Molecules 2017, 22, 1381
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6.96–7.05 (6H, m, monosubstituted benzene H2,2’, disubstituted benzene CH, methoxyphenyl CH),
7.20 (2H, t, J = 8.10 Hz, monosubstituted benzene H3,3’), 7.61 (2H, d, J = 8.67 Hz, Disubstituted benzene
CH), 7.83 (1H, s, -CH=N-), 10.23 (1H, s, NH). 13C-NMR:
δ = 55.89, 112.33, 115.58, 117.87, 118.98,
121.29, 127.67, 129.54, 130.89, 136.49, 145.87, 149.60, 156.22, 158.40. HRMS (m/z): [M + H]+ calcd for
C20H18N2O2: 319.1441; found: 319.1448
1-(4-((4-Methoxyphenyl)thio)benzylidene)-2-phenylhydrazine (2f). Yield: 85%, M.P. = 178.1–184.3 ◦C,
1
FTIR (ATR, cm−1): 3300 (N-H), 2956 (C-H), 1244 (C-N), 815, 742. H-NMR:
δ = 3.79 (3H, s, -OCH3),
6.74 (1H, t, J = 7.26 Hz, monosubstituted benzene H4), 6.99–7.06 (4H, m, monosubstituted
benzene H2,2’, disubstituted benzene CH), 7.13 (2H, d, J = 8.43 Hz, methoxyphenyl CH), 7.20
(
2H, t, J = 7.32 Hz, monosubstituted benzene H3,3’), 7.43 (2H, d, J = 8.85 Hz, disubstituted benzene
CH), 7.56 (2H, d, J = 8.46 Hz, methoxyphenyl CH), 7.80 (1H, s, -CH=N-), 10.33 (1H, s, NH). 13C-NMR:
δ
= 55.80, 112.44, 115.87, 119.24, 123.42, 126.79, 128.50, 129.56, 134.28, 135.64, 136.14, 137.73, 145.64,
160.19. HRMS (m/z): [M + H]+ calcd for C20H18N2OS: 335.1213; found: 335.1207.
1-(4-(4-Fluorophenoxy)benzylidene)-2-phenylhydrazine (2g). Yield: 81%, M.P. = 121.3–124.9 ◦C, FTIR
(ATR, cm−1): 3315 (N-H), 2951 (C-H), 1251 (C-N), 821, 752. 1H-NMR:
δ
= 6.73 (1H, t, J = 7.23 Hz,
monosubstituted benzene H4), 6.99 (2H, d, J = 8.73 Hz, monosubstituted benzene H2,2’), 7.03–7.12 (4H,
m, disubstituted benzene CH, fluorophenyl CH), 7.18–7.28 (4H, m, monosubstituted benzene H3,3’
fluorophenyl CH), 7.65 (2H, d, J = 8.76 Hz, disubstituted benzene CH), 7.85 (1H, s, -CH=N-), 10.27 (1H,
,
s, NH). 13C-NMR: = 112.36, 116.94, 117.25, 118.88 (2JCF = 26.34 Hz), 121.28 (3JCF = 8.54 Hz), 127.76,
δ
129.55, 131.62, 136.30, 145.82, 152.82, 157.42, 158.78 (1JCF = 238.19 Hz). HRMS (m/z): [M + H]+ calcd for
C19H15FN2O: 307.1241; found: 307.1235.
1-(4-((4-Fluorophenyl)thio)benzylidene)-2-phenylhydrazine (2h). Yield: 80%, M.P. = 132.3–133.9 ◦C,
1
FTIR (ATR, cm−1): 3325 (N-H), 2958 (C-H), 1257 (C-N), 831, 752. H-NMR:
δ = 6.75 (1H, t, J = 7.23 Hz,
monosubstituted benzene H4), 7.06 (2H, d, J = 8.00 Hz, monosubstituted benzene H2,2’), 7.20
2H, d, J = 7.32 Hz, disubstituted benzene CH), 7.23–7.29 (4H, m, monosubstituted benzene H3,3’,
fluorophenyl CH), 7.42–7.47 (2H, m, fluorophenyl CH), 7.62 (2H, d, J = 8.00 Hz, disubstituted benzene
(
CH), 7.82 (1H, s, -CH=N-), 10.40 (1H, s, NH). 13C-NMR:
δ = 112.49, 117.08, 117.32, 119.36, 126.99, 129.59,
130.42 (2JCF = 26.74 Hz), 134.33 (3JCF = 8.34 Hz), 135.20, 135.34, 135.87, 145.56, 162.29 (1JCF = 244.11 Hz).
HRMS (m/z): [M + H]+ calcd for C19H15FN2S: 323.1013; found: 323.1001.
◦
1-(4-(1-Imidazolyl)benzylidene)-2-phenylhydrazine (2i). Yield: 85%, M.P. = 201.9–208.9 C, FTIR
(ATR, cm−1): 3350 (N-H), 2951 (C-H), 1269 (C-N), 906, 759. 1H-NMR:
δ
= 6.77 (1H, t, J = 7.17 Hz
monosubstituted benzene H4), 7.12 (2H, d, J = 7.50 Hz, monosubstituted benzene H3,3’), 7.22
2H, t, J = 7.29 Hz, monosubstituted benzene H2,2’), 7.54 (1H, s, imidazole CH), 7.75 (2H, d, J = 8.76 Hz,
disubstituted benzene CH), 7.82 (2H, d, J = 8.76 Hz, disubstituted benzene CH), 7.95 (1H, s, -CH=N-)
,
(
8.07 (1H, m, imidazole CH), 9.08 (1H, s, imidazole CH), 10.68 (1H, s, NH). 13C-NMR:
δ = 112.61, 119.48,
119.80, 121.84, 125.67, 127.19, 129.59, 135.26, 135.33, 135.38, 136.33, 145.55. HRMS (m/z): [M + H]+ calcd
for C16H14N4: 263.1291; found: 263.1295.
1-(4-(1H-1,2,4-triazole-1-yl)benzylidene)-2-phenylhydrazine (2j). Yield: 79%, M.P. = 127.4–132.2 ◦C,
1
FTIR (ATR, cm−1): 3319 (N-H), 2951 (C-H), 1228 (C-N), 829, 756. H-NMR:
δ = 6.77 (1H, t, J = 7.23 Hz,
monosubstituted benzene H4), 7.10 (2H, d, J = 7.53 Hz, monosubstituted benzene H3,3’), 7.23
2H, t, J = 7.26 Hz, monosubstituted benzene H2,2’), 7.26 (1H, s, triazole CH), 7.81 (2H, d, J = 8.76 Hz,
disubstituted benzene CH), 7.88 (2H, d, J = 9.15 Hz, disubstituted benzene CH), 8.25 (1H, s, -CH=N-),
(
9.33 (1H, s, triazole CH), 10.47 (1H, s, NH). 13C-NMR:
δ =112.61, 119.48, 119.80, 121.84, 125.67,
127.19, 129.59, 135.26, 135.38, 136.33, 145.55. HRMS (m/z): [M + H]+ calcd for C15H13N5: 264.1244;
found: 264.1230.
1-(4-((4-Chlorophenyl)thio)benzylidene)-2-phenylhydrazine (2k). Yield: 85%, M.P. = 164.4–165.7 ◦C,
1
FTIR (ATR, cm−1): 3223 (N-H), 2912 (C-H), 1255 (C-N), 827, 744. H-NMR:
δ = 6.76 (1H, t, J = 7.26 Hz,
monosubstituted benzene H4), 7.07 (2H, d, J = 7.59 Hz, monosubstituted benzene H2,2’), 7.19–7.24