KOKSAL ET AL.
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13C‐NMR (DMSO, ppm); 28.60 (piperidine, C3 + C5), 37.53 (piper-
idine, C4), 50.03 (piperidine, C2 + C6), 70.56 (N–CH2–N), 109.04
(2‐hydroxyphenyl C5), 117.02 (2‐hydroxyphenyl C4), 119.45
(2‐hydroxyphenyl C6), 128.39 (2‐hydroxyphenyl C3), 133.51
(2‐hydroxyphenyl C1), 156.35 (2‐hydroxyphenyl C2), 157.35 (ox-
adiazole C5), and 177.03 (oxadiazole C═S). Analytical calculated for
13C‐NMR (DMSO, ppm); 25.47 (CH3) 32.11 (piperidine, C3 + C5),
47.40 (piperidine, C4), 53.50 (piperidine, C2 + C6), 69.98 (N–CH2–N),
108.86 (2‐hydroxyphenyl C5), 117.03 (2‐hydroxyphenyl C4), 119.40
(2‐hydroxyphenyl C6), 126.22 (phenyl C4), 126.97 (phenyl C2 + C6),
128.75 (phenyl C3 + C5), 129.02 (2‐hydroxyphenyl C3), 133.63
(2‐hydroxyphenyl C1), 141.26 (phenyl, C1), 156.36 (2‐hydroxyphenyl
C2), 157.83 (oxadiazole C5), 176.92 (oxadiazole C═S), and 208.91
(C═O). Analytical calculated for C22H23N3O3S.HCl; Cal. C, 65.37; H,
5.76; N, 11.44; S, 8.73. Found: C, 64.64; H, 5.49; N, 11.44; S, 8.73.
C
15H19N3O3S.H2O; Cal. C, 56.06; H, 5.96; N, 13.07; S, 9.98. Found: C,
55.98; H, 6.29; N, 13.02; S, 9.90.
5‐(2‐Hydroxyphenyl)‐3‐[(4‐phenylpiperidin‐1‐yl)methyl]‐1,3,4‐
oxadiazole‐2(3H)‐thione (5c)
5‐(2‐Hydroxyphenyl)‐3‐[(4‐cyano‐4‐phenylpiperidin‐1‐yl)methyl]‐
1,3,4‐oxadiazole‐2(3H)‐thione (5f)
FT‐IR (KBr, cm−1); 3469 (OH), 2959 (CH aromatic), 2817 (CH
aliphatic), 1625 (C═N), 1592 (C═C), 1489 (C═S), and 1253 (C–N).
1H‐NMR (DMSO, ppm); 10.52 (bs, 1H, OH), 7.66 (dd,
1H, 2‐hydroxyphenyl H3, J = 8 Hz, Jʹ = 2 Hz), 7.46–7.41 (m,
1H, 2‐hydroxyphenyl H4), 7.25–7.13 (m, 5H, phenyl), 7.04 (dd, 1H,
2‐hydroxyphenyl H6, J = 8.4 Hz, Jʹ = 0.8 Hz), 6,99–6.95 (m, 1H,
2‐hydroxyphenyl H5), 5.07 (s, 2H, N–CH2–N), 3.14 (d, 2H, piperidine
H2, J = 12 Hz), 2.60 (t, 2H, piperidine H3, J = 10.4 Hz), 2.46–2.40 (m, 1H,
piperidine H4), 1.73 (d, 2H, piperidine H6, J = 10.8 Hz), and 1.67–1.58 (m,
2H, piperidine H5). 13C‐NMR (DMSO, ppm); 32.84 (piperidine, C3 + C5)
40.87 (piperidine, C4), 50.57 (piperidine, C2 + C6), 70.33 (N–CH2–N),
108.96 (2‐hydroxyphenyl C5), 117.00 (2‐hydroxyphenyl C4), 119.41
(2‐hydroxyphenyl C6), 125.92 (phenyl C4), 126.57 (phenyl C2 + C6),
128.22 (phenyl C3 + C5), 129.02 (2‐hydroxyphenyl C3), 133.57
(2‐hydroxyphenyl C1), 145.98 (phenyl, C1), 156.28 (2‐hydroxyphenyl C2),
157.85 (oxadiazole C5), and 176.96 (oxadiazole C═S). Analytical calcu-
lated for C20H21N3O2S; Cal. C, 65.37; H, 5.76; N, 11.44; S, 8.73. Found: C,
64.64; H, 5.49; N, 11.44; S, 8.73.
FT‐IR (KBr, cm−1); 3363 (OH), 2952 (CH aromatic), 2832 (CH aliphatic),
2240 (C≡N), 1625 (C═N), 1597 (C═C), 1490 (C═S), and 1253 (C–N).
1H‐NMR (DMSO, ppm); 2.06–1.99 (m, 2H, piperidine H5), 2.15 (d, 2H,
piperidine H6, J = 12.8 Hz), 2.85–2.83 (m, 2H, piperidine H3), 3.25
(d, 2H, piperidine H2, J = 12.4 Hz), 5.13 (s, 2H, N–CH2–N), 7.00 (t, 1H,
2‐hydroxyphenyl H5, J = 7.6 Hz), 7.09 (d, 1H, 2‐hydroxyphenyl H6,
J = 8.4 Hz), 7.54–7.35 (m, 5H, phenyl), 7.65 (dd, 1H, 2‐hydroxyphenyl H3,
J = 7.6 Hz, Jʹ = 1.6 Hz), and 10.61 (bs, 1H, OH). 13C‐NMR (DMSO, ppm);
35.12 (piperidine, C3 + C5), 41.29 (piperidine, C4), 47.52 (piperidine,
C2 + C6), 69.62 (N–CH2–N), 108.81 (2‐hydroxyphenyl C5), 117.06
(2‐hydroxyphenyl C4), 119.43 (2‐hydroxyphenyl C6), 121.60 (phenyl C4),
125.52 (phenyl C2 + C6), 128.00 (2‐hydroxyphenyl C3), 128.93 (phenyl
C3 + C5), 129.07 (2‐hydroxyphenyl C3), 133.74 (2‐hydroxyphenyl C1),
139.92 (phenyl, C1), 156.46 (2‐hydroxyphenyl C2), 157.98 (oxadiazole
C5), and 176.99 (oxadiazole C═S). Analytical calculated for
C20H20N4O2S.HCl; Cal. C, 64.27; H, 5.14; N, 14.28; S, 8.17. Found: C,
63.86; H, 4.86; N, 14.37; S, 8.28.
5‐(2‐Hydroxyphenyl)‐3‐[(4‐hydroxy‐4‐phenylpiperidin‐1‐yl)methyl]‐
1,3,4‐oxadiazole‐2(3H)‐thione (5d)
5‐(2‐Hydroxyphenyl)‐3‐[(4‐phenylpiperazin‐1‐yl)methyl]‐1,3,4‐
oxadiazole‐2(3H)‐thione (5g)[21]
FT‐IR (KBr, cm−1); 3335 (OH), 2954 (CH aromatic), 2829 (CH aliphatic),
1625 (C═N), 1591 (C═C), 1489 (C═S), and 1252 (C–N). 1H‐NMR
(DMSO, ppm); 1.74 (d, 2H, piperidine H6, J = 6.4 Hz), 2.32–2.20 (m, 1H,
piperidine H4), 2.50 (t, 2H, piperidine H3, J = 3.8 Hz), 3.22 (d, 2H, pi-
peridine H2, J = 7.6 Hz), 5.45 (s, 2H, N–CH2–N), 7.48–7.24 (m, 5H,
phenyl), 7.48–7.46 (m, 1H, 2‐hydroxyphenyl H4), 7.46 (d, 1H,
2‐hydroxyphenyl H3, J = 2 Hz), and 9.08 (bs, 2H, OH). Analytical
calculated for C20H21N3O3S; Cal. C, 62.64; H, 5.52; N, 10.96; S, 8.36.
Found: C, 62.71; H, 5.78; N, 10.45; S, 8.41.
FT‐IR (KBr, cm−1); 3332 (OH), 2886 (CH aromatic), 2830 (CH ali-
phatic), 1626 (C═N), 1598 (C═C), 1489 (C═S), and 1223 (C–N).
1H‐NMR (DMSO, ppm); 2.90 (t, 4H, piperazine H2 + H6, J = 4.8 Hz),
3.13 (t, 4H, piperazine H3 + H5, J = 4.8 Hz), 5.1 (s, 2H, N–CH2–N),
6.76 (t, 1H, phenyl H4, J = 7.2 Hz), 6.90 (bd, 2H, phenyl H2 + H6,
J = 8.0 Hz), 6.95–6.99 (m, 1H, 2‐hydroxyphenyl H5), 7.05 (bd, 1H,
2‐hydroxyphenyl H6, J = 8.4 Hz), 7.18 (t, 2H, phenyl H3 + H5,
J = 7.8 Hz), 7.42–7.46 (m, 1H, 2‐hydroxyphenyl H4), 7.66 (dd, 1H,
2‐hydroxyphenyl H3, J = 8 Hz, Jʹ = 1.6 Hz), and 10.51 (bs, 1H, OH).
5‐(2‐Hydroxyphenyl)‐3‐[(4‐acetyl‐4‐phenylpiperidin‐1‐yl)methyl]‐
1,3,4‐oxadiazole‐2(3H)‐thione (5e)
5‐(2‐Hydroxyphenyl)‐3‐[(4‐(2‐pyridyl)phenylpiperazin‐1‐yl)methyl]‐
1,3,4‐oxadiazole‐2(3H)‐thione (5h)[21]
FT‐IR (KBr, cm−1); 3372 (OH), 2963 (CH aromatic), 2830 (CH ali-
phatic), 1799 (C═O), 1630 (C═N), 1596 (C═C), 1490 (C═S), and
1259 (C–N). 1H‐NMR (DMSO, ppm); 1.84 (s, 3H, CH3), 1.99–1.93 (m,
2H, piperidine H5), 2.43 (d, 2H, piperidine H6, J = 14 Hz), 2.64 (t, 2H,
piperidine H3, J = 9.6 Hz), 2.94–2.91 (m, 2H, piperidine H2), 5.00
(s, 2H, N–CH2–N), 6,99–6.96 (m, 1H, 2‐hydroxyphenyl H5), 7.06
(d, 1H, 2‐hydroxyphenyl H6, J = 8 Hz), 7.56–7.43 (m, 1H,
2‐hydroxyphenyl H4), 7.47–7.24 (m, 5H, phenyl), 7.61 (dd, 1H,
2‐hydroxyphenyl H3, J = 8 Hz, Jʹ = 1 Hz), and 10.56 (bs, 1H, OH).
FT‐IR (KBr, cm‐1); 3435 (OH), 3012 (CH aromatic), 1612 (C═N),
1603, 1560 (C═C), 1484 (C═S), and 1264 (C–N). 1H‐NMR (DMSO,
ppm); 2.48 (t, 4H, piperazine H2 + H6, J = 5 Hz), 3.48 (t, 4H, piperazine
H3 + H5, J = 5 Hz), 5.08 (s, 2H, N–CH2–N), 6.60–6.57 (m, 1H, pyridyl
H5), 6.79 (t, 1H, pyridyl H6, J = 8.8 Hz), 6.93–6.79 (m, 1H, phenyl H5),
7.01 (d, 1H, phenyl H6, J = 8 Hz), 7.44–7.40 (m, 1H, phenyl H4),
7.50–7.46 (m, 1H, 2‐hydroxyphenyl H4), 7.63 (dd, 1H,
2‐hydroxyphenyl H6, J = 8 Hz, Jʹ = 1.6 Hz), 8.05 (dd, 1H,
2‐hydroxyphenyl H3, J = 4Hz, Jʹ = 2 Hz), and 10.51 (bs, 1H, OH).