Novel compounds containing1,3,4-‐oxadiazole…
209
h. IR(KBr) Spectral data(ν
max
incm
-‐1
)
VII
a: 3206 (NH), 1685 (C=O), 1620 (C=N)
VII
b: 3195 (NH), 1690(C=O), 1622 (C=N)
VII
c: 3230 (NH), 1685 (C=O),1625 (C=N)
VII
d: 3215 (NH), 1695(C=O), 1624(C=N)
VII
e: 3230(NH), 1675(C=O), 1630(C=N)
VII
f: 3210 (NH), 1685 (C=O), 1627 (C=N)
VII
g: 3180 (NH), 1695 (C=O), 1627 (C=N)
VII
h: 3195 (NH), 1700(C=O), 1629 (C=N)
VII
i: 3245(NH), 1705(C=O), 1630(C=N)
VII
j: 3240 (NH), 1685(C=O), 1630(C=N)
i.
1
HNMR(DMSO-‐d
6
) Spectral data(δ inppm)
VII
a: 2.22 (s, 3H CH
3
), 2.40 (s, 3H, CH
3
), 2.46 (s, 3H, COCH
3
), 5.26 (s, 2H, OCH
2
), 6.8 (s, H,
Ar-‐NH), 7.1-‐7.3 (m, 9H, Ar-‐H), 7.4(d, 2H, C
6
H
4
), 7.7(d, 2H,C
6
H
4
).
VII
g: 2.20 (s, 3HCH
3
), 2.26 (s, 3H, CH
3
), 2.39 (s, 3H, CH
3
), 2.44 (s, 3H, COCH
3
), 5.24 (s, 2H,
OCH
2
), 6.8(s, H, Ar -‐NH), 7.1-‐7.3(m, 9H, Ar-‐H), 7.4 (d, 2H, C
6
H
4
), 7. 7(d, 2H, C
6
H
4
).
VII
h: 2.19 (s, 3H, CH
3
), 2.37 (s, 3H, COCH
3
), 2.24 (s, 2H, CH
3
), 4.92 (s, 2H, OCH
2
), 6.8 (s, H,
Ar-‐NH), 7.1-‐7.3 (m, 9H, Ar-‐H), 7.4 (d, 2H, C
6
H
4
), 7.7(d, 2H, C
6
H
4
).
VII
i: 2.18 (s, 3HCH
3
), 2.39 (s, 3H, CH
3
), 2.43 (s, 3H, COCH
3
), 3.89 (s, 3H, OCH
3
), 5.24 (s, 2H,
OCH
2
), 6.8(s, H, Ar-‐NH), 7.1-‐7.3 (m, 9H, Ar-‐H), 7.4 (d, 2H, C
6
H
4
), 7.7(d, 2H, C
6
H
4
).
VII
j: 2.16 (s, 3HCH
3
), 2.35 (s, 3H, CH
3
), 2.40 (s, 3H, COCH
3
), 5.22 (s, 2H, OCH
2
), 6.8 (s, H, Ar
-‐NH), 7.1-‐7.3 (m, 9H, Ar-‐H), 7.4 (d, 2H, C
6
H
4
), 7.7(d, 2H, C
6
H
4
).
j. Elemental analysis data of compounds VIII (M.P., Yield, Molecular formula, Element:
Found%, (Calc%)
VIII
: 150
o
C, 65 %, C
19
H
20
N
6
O
3
S, C:55.33(55.19), H:4.85(4.68), N:20.38(20.21),
O:16.50(16.35), S:7.76(7.62).
k. IR(KBr) Spectral data(ν
max
incm
-‐1
)
VIII
: 3126 (oxadiazoleNH), 3180 (NH), 1603 (C=N), 1670(C=O), 1134(C=S).
l.
1
HNMR(DMSO-‐d
6
) Spectral data(δ inppm)
VIII
: 2.3 (s, 3HCH
3
), 5.45 (s, 2H, OCH
2-‐
), 6.8 (s, H, Ar -‐ NH), 7.1–7.3 (m, 5H, Ar -‐ H),7.4 (d,
2H, C
6
H
4
), 7.7(d, 2H, C
6
H
4
), 14.7(s, H, thiol-‐thione tautomericprotonNH)
m. Elemental analysis data of compounds IX (R
1
=H, R
2
, M.W., M.P., Yield, Molecular
formula, Element: Found%, (Calc%)
IX
a:
p
-‐tolyl, 240
o
C, 75 %, C
27
H
25
N
7
O
3
S, C:61.48(61.32), H:4.47(4.30), N:18.59(18.45),
O:9.10(8.93), S:6.07(5.90).
IX
b:
p
-‐anisyl, 245
o
C, 77 %, C
27
H
25
N
7
O
4
S, C:59.66(59.48), H:4.60(4.56), N:18.04(17.85),
O:11.78(11.62), S:5.89(5.69).
IX
c:
p
-‐flurophenyl,
235
o
C,
78 %,
C
26
H
22
N
7
O
3
SFl,
C:58.76(58.65),
H:4.14(3.98),
N:18.45(18.33), O:9.04(8.86), S:6.02(5.80), Fl:3.55 (3.38).
IX
d:
p
-‐chlorophenyl, 250
o
C, 73 %, C
26
H
22
N
7
O
3
SCl, C:56.98(56.75), H:4.01(3.83),
N:17.88(17.69), O:8.76(8.61), S:5.84(5.69), Cl:6.48(6.31).
IX
e:
p
-‐bromophenyl, 230
o
C, 80 %, C
26
H
23
N
7
O
3
Br, C:52.71(52.58), H:3.71(3.59),
N:16.55(16.38), O:8.10(7.92), S:5.40(5.23), Br:13.49(13.30).
IX
f:
p
-‐nitrophenyl, 255
o
C, 83%, C
26
H
22
N
8
O
5
S, C:55.91(55.74), H:3.94(3.78), N:20.07(19.87),
O:14.33(14.21), S:5.73(5.57).
IX
g: diethyl, 260
o
C, 72 %, C
28
H
37
N
8
O
3
S, C:59.46(59.28), H:6.54(6.39), N:19.82(19.70),
O:8.49(8.32), S:5.66(5.44).
IX
h: diphenyl, 266
o
C, 70 %, C
32
H
27
N
7
O
3
S, C:65.29(65.18), H:4.52(4.62), N:17.01(16.63),
O:8.03(8.14), S:5.27(5.44).
IX
i: morpholinyl, 270
o
C, 70%, C
20
H
18
N
7
O
4
S, C:53.09(52.89), H:3.98(3.76), N:21.68(21.52),
O:14.15(13.98), S:7.07(6.84).
IX
j: piperazinyl, 272
o
C, 72%, C
22
H
20
N
7
O
3
S, C:57.14(56.98), H:4.32(4.17), N:21.21(21.07),
O:10.38(10.23), S:6.92(6.76).
