Page 215 - 80_01

Novel
compounds
containing
1,3,4-­-oxadiazole…

h.
IR
(KBr)
Spectral
data
(?max
in
cm-­-1)

VIIa:
3206
(NH),
1685
(C=O),
1620
(C=N)

VIIb:
3195
(NH),
1690
(C=O),
1622
(C=N)

VIIc:
3230
(NH),
1685
(C=O),1625
(C=N)

VIId:
3215
(NH),
1695
(C=O),
1624
(C=N)

VIIe:
3230
(NH),
1675
(C=O),
1630
(C=N)

VIIf:
3210
(NH),
1685
(C=O),
1627
(C=N)

VIIg:
3180
(NH),
1695
(C=O),
1627
(C=N)

VIIh:
3195
(NH),
1700
(C=O),
1629
(C=N)

VIIi:
3245
(NH),
1705
(C=O),
1630
(C=N)

VIIj:
3240
(NH),
1685
(C=O),
1630
(C=N)

i.
1H
NMR
(DMSO-­-d6)
Spectral
data
(d
in
ppm)

VIIa:
2.22
(s,
3H
CH3),
2.40
(s,
3H,
CH3),
2.46
(s,
3H,
COCH3),
5.26
(s,
2H,
OCH2),
6.8
(s,
H,

Ar-­-NH),
7.1-­-7.3
(m,
9H,
Ar-­-H),
7.4(d,
2H,
C6H4),
7.7
(d,
2H,C6H4).

VIIg:
2.20
(s,
3H
CH3),
2.26
(s,
3H,
CH3),
2.39
(s,
3H,
CH3),
2.44
(s,
3H,
COCH3),
5.24
(s,
2H,

OCH2),
6.8
(s,
H,
Ar
-­-
NH),
7.1-­-7.3
(m,
9H,
Ar-­-H),
7.4
(d,
2H,
C6H4),
7.
7
(d,
2H,
C6H4).

VIIh:
2.19
(s,
3H,
CH3),
2.37
(s,
3H,
COCH3),
2.24
(s,
2H,
CH3),
4.92
(s,
2H,
OCH2),
6.8
(s,
H,

Ar-­-NH),
7.1-­-7.3
(m,
9H,
Ar-­-H),
7.4
(d,
2H,
C6H4),
7.7
(d,
2H,
C6H4).

VIIi:
2.18
(s,
3H
CH3),
2.39
(s,
3
H,
CH3),
2.43
(s,
3H,
COCH3),
3.89
(s,
3H,
OCH3),
5.24
(s,
2H,

OCH2),
6.8
(s,
H,
Ar-­-NH),
7.1-­-7.3
(m,
9H,
Ar-­-H),
7.4
(d,
2H,
C6H4),
7.7
(d,
2H,
C6H4).

VIIj:
2.16
(s,
3H
CH3),
2.35
(s,
3H,
CH3),
2.40
(s,
3H,
COCH3),
5.22
(s,
2H,
OCH2),
6.8
(s,
H,
Ar

-­-
NH),
7.1-­-7.3
(m,
9H,
Ar-­-H),
7.4
(d,
2H,
C6H4),
7.7
(d,
2H,
C6H4).

j.
Elemental
analysis
data
of
compounds
VIII
(M.P.,
Yield,
Molecular
formula,
Element:

Found
%,
(Calc
%
)

VIII:
150
oC,
65
%,
C19H20N6O3S,
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
(?max
in
cm-­-1)

VIII:
3126
(oxadiazole
NH),
3180
(NH),
1603
(C=N),
1670
(C=O),
1134
(C=S).

l.
1H
NMR
(DMSO-­-d6)
Spectral
data
(d
in
ppm)

VIII:
2.3
(s,
3H
CH3),
5.45
(s,
2H,
OCH2-­-),
6.8
(s,
H,
Ar
-­-
NH),
7.1–7.3
(m,
5H,
Ar
-­-
H),7.4
(d,

2H,
C6H4),
7.7
(d,
2H,
C6H4),
14.7
(s,
H,
thiol-­-thione
tautomeric
proton
NH)

m.
Elemental
analysis
data
of
compounds
IX
(R1=H,
R2,
M.W.,
M.P.,
Yield,
Molecular

formula,
Element:
Found
%,
(Calc
%
)

IXa:
p-­-tolyl,
240oC,
75
%,
C27H25N7O3S,
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).

IXb:
p-­-anisyl,
245oC,
77
%,
C27H25N7O4S,
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).

IXc:
p-­-flurophenyl,
235oC,
78
%,
C26H22N7O3SFl,
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).

IXd:
p-­-chlorophenyl,
250oC,
73
%,
C26H22N7O3SCl,
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).

IXe:
p-­-bromophenyl,
230oC,
80
%,
C26H23N7O3Br,
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).

IXf:
p-­-nitrophenyl,
255oC,
83
%,
C26H22N8O5S,
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).

IXg:
diethyl,
260oC,
72
%,
C28H37N8O3S,
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).

IXh:
diphenyl,
266
oC,
70
%,
C32H27N7O3S,
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).

IXi:
morpholinyl,
270oC,
70
%,
C20H18N7O4S,
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).

IXj:
piperazinyl,
272oC,
72
%,
C22H20N7O3S,
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).

209