Helvetica Chimica Acta – Vol. 90 (2007)
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(D6)DMSO): 168.37; 152.90; 132.22; 128.17; 125.90; 122.41; 122.06; 119.73; 118.48; 45.81; 33.62; 31.04;
25.89; 22.63; 21.93; 13.73. EI-MS: 285 (Mþ), 215, 184, 173, 116, 44.
N-[(2-Hydroxynaphthalen-1-yl)(3-methoxyphenyl)methyl]benzamide (1k). IR (KBr): 3381, 1641,
1572, 1515, 1398, 1111, 693. 1H-NMR (200 MHz, (D6)DMSO): 9.87( s, 1 H); 8.82 (d, J ¼ 8.6, 1 H); 8.16 (d,
J ¼ 8.6, 1 H); 7.91 – 6.82 (m, 14 H); 6.65 (d, J ¼ 7.8, 1 H); 3.71 (s, 3 H). 13C-NMR (75 MHz, (D6)DMSO):
168.03; 165.79; 159.19; 153.14; 143.62; 134.28; 134.20; 132.28; 131.43; 131.20; 129.37; 129.28; 128.49;
128.35; 128.17; 127.42; 127.07; 126.77; 122.68; 118.81; 118.66; 118.25; 112.96; 54.86; 49.22. LC/MS: 406
([M þ Na]þ), 383 (Mþ).
1-[1-(2-Hydroxynaphthalen-1-yl)propyl]thiourea (1m). IR (KBr): 3413, 1626, 1545, 1514, 1265, 811,
750. 1H-NMR (200 MHz, (D6)DMSO): 9.80 (s, 1 H); 8.35 – 7.10 (m, 8 H); 6.33 (br., 2 H); 2.18 – 2.08 (m,
2 H); 0.83 (t, J ¼ 7.3, 3 H). LC/MS: 283 ([M þ Na]þ).
1-[(2-Hydroxynaphthalen-1-yl)(pyridin-4-yl)methyl]urea (1s). IR (KBr): 3405, 1615, 1510, 1135,
784. 1H-NMR (200 MHz, (D6)DMSO): 9.70 (s, 1 H); 8.41 (d, J ¼ 5.9, 2 H); 7.93 – 7.10 (m, 8 H); 6.70 (s,
1 H); 6.48 (s, 1 H). 13C-NMR (75 MHz, (D6)DMSO): 154.44; 152.32; 149.12; 131.99; 129.31; 128.70;
128.15; 125.43; 124.85; 122.27; 120.64; 120.23; 117.99; 65.66. LC/MS: 316 ([M þ Na]þ).
N-[(2-Hydroxynaphthalen-1-yl)(phenyl)methyl]ethanethioamide (1u). IR (KBr): 3420, 1628, 1514,
1
1441, 1379, 1267, 1212, 1170, 811, 747. H-NMR (200 MHz, (D6)DMSO): 9.82 (s, 1 H); 8.19 – 7.11 (m,
13 H); 2.62 (s, 3 H). 13C-NMR (75 MHz, (D6)DMSO): 199.51; 153.51; 140.25; 132.57; 129.57; 128.44;
128.17; 128.00; 126.51; 126.25; 122.70; 122.41; 118.43; 116.89; 55.33; 32.90. LC/MS: 330 ([M þ Na]þ).
N-[1-(1-Hydroxynaphthalen-2-yl)propyl]acetamide (2w). IR (KBr): 3390, 1617, 1575, 1540, 1460,
1377, 1079, 807. 1H-NMR (300 MHz, CDCl3): 9.95 (s, 1 H); 8.35 (d, J ¼ 7.8, 1 H); 7.68 (d, J ¼ 7.8, 1 H); 7.40
(m, 2 H); 7.28 (d, J ¼ 8.5, 1 H); 7.12 (d, J ¼ 8.5, 1 H); 6.08 (d, J ¼ 8.6, 1 H); 5.08 (q, J ¼ 7.7, 1 H); 2.01 (m,
2 H); 1.95 (s, 3 H); 0.98 (t, J ¼ 7.4, 3 H). LC/MS: 266 ([M þ Na]þ).
N-[1-(4-Hydroxynaphthalen-1-yl)propyl]acetamide (3w). IR (KBr): 3401, 3275, 1644, 1583, 1542,
1384, 1276, 1054, 764. 1H-NMR (200 MHz, (D6)DMSO): 9.59 (s, 1 H); 8.22 (d, J ¼ 7.8, 1 H); 8.05 (d, J ¼
7.8, 1 H); 7.72 (d, J ¼ 8.6, 1 H); 7.52 – 7.20 (m, 3 H); 6.80 (d, J ¼ 8.6, 1 H); 5.50 (q, J ¼ 7.8, 1 H); 2.02 – 1.85
(m, 5 H); 0.95 (t, J ¼ 7.8, 3 H). 13C-NMR (75 MHz, (D6)DMSO): 169.25; 152.38; 132.10; 129.60; 126.49;
124.95; 124.45; 123.69; 123.14; 122.79; 107.55; 50.79; 49.65; 22.75; 11.15. LC/MS: 266 ([M þ Na]þ).
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