TABLE 2. Characteristics of Compounds 3a-l*
Found, %
Com-
Empirical
formula
——————
Yield,
%
Calculated, %
mp, °С
Rf
1Н NMR spectrum, δ, ppm (J, Hz)
pound
C
H
N
3
3
а*2
С12H16N4O
61.92
6.71
6.94
24.13
24.12
289-290
242-244
0.59
0.64
1.24 (6Н, s, 2СН3); 2.41 (3Н, s, СН3); 3.36 (2Н, s, 9-СН2); 4.77 (2Н, s, СН2О);
5.12 (2Н, s, NH2); 11.23 (1Н, s, NH)
92.4
93.9
6
2.05
b
C14H20N4O
64.31
7.63
21.41
1.10 (3Н, t, J = 7.5, СН2–СН3); 1.25 (6Н, 2СН3);
6
4.59
7.74
21.52
1
3
.75 (2Н, m, J = 7.5, СН2–СН3); 2.6 (2Н, t, J = 7.5, СН2–С2Н5);
.05 (2Н, s, 9-СН2); 4.65 (2Н, s, СН2О); 4.90 (2Н, s, NH2); 11.60 (1H, s, NH)
3
3
c
C14H20N4O
C18H20N4O
64.46
4.59
7.51
7.74
21.44
21.52
256-257
232-233
0.68
0.76
1.30 (6H, s, 2CH3); 1.41 (6H, d, J = 7, СН(СН3)2); 2.88 (1Н, m, J = 7, СН);
84.6
75.9
6
3
.33 (2Н, s, 9-СН2); 4.92 (2Н, s, СН2О); 5.63 (2Н, s, NH2); 11.37 (1H, s, NH)
d
69.89
6.46
18.02
1.23 (6Н, s, 2СН3); 3.05 (2Н, s, 9-СН2); 4.00 (2Н, s, СН2С6Н5);
7
0.11
6.54
18.17
4
1
.65 (2Н, s, СН2О); 5.01 (2Н, s, NH2); 7.05-7.30 (5H, m, С6Н5);
1.80 (1Н, s, NH)
3
e
C15H22N4O
65.51
5.67
8.14
8.08
20.29
20.42
241-242
0.61
0.95 (6Н, d, J = 6, СН(СН3)2); 1.22 (6Н, s, 2СН3); 2.15 (1Н, m, J = 6, СН);
73.8
6
2
4
.50 (2Н, d, J = 8, СН–СН2); 3.05 (2Н, s, 9-СН2); 4.71 (2Н, s, СН2О);
.95 (2Н, s, NH2); 11.70 (1H, s, NH)
3
3
f
C13H18N4S
C15H22N4S
59.37
9.51
6.78
6.91
21.22
21.35
257-258
253-254
0.72
0.59
1.21 (3H, t, J = 7, СН2СН3); 1.30 (6Н, s, 2СН3); 2.82 (2Н, q, J = 7.5, СН2СН3);
85.1
65.1
5
3
.55 (2Н, s, 9-СН2); 3.95 (2Н, s, СН2S); 5.65 (2H, s, NH2); 11.4 (1H, s, NH)
g
61.94
7.54
19.11
0.86 (3H, t, J = 7, СН2СН3); 1.35 (6Н, s, 2СН3); 1.38-2.05 (4Н, m, 2СН2);
6
2.03
7.63
19.29
2
5
.86 (2Н, t, J = 7, СН2С3Н7); 3.57 (2Н, s, 9-СН2); 3.93 (2Н, s, СН2S);
.62 (2H, s, NH2); 11.2 (1H, s, NH)
3
3
h
i
C14H20N4S
60.75
0.84
7.14
7.29
20.09
20.27
268-269
236-237
0.74
0.69
1.28 (6H, t, J = 7, СН(СН3)2); 1.40 (6Н, s, 2СН3); 3.25 (2Н, s, 9-СН2);
89.2
92.1
6
3
.35 (1Н, m, J = 7, СН); 3.85 (2Н, s, СН2S); 4.80 (2H, s, NH2); 11.6 (1H, s, NH)
C15H16N4ОS
59.77
5.26
18.48
1.30 (6H, s, 2CH3); 3.55 (2H, s, 9-CH2); 4.25 (2H, s, CH2S); 5.65 (2H, s, NH2);
5
9.98
5.37
18.65
6
1
.49 (1H, t, J = 3.4, СН); 7.10 (1Н, d, J = 3.4, СН); 7.65 (1Н, d, J = 3.4);
1.20 (1Н, s, СН)
3
3
j
C17H18N4S
C12H16N4
65.69
5.78
5.73
5.84
17.94
18.05
213-214
240-241
0.63
0.71
1.35 (6Н, s, 2СН3); 3.40 (2Н, s, 9-СН2); 3.78 (2Н, s, СН2S); 5.10 (2H, s, NH2);
87.0
93.4
6
7
.45-7.52 (5H, m, С6Н5); 11.33 (1Н, s, NH)
k
66.57
7.37
25.71
1.25 (3H, t, J = 7, СН2СН3); 1.76-1.85 (4Н, m, 2СН2);
6
6.64
7.46
25.90
2
4
.60-2.80 (4Н, m, 6-СН2, СН2СН3); 3.14 (2Н, t, J = 6.6, 9-СН2);
.60 (2Н, s, NH2); 11.50 (1H, s, NH)
3
l
C16H16N4
72.51
2.70
6.03
6.10
21.04
21.20
240-242
0.62
1.60-1.95 (4H, m, 2СН2); 2.65 (2Н, J = 6.6, 6-СН2); 3.25 (2Н, t, J = 6.6, 9-СН2); 83.7
7
4
.40 (2Н, s, NH2); 7.35-7.42 (5H, m, С6Н5); 11.42 (1Н, s, NH)
_
*
*
______
IR spectrum of compounds 3a-l (thin film), ν, cm : 3160-3420 (NH, NH
-1
2
), 1610-1630 (NH bend), 1580-1600 (C=C arom.).
Mass spectrum, m/z (Irel, %): [M] 232 (91), 217 (19), 203 (17), 174 (100), 160 (24).
2
+