 (5),
115 (11), 59 (8); Anal. Calcd for C19H16ClNO3: C, 66.77; H, 4.72; N, 4.10%.
Found: C, 67.02; H, 4.75; N, 4.11%.
26. Methyl (2-hydroxynaphthalen-1-yl)(3-nitrophenyl)methyl carbamate (Table 2,
entry 6): 1H NMR (300 MHz, DMSO-d6): d 3.60 (s, 3H), 6.96 (d, J = 8.6 Hz, 1H),
7.22 (d, J = 8.9 Hz, 1H), 7.30 (t, J = 7.3 Hz, 1H), 7.43 (t, J = 7.6 Hz, 1H), 7.55 (t,
J = 7.8 Hz, 1H), 7.63 (d, J = 7.8 Hz, 1H), 7.79–7.97 (m, 4H), 8.07 (d, J = 8.0 Hz, 1H,
NH), 8.12 (s, 1H) 10.23 (s, 1H, OH) ppm; 13C NMR (75 MHz, DMSO-d6): d 50.5,
52.3, 118.3, 118.9, 121.0, 122.0, 123.0, 123.1, 127.3, 128.8, 129.1, 130.2, 130.4,
132.4, 133.3, 145.5, 148.2, 153.6, 157.2 ppm; IR (KBr, cmÀ1): 3389, 3290, 3088,
1687, 1630, 1578, 1525, 1440, 1340, 1278, 1246, 1138, 1044, 923, 806, 733,
634; MS (EI, 70 eV): m/z (%) = 352 (M+, 28), 335 (18), 295 (40), 277 (33), 276
(57), 260 (87), 231 (80), 230 (100), 202 (39), 149 (12), 115 (15); Anal. Calcd for
C19H16N2O5: C, 64.77; H, 4.58; N, 7.95%. Found: C, 64.80; H, 4.57; N, 7.92%.
27. Methyl (2,5-dimethoxyphenyl)(2-hydroxynaphthalen-1-yl)methyl carbamate
(Table 2, entry 7): 1H NMR (300 MHz, DMSO-d6): d 3.54 (s, 3H), 3.56 (s, 3H),
3.64 (s, 3H), 6.73 (d, J = 8.8 Hz, 1H), 6.81 (d, J = 8.8 Hz, 1H), 7.02 (d, J = 9.1 Hz,