NOVEL THIOAMIDOALKYL NAPHTHOLS
523
Entry 3. 1H NMR (100 MHz, DMSO-d6): 10.08 (br, 1H), 8.30 (s, 1H),
8.05–7.90 (m, 4H), 7.70–7.60 (m, 4H), 7.40–7.25 (m, 5H), 6.75 (s, 1H); IR (KBr,
cmꢁ1): 3369, 3262, 3162, 1598, 1468, 1421 (C S), 1087 (C S), 740. Anal. calcd.
for C19H16N2O3S: C, 64.76; H, 4.58; N, 7.95; O, 13.62; S, 9.10. Found: C, 64.72;
H, 4.69; N, 8.05; S, 9.17.
=
=
Entry 4. 1H NMR (100 MHz, DMSO-d6): 10.12 (br, 1H), 8.15 (s, 1H),
7.95–7.80 (m, 3H), 7.75–7.60 (m, 4H), 7.40–7.25 (m, 6H), 6.55 (s, 1H), 3.55 (s,
3H); IR (KBr, cmꢁ1): 3292, 3085, 2647, 1480 (C S), 1381(C S), 970. Anal. calcd.
for C20H19NO2S: C, 71.19; H, 5.68; N, 4.15; O, 9.48; S, 9.50. Found: C, 71.25; H,
5.74; N, 4.08; S, 9.54.
=
=
Entry 5. 1H NMR (100 Hz, DMSO-d6): d 10.25 (br, 1H), 8.25–8.15 (m, 2H),
7.95–7.80 (m, 3H), 7.40–7.25 (m, 10H); IR (KBr, cmꢁ1): 3442, 3310, 1614, 1514,
=
1435 (C S), 1262 (C S), 1173, 811. Anal. calcd. for C18H16N2OS: C, 70.10; H,
=
5.23; N, 9.08; S, 10.40. Found: C, 69.98; H, 5.16; N, 9.03; S, 10.54.
Entry 6. 1H NMR (100 Hz, DMSO-d6): d 10.12 (br, 1H), 8.35–8.30 (ss, 1H),
8.10 (s, 1H), 7.85–7.74 (m, 4H), 7.50–7.10 (m, 8H); IR (KBr, cmꢁ1): 3471, 3285,
=
1605, 1515, 1436 (C S), 1260 (C S), 1144, 807; Anal. calcd. for C18H15ClN2OS:
=
C, 63.06; H, 4.41; N, 8.17, S; 9.35. Found: C, 63.18; H, 4.49; N, 8.28, S; 9.31.
Entry 7. 1H NMR (100 MHz, DMSO-d6): 10.10 (br, 1H), 8.35–8.30 (m, 3H),
7.90–7.75 (m, 2H), 7.50–7.25 (m, 9H), 7.05-6.95 (m, 1H), 2.30 (s, 3H); IR (KBr,
cmꢁ1): 3390, 3149, 1602, 1557, 1386 (C S), 1081 (C S), 883. Anal. calcd. for
C18H15N3O3S: C, 61.18; H, 4.28; N, 11.89; S, 9.07. Found: C, 61.22; H, 4.34; N,
11.95; S, 9.11.
=
=
Entry 8. 1H NMR (100 MHz, DMSO-d6): 11.10 (br, 1H), 8.45–8.40 (ss, 1H),
8.10–7.95 (m, 2H), 7.70–7.60 (m, 6H), 7.30–7.25 (m, 1H), 7.05-6.95 (m, 4H), 3.70 (s,
3H); IR (KBr, cmꢁ1): 3455, 3262, 2054, 1642, 1379 (C S), 1141 (C S), 814. Anal.
calcd. for C19H18N2O2S: C, 67.43; H, 5.36; N, 8.28; S, 9.47. Found: C, 67.40; H,
5.41; N, 8.20; S, 9.52.
=
=
Entry 9. 1H NMR (100 MHz, DMSO-d6): 9.95 (br, 1H), 8.45–8.30 (m, 2H),
7.70–7.60 (m, 3H), 7.30–7.10 (m, 3H), 6.75-6.60 (m, 6H), 3.65 (s, 3H); IR (KBr,
cmꢁ1): 3351, 3231, 1577, 1491, 1413 (C S), 1037 (C S), 865. Anal. calcd. for
C19H18N2O3S: C, 64.39; H, 5.12; N, 7.90; S, 9.05. Found: C, 64.47; H, 5.19; N,
7.97; S, 8.95.
=
=
Entry 10. 1H NMR (500 MHz, DMSO-d6): 10.28 (b, 3H), 7.91 (d, 0.13H, non-
bonded free-NH), 7.90 (dd, 1H, J1 ¼ 7.5 Hz, J2 ¼ 1.5 Hz), 7.76 (dt, 1H, J1 ¼ 7.5 Hz,
J2 ¼ 1.5 Hz), 7.53 (dd, 1H, J1 ¼ 7.5 Hz, J2 ¼ 1.5 Hz), 7.40 (t, 1H, J ¼ 8 Hz), 7.30 (m,
2H), 6.8–7.2 (m, 4H), 3.63 (s, 3H), 2.25 (s, 3H). IR (KBr, cmꢁ1): 3369, 3262,
=
=
3162, 1598, 1468, 1421 (C S), 1087 (C S), 740. Anal. calcd. for C20H19NO3S: C,
67.97; H, 5.42; N, 3.96; S, 9.07. Found: C, 67.92; H, 5.39; N, 4.01; S, 9.01.
1
Entry 11. 1H NMR (500 MHz, DMSO-d6): H NMR (500 MHz, DMSO-d6):
10.88 (b, 2H, OH), 7.91 (d, 1H, J ¼ 7.5 Hz), 7.78 (m, 1H), 7.61 (m, 1H), 7.53 (d, 1H,
J ¼ 7.5 Hz), 7.44 (t, 1H, J ¼ 9 Hz), 7.37 (t, 1H, J ¼ 8.5 Hz), 7.27 (m, 2H), 7.18 (m,
2H), 7.08 (m, 4H), 2.26 (s, 3H). IR (KBr, Cmꢁ1): 3359, 1629, 1525, 1474, 1420