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1
[
23] Spectral data of principal compounds: (2-Hydroxynaphthalen-1-yl)-phenylmethylurea (4a): H NMR (400 MHz, DMSO-d
6
): d 10.30 (s, 1H),
: C 73.96, H 5.52, N 9.58;
found: C 73.51, H 5.55, N 9.60. (4-Chlorophenyl)-(2-hydroxynaphthelene-1-yl)-methylurea (4b): H NMR (400 MHz, DMSO-d ): d 10.31 (s,
7
.84–7.14 (m, 12H), 6.89 (s, 2H), 5.72 (s, 2H); Mass (ES/MS): m/z 291 (MÀH, 100%); Anal. calcd. for C18
16 2 2
H N O
1
6
1
H), 7.93–7.74 (m, 3H, Ar–H), 7.52–7.13 (m, 7H, Ar–H), 6.80 (s, 2H), 5.85 (s, 2H); Mass (ES/MS): m/z 325 (MÀH, 100%); Anal. calcd. for
1
C
18
H
2
15ClN O
2
: C 66.16, H 4.63, N 8.57; found: C 66.20, H 4.58, N 8.62. (3Nitrophenyl)-(2-hydroxynaphthalen-1-yl)-methylurea (4d): H
): d 10.28 (s, 1H), 8.04–7.92 (m, 2H), 7.54–6.87 (m, 8H), 6.75 (bs, 2H), 5.83 (s, 2H); Mass (ES/MS): m/z 336
MÀH, 100%); Anal. calcd. for C18 : C 64.09, H 4.48, N 12.46; found C 64.37, H 4.53, N 12.52. N-(4-Bromophenyl)(2-
hydroxynaphthalen-1-yl)-methylacetamide (4f): H NMR (400 MHz, DMSO-d
J = 11.3 Hz, 1H), 7.80–7.66 (m, 2H), 7.42–7.05 (m, 8H), 2.02 (s, 3H); Anal. calcd. for C19
C, 61.76; H, 4.40; N, 3.62. N-((4-fluorophenyl)(2-hydroxynaphthalen-1-yl)-methyl)benzamide (4i): H NMR (300 MHz, DMSO-d
NMR (400 MHz, DMSO-d
6
(
15 3 4
H N O
1
6
): d 9.84 (s, 1H), 8.11 (d, J = 8.1 Hz, 1H), 7.92 (d,
16BrNO : C, 61.64; H, 4.36; N, 3.78; found:
): d 10.36 (s,
: C, 77.61; H, 4.88; N, 3.77; F, 5.12; found: C, 77.52; H, 4.90; N,
.76; F, 5.10. 1-(2-Hydroxynaphthalen-1-yl)-propylurea (4j): H NMR (400 MHz, DMSO-d ): d 10.37 (s, 1H), 7.66–6.97 (m, 6H), 6.45 (bs,
H
2
1
6
1
3
1
6
H), 9.37 (d, J = 9 Hz, 1H), 8.08–7.06 (m, 16H); Anal. calcd. for C24H18FNO
2
1
6
H), 5.64 (bs, 2H), 4.86 (m, 1H), 1.74 (m, 2H), 1.05 (t, 3H); Mass (ES/MS): m/z 243 (MÀH, 100%); Anal. calcd. for C14
16 2 2
H N O : C 68.83, H
.60, N 11.47; found C 69.11, H 6.62, N 11.54.