Novel compounds containing1,3,4-‐oxadiazole…
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3. RESULTSANDDISCUSSION
3.1. Characterizationof synthesizedcompounds
a. Elemental analysis details of compounds V (-‐R, M.P., Yield, Molecular formula,
Element: Found%, (Calc%))
V
a: H, 152
o
C, 65 %, C
18
H
22
N
6
O
3,
C:58.37(58.25), H:5.94(5.86), N:22.70(22.65),
O:12.97(12.85).
V
b: CH
3
, 153
o
C, 60 %, C
19
H
24
N
6
O
3,
C:59.37(59.26), H:6.25 (6.17), N:21.87(21.76),
O:12.23(12.14).
V
c: OCH
3
, 156
o
C, 75%, C
19
H
24
N
6
O
3,
C:57.00(55.85), H:6.00 (5.68), N:21.00 (19.85), O:16.00
(15.85).
V
d: OC
2
H
5
, 168
o
C, 80 %, C
20
H
26
N
6
O
4,
C:57.97(57.85), H:6.28(6.18), N:20.28(20.20),
O:15.45(15.35).
V
e: Cl, 174
o
C, 75 %, C
18
H
21
N
6
O
3
Cl, C:53.39(53.29), H:5.19(5.10), N:20.76(20.66),
O:11.86(11.76), Cl:8.77(8.66).
V
f: Br, 169
o
C, 65 %, C
18
H
21
N
6
O
3
Br, C:48.11(47.98), H:4.71(4.60), N:18.17(18.07),
O:10.89(10.78), Br:17.69(17.58).
b. IR(KBr) Spectral data(ν
max
incm
-‐1
)
V
a: 3445, 3425 (NH
2
), 3305(NH), 1665(C=O), 1620(C=N).
V
b: 3400, 3420(NH
2
), 3285(NH), 1665(C=O), 1610(C=N).
V
c: 3425, 3405 (NH
2
), 3200(NH), 1615(C=N), 1555(C=O).
V
d: 3435, 3415(NH
2
), 3300(NH), 1615(C=N), 1660(C=O).
V
e: 3420, 3400(NH
2
), 3275(NH), 1645(C=O), 1610(C=N).
V
f: 3444, 3424 (NH
2
), 3290(NH), 1650 (C=O), 1605(C=N).
c.
1
HNMR(DMSO–d
6
) Spectral data(δ inppm)
V
a: 1.2 (s, 3H, CH
3
), 2.1 (s, 2H, NH
2
), 3.85 (s, 2H, O-‐CH
2
-‐CO) 6.8 (s, 1H, Ar-‐NH) 7.1-‐7.3 (m,
5H, C
6
H
5
), 7.4(d, 2H, C
6
H
4
), 7.7(d, 2H,C
6
H
4
), 8.4(s,1H,NH)
V
b: 0.9 (s, 3H, CH
3
), 1.16 (s, 3H, CH
3
), 2.06 (s, 2H, NH
2
), 3.80(s, 2H, O-‐CH
2
-‐CO) 6.8(s,1H,Ar-‐
NH)7.1-‐7.3 (m, 4H, C
6
H
4
),7.4(d, 2H, C
6
H
4
), 7.7(d, 2H,C
6
H
4
), 8.36(s, 1H, N, CONH)
V
c: 1.12 (s, 3H, CH
3
), 2.02 (s, 2H, NH
2
), 3.24 (s, 3H, OCH
3
), 3.76 (s, 2H, O-‐CH
2
-‐CO), 6.8 (s,
1H, Ar–NH), 7.1-‐7.3(m, 4H, C
6
H
4
), 7.4(d, 2H, C
6
H
4
), 7.7(d, 2H, C
6
H
4
), 8.32(s, 1H, NH)
V
d: 0.9 (s, 3H, CH
3
), 1.11 (t, 3H, CH
3
), 2.06 (s, 2H, NH
2
), 3.14 (q, 2H, O–CH
2
), 3.8 (s, 2H, O-‐
CH
2
-‐CO), 6.8 (s, H, Ar–NH), 7.1-‐7.3 (m, 4H, C
6
H
4
), 7.4 (d, 2H,C
6
H
4
), 7.7(d,2H,C
6
H
4
),
8.36
(s,1H,NH)
V
e: 1.08 (s, 3H, CH
3
), 2.08 (s, 2H, NH
2
), 3.82 (s, 2H, O-‐CH
2
-‐CO) 6.8 (s, 1H, Ar–NH), 7.1-‐7.3
(m, 4H, C
6
H
4
), 7.4(d, 2H, C
6
H
4
), 7.7(d, 2H, C
6
H
4
), 8.38(s, 1H, NH)
V
f: 1.04 (s, 3H, CH
3
), 2.04 (s, 2H, NH
2
), 3.78 (s, 2H, O-‐CH
2
-‐CO), 6.8 (s, 1HAr–NH), 7.1-‐7.3
(m, 4H, C
6
H
4
), 7.4(d, 2H, C
6
H
4
), 7.7(d, 2H, C
6
H
4
), 8.34(s, 1H, NH)
d. Elemental analysis details of compounds VI (-‐R, -‐R
1
, -‐R
2
, M.P., Yield, Molecular
formula)
VI
a: -‐H, -‐H, -‐C
6
H
5,
240
o
C, 75 %, C
26
H
28
N
6
O
3,
C:66.10(65.95), H:5.93(5.83), N:17.93(17.80),
O:10.16(10.02).
VI
b: -‐CH
3,
-‐CH
3,
-‐C
6
H
5,
245
o
C, 77 %, C
27
H
30
N
6
O
3,
C:66.66(66.50), H:6.17(6.05),
N:17.28(17.12), O:9.87(9.72).
VI
c: OCH
3,
CH
3,
C
6
H
5,
35
o
C, 72%, C
27
H
30
N
6
O
4,
C:64.54(64.42), H:5.97(5.83), N:16.73(16.58),
O:12.74(12.62).
VI
d: OC
2
H
5
, CH
3,
C
6
H
5,
250
o
C, 73 %, C
28
H
32
N
6
O
4,
C:65.11(64.95), H:6.20(6.05),
N:16.27(16.12), O:12.40(12.22).
VI
e: Cl, CH
3,
C
6
H
5,
230
o
C, 75, C
26
H
27
N
6
O
3
Cl, C:61.59(61.42), H:5.33(5.23), N:16.58(16.46),
O:9.47(9.33), Cl:7.00(6.86).
VI
f: Br, CH
3,
C
6
H
5,
255
o
C, 78 %, C
27
H
27
N
6
O
3
Br, C:56.63(56.52), H:4.90(4.78),
N:15.24(15.07), O:8.71(8.58), Br:14.50(14.37).
