Original Article
Thieme
2
-[(5-[(3-Methoxyphenoxy)methyl]-1,3,4-oxadiazol-2-
1
ing), 1263–1037 (C–O stretching). H-NMR (400MHz, DMSO-d ,
6
yl)thio]-1-(4-methoxyphenyl)ethan-1-one (6c)
ppm) δ 3.71 (3H, s, OCH ), 5.17 (2H, s, CO-CH ), 5.34 (2H, s, OCH ),
3
2
2
Yield 72%, m.p. 110°C. IR (KBr, cm− 1): νmax 3094–3027 (aromatic
C–H), 2 999–2 875 (aliphatic C–H), 1 666 (C = O stretching),
6.54–6.61 (3H, m, Ar-H), 7.16–7.20 (1H, m, Ar-H), 8.24 (2H, d,
J = 9.2 Hz, Ar-H), 8.36 (2H, d, J= 9.2 Hz, Ar-H). 13C-NMR (100 MHz,
DMSO-d , ppm) δ 40.69 (S-CH ), 55.14 (OCH ), 59.35 (OCH ),
1
587–1456 (C=N and C=C stretching), 1269–1006 (C–O stretch-
6
2
3
2
1
ing). H-NMR (400MHz, DMSO-d , ppm) δ 3.71 (3H, s, OCH ), 3.84
101.17, 106.82, 107.49, 123.92, 129.87, 130.10, 139.62, 150.27,
6
3
(
3H, s, Ar- OCH ), 5.05 (2H, s, CO-CH ), 5.34 (2H, s, OCH ), 6.55–
158.37, 160.47, 163.72, 164.16, 191.79 (C =O). For C18H15N O S
3
2
2
3
6
6
.61 (3H, m, Ar-H), 7.07 (2H, d, J=8.8Hz, Ar-H), 7.16–7.21 (1H, m,
calculated: 53.86% C, 3.77% H, 10.47% N, 23.92% O, 7.99% S; found:
53.75 % C, 3.78 % H, 10.43 % N, 23.85 % O, 8.01 % S. HRMS (m/z):
Ar-H), 8.00 (2H, d, J=9.2Hz, Ar-H). 13C-NMR (100MHz, DMSO-d6,
+
ppm) δ 40.38 (S-CH ), 55.16, 55.65, 59.36 (OCH ), 101.18, 106.86,
[M+H] calcd for C H N O S: 402.0754; found 402.0746.
2
2
18 15
3
6
1
1
07.51, 114.09, 127.82, 130.10, 130.87, 158.39, 160.49, 163.55,
N-(Benzothiazol-2-yl)-2-[(5-[(3-methoxyphenoxy)
methyl]-1,3,4-oxadiazol-2-yl)thio]acetamide (7a)
Yield 75%, m.p. 180°C. IR (KBr, cm− 1): νmax 3394 (N–H stretching),
63.75, 164.54, 190.52 (C=O). For C H N O S calculated: 59.06%
19
18
2
5
C, 4.69% H, 7.25% N, 20.70% O, 8.30% S; found: 59.01% C, 4.69%
H, 7.26 % N, 20.75 % O, 8.32 % S. HRMS (m/z): [M + H]+ calcd for
C H N O S: 387.1009; found 387.0999.
3 145–3 010 (aromatic C–H), 2 958–2 883 (aliphatic C–H), 1 685
19
18
2
5
(
1
C = O stretching), 1 597–1 473 (C = N and C = C stretching),
261–1 012 (C–O and C–N stretching). H-NMR (400 MHz, DM-
1
-(4-Chlorophenyl)-2-[(5-[(3-methoxyphenoxy)
1
methyl]-1,3,4-oxadiazol-2-yl)thio]ethan-1-one (6d)
SO-d , ppm) δ 3.70 (3H, s, OCH ), 4.46 (2H, s, CO-CH ), 5.36 (2H, s,
6
3
2
Yield 70%, m.p. 100°C. IR (KBr, cm− 1): νmax 3093–3003 (aromatic
OCH ), 6.54–6.61 (3H, m, Ar-H), 7.18 (1H, t, J=6.4Hz, Ar-H), 7.29
2
C–H), 2 947–2 883 (aliphatic C–H), 1 676 (C = O stretching),
(1H, t, J=6.8Hz), 7.42 (1H, t, J=7.6Hz, Ar-H), 7.74 (1H, d, J=8, Ar-
H), 7.95 (1H, d, J=7.6Hz, Ar-H) 12.75 (1H, s, NH). 13C-NMR (100MHz,
DMSO-d , ppm) δ 35.87 (S-CH ), 55.14 (OCH ), 59.40 (OCH ),
1
610–1467 (C=N and C=C stretching), 1261–1031 (C–O stretch-
1
ing). H-NMR (400MHz, DMSO-d , ppm) δ 3.71 (3H, s, OCH ), 5.10
6
3
6
2
3
2
(
7
2H, s, CO-CH ), 5.34 (2H, s, OCH ), 6.39–6.61 (2H, m, Ar-H), 7.18–
.23 (1H, m, Ar-H), 7.58 (2H, t, J=7.8Hz, Ar-H), 7.71 (1H, t, J=7.4Hz,
101.16, 106.82, 107.50, 120.58, 121.70, 123.59, 126.12, 130.08,
131.50, 148.49, 158.12, 158.39, 160.49, 163.78, 164.26, 166.40
(C=O). For C H N O S calculated: 53.26% C, 3.76% H, 13.08% N,
2
2
Ar-H), 8.04 (2H, d, J=7.2Hz, Ar-H). 13C-NMR (100MHz, DMSO-d6,
19
16
4
4 2
ppm) δ 40.45 (S-CH ), 55.07 and 55.16 (OCH ), 59.36 and 66.08
14.94% O, 14.97% S; found: 53.38% C, 3.75% H, 13.04% N, 14.98%
2
3
+
(
OCH ), 97.42, 101.02, 101.18, 106.79 and 106.85, 107.23, 107.51,
O, 14.93% S. HRMS (m/z): [M+H] calcd for C H N O S : 429.068;
2
19 16
4
4 2
1
1
1
28.19, 128.63, 129.01, 129.32, 129.97, 130.11, 130.34, 133.69,
33.97, 135.50, 138.94, 158.39 and 158.53, 160.36 and 160.49,
63.66, 164.33, 167.67, 169.13, 191.42 (C=O). For C H ClN O S
found 429.0674.
N-(6-Methylbenzothiazol-2-yl)-2-[(5-[(3-methoxyphe-
noxy)methyl]-1,3,4-oxadiazol-2-yl)thio]- acetamide
18
15
2
4
calculated: 55.31% C, 3.87% H, 9.07% Cl, 7.17% N, 16.37% O, 8.20%
S; found: 55.41% C, 3.86% H, 9.05% Cl, 7.18% N, 16.35% O, 8.18%
S. HRMS (m/z): [M+H] calcd for C H ClN O S: 391.0514; found
(7b)
+
Yield 64%, m.p. 212°C. IR (KBr, cm− 1): νmax 3476 (N–H stretching),
3 094–3 002 (aromatic C–H), 2 972–2 876 (aliphatic C–H), 1 689
18
15
2
4
391.0504.
(
1
C = O stretching), 1 593–1 462 (C = N and C = C stretching),
261–1 049 (C–O and C–N stretching). H-NMR (400 MHz, DM-
1
-(4-Fluorophenyl)-2-[(5-[(3-methoxyphenoxy)
1
methyl]-1,3,4-oxadiazol-2-yl)thio]ethan-1-one (6e)
SO-d , ppm) δ 2.41 (3H, s, Ar-CH ), 3.72 (3H, s, OCH ), 4.44 (2H, s,
6
3
3
Yield 73%, m.p. 126°C. IR (KBr, cm− 1): νmax 3107–3029 (aromatic
CO-CH ), 5.36 (2H, s, OCH ), 6.56–6.62 (3H, m, Ar-H), 7.19 (1H, t,
2 2
C–H), 2 968–2 838 (aliphatic C–H), 1 674 (C = O stretching),
J=7.6Hz, Ar-H), 7.27 and 7. 25 (1H, dd, J1=1.2Hz, J2=1.2Hz, Ar-H),
7.65 (1H, d, J=8.4Hz, Ar-H), 7.77 (1H, s, Ar-H), 12.69 (1H, s, NH).
1
595–1473 (C=N and C=C stretching), 1261–1026 (C–O stretch-
1
13
ing). H-NMR (400MHz, DMSO-d , ppm) δ 3.73 (3H, s, OCH ), 5.12
C-NMR (100MHz, DMSO-d , ppm) δ 20.96 (CH ), 35.65 (S-CH ),
6
3
6
3
2
(
2H, s, CO-CH ), 5.36 (2H, s, OCH2), 6.57–6.63 (3H, m, Ar-H), 7.19–
55.14 (OCH ), 59.40 (OCH ), 101.16, 106.82, 107.51, 120.58,
3 2
2
7
.23 (1H, m, Ar-H), 7.39–7.44 (2H, m, Ar-H), 8.11–8.15 (2H, m, Ar-
120.31, 121.33, 127.53, 130.09, 131.58, 133.23, 156.74, 158.38,
H). 13 C-NMR (100 MHz, DMSO-d , ppm) δ 40.43 (S-CH ), 55.15
160.48, 163.80, 164.17, 166.01 (C=O). For C H N O S calculat-
6
2
20 18
4
4 2
(
(
1
1
5
5
OCH ), 59.35 (OCH ), 101.17, 106.85, 107.50, 115.85 and 116.07
J = 22.1 Hz), 130.10, 131.50 and 131.59 (J = 9 Hz), 131.75 and
31.77 (J=2Hz), 158.38, 160.49, 163.63, 164.17, 164.36, 166.68,
ed: 54.28 % C, 4.10 % H, 12.66 % N, 14.46 % O, 14.49 % S; found:
54.36% C, 4.10% H, 12.68% N, 14.41% O, 14.45% S. HRMS (m/z):
3
2
+
[M+H] calcd for C H N O S : 443.0842; found 443.0836.
20
18
4
4 2
90.94 (C= O). For C18H15FN O S calculated: 57.75% C, 4.04 % H,
2
4
N-(6-Methoxybenzothiazol-2-yl)-2-[(5-[(3-methoxy-
phenoxy)methyl]-1,3,4-oxadiazol-2-yl)thio]acetamide
.07% F, 7.48% N, 17.09% O, 8.56% S; found: 57.60% C, 4.03% H,
+
.08% F, 7.49% N, 17.04% O, 8.57% S. HRMS (m/z): [M+H] calcd
(7c)
for C H FN O S: 375.0809; found 375.0795.
18
15
2
4
Yield 76%, m.p. 212°C. IR (KBr, cm− 1): νmax 3459 (N–H stretching),
093–3 019 (aromatic C–H), 2 987–2 849 (aliphatic C–H), 1 689
2
-[(5-[(3-Methoxyphenoxy)methyl]-1,3,4-oxadiazol-2-
3
yl)thio]-1-(4-nitrophenyl)ethan-1-one (6f)
Yield 68 %, m.p. 93 °C. IR (KBr, cm− 1): νmax 3 105–3 013 (aromatic
(
C = O stretching), 1 610–1 467 (C = N and C = C stretching),
1
1 261–1 028 (C–O and C–N stretching). H-NMR (400 MHz, DM-
SO-d , ppm) δ 3.72 (3H, s, OCH ), 3.80 (3H, s, Ar-CH ), 4.44 (2H, s,
C–H), 2 974–2 846 (aliphatic C–H), 1 683 (C = O stretching),
6
3
3
1
602–1471 (C=N and C=C stretching), 1527–1344 (NO stretch-
CO-CH ), 5.36 (2H, s, OCH ), 6.56–6.61 (3H, m, Ar-H), 7.03 and 7.05
2
2
2
Kaya B et al. Novel 1,3,4-Oxadiazole Derivatives … Drug Res