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G. Ortar et al. / European Journal of Medicinal Chemistry 43 (2008) 62e72
Table 3
Elemental analysis data
Compound
Molecular formula
Calculated C, H, N
Found C, H, N
1
C
17H17N5O
17H17N5O
C, 66.43; H, 5.58; N, 22.79
C, 66.43; H, 5.58; N, 22.79
C, 58.76; H, 6.16; N, 28.55
C, 60.21; H, 6.61; N, 27.01
C, 58.76; H, 6.16; N, 28.55
C, 60.21; H, 6.61; N, 27.01
C, 32.67; H, 2.74; N, 28.57
C, 32.67; H, 2.74; N, 28.57
C, 61.70; H, 5.18; N, 23.99
C, 60.32; H, 7.31; N, 23.45
C, 61.27; H, 7.58; N, 22.56
C, 61.70; H, 5.18; N, 23.99
C, 61.70; H, 5.18; N, 23.99
C, 60.32; H, 7.31; N, 23.45
C, 61.27; H, 7.58; N, 22.56
C, 71.17; H, 5.12; N, 23.71
C, 62.05; H, 5.79; N, 32.16
C, 63.81; H, 6.43; N, 29.77
C, 33.05; H, 1.85; N, 21.41
C, 29.21; H, 1.91; N, 30.28
C, 76.25; H, 5.12; N, 11.86
C, 76.25; H, 5.12; N, 11.86
C, 76.78; H, 5.64; N, 11.19
C, 73.74; H, 8.25; N, 11.47
C, 70.04; H, 8.08; N, 10.21
C, 64.51; H, 4.69; N, 25.07
C, 64.51; H, 4.69; N, 25.07
C, 65.52; H, 5.15; N, 23.88
C, 62.70; H, 7.37; N, 24.37
C, 63.76; H, 7.69; N, 23.24
C, 66.49; H, 5.49; N, 22.65
C, 66.37; H, 5.62; N, 22.87
C, 58.59; H, 6.31; N, 28.67
C, 60.37; H, 6.44; N, 26.83
C, 59.02; H, 6.03; N, 28.18
C, 60.40; H, 6.47; N, 27.33
C, 32.72; H, 2.72; N, 28.57
C, 32.59; H, 2.70; N, 28.49
C, 61.48; H, 5.09; N, 24.08
C, 60.14; H, 7.28; N, 23.47
C, 61.03; H, 7.49; N, 22.48
C, 61.54; H, 5.07; N, 24.16
C, 61.67; H, 5.19; N, 23.90
C, 59.97; H, 7.44; N, 23.22
C, 61.30; H, 7.67; N, 22.67
C, 71.39; H, 5.18; N, 23.64
C, 62.16; H, 5.65; N, 32.47
C, 63.58; H, 6.19; N, 29.75
C, 32.89; H, 1.97; N, 21.37
C, 29.36; H, 1.87; N, 30.35
C, 76.47; H, 5.07; N, 11.68
C, 76.32; H, 5.02; N, 12.01
C, 76.68; H, 5.60; N, 11.13
C, 73.56; H, 8.32; N, 11.53
C, 69.78; H, 7.99; N, 10.34
C, 64.47; H, 4.39; N, 25.40
C, 64.39; H, 4.51; N, 24.93
C, 65.72; H, 5.07; N, 23.80
C, 62.76; H, 7.45; N, 24.12
C, 63.46; H, 7.58; N, 23.24
2
C
3
C12H15N5O
C13H17N5O
4
5
C
12H15N5O
13H17N5O
6
C
7
C12H12IN9O2
C12H12IN9O2
8
9
C
18H18N6O2
18H26N6O2
12
13
14
15
17
18
22
23
24
29
30
36
37
38
39
40
41
42
43
44
45
C
C19H28N6O2
C18H18N6O2
C
18H18N6O2
18H26N6O2
C
C19H28N6O2
C14H12N4
C9H10N4
C10H12N4
C9H6IN5O
C9H7IN8O
C15H12N2O
C
15H12N2O
C16H14N2O
15H20N2O
C
C16H22N2O
C15H13N5O
C15H13N5O
C16H15N5O
C15H21N5O
C16H23N5O
6.1.3. 5-Phenethyl-1H-tetrazole (23)
13C NMR (75 MHz) d 25.65, 33.61, 37.58, 39.12, 126.68,
128.58, 139.24, 147.84, 156.37. Anal. (C12H15N5O) C, H, N.
The title compound was prepared from 3-phenylpropaneni-
trile (20) following the same procedure that was used for the
synthesis of 22. Yield 70%; mp 80e85 ꢁC; IR 3134, 3029,
2859, 2730, 2626, 1560, 1497, 1454, 1258, 1108,
6.1.5. 5-(3-Phenylpropyl)-1H-tetrazole (24)
The title compound was prepared from 4-phenylbutyroni-
trile (21) following the same procedure that was used for the
synthesis of 22. Yield 55%; mp 80e85 ꢁC; IR 3130, 3024,
2864, 2730, 2622, 1568, 1495, 1450, 1421, 1256, 1107,
1
1050 cmꢃ1; H NMR (300 MHz) d 3.15 (2H, t, J ¼ 7.6 Hz),
3.38 (2H, t, J ¼ 7.6 Hz), 7.13e7.25 (5H, m); 13C NMR
(75 MHz) d 25.29, 33.67, 126.72, 128.30, 128.67, 139.10,
156.11. Anal. (C9H10N4) C, H, N.
1
1047 cmꢃ1; H NMR (300 MHz) d 2.19 (2H, m), 2.71 (2H,
t, J ¼ 7.5 Hz), 3.08 (2H, t, J ¼ 7.7 Hz), 7.11e7.27 (5H, m);
13C NMR (75 MHz) d 22.91, 29.03, 34.99, 126.25, 128.42,
128.52, 140.54, 156.77. Anal. (C10H12N4) C, H, N.
6.1.4. N,N-Dimethyl-5-phenethyl-1H-tetrazole-1-
carboxamide (3) and N,N-dimethyl-5-phenethyl-2H-
tetrazole-2-carboxamide (5)
The title compounds were prepared from 23 following the
same procedure that was used for the synthesis of 1, 2 using
hexane/AcOEt ¼ 1/1 as eluent for the chromatographic separa-
tion of regioisomers. Compound 5 (less polar, 23%): oil; IR
(CHCl3) 3009, 2941, 1740, 1498, 1393, 1311, 1252, 1168,
6.1.6. N,N-Dimethyl-5-(3-phenylpropyl)-1H-tetrazole-1-
carboxamide (4) and N,N-dimethyl-5-(3-phenylpropyl)-2H-
tetrazole-2-carboxamide (6)
The title compounds were prepared from 24 following the
same procedure that was used for the synthesis of 1, 2 using
preparative layer chromatography (silica gel, 0.5 cm thick)
and hexane/acetone ¼ 7/3 as eluent for the separation of
regioisomers. Compound 6 (less polar, 38%): oil; IR (CHCl3)
3024, 2942, 2864, 1740, 1603, 1497, 1453, 1393, 1310,
1
1130, 1070 cmꢃ1; H NMR (300 MHz) d 3.01 (3H, s), 3.22
(3H, s), 3.11e3.34 (4H, m), 7.14e7.32 (5H, m); 13C NMR
(75 MHz) d 27.12, 33.79, 38.05, 39.00, 126.39, 128.37,
128.52, 140.09, 147.92, 165.53. Anal. (C12H15N5O) C, H, N.
Compound 3 (more polar, 17%): oil; IR (CHCl3) 3014,
1
1167, 1071 cmꢃ1; H NMR (300 MHz) d 2.16 (2H, m), 2.70
1
2941, 1728, 1497, 1396, 1257, 1236, 1088, 1076 cmꢃ1; H
(2H, t, J ¼ 7.5 Hz), 2.99 (2H, t, J ¼ 7.6 Hz) 3.09 (3H, s),
3.24 (3H, s), 7.14e7.33 (5H, m); 13C NMR (75 MHz)
d 24.76, 29.26, 35.11, 38.06, 39.10, 126.03, 128.42, 128.49,
NMR (300 MHz) d 2.76 (3H, s), 3.09 (3H, s), 3.13 (2H, t,
J ¼ 7.6 Hz), 3.48 (2H, t, J ¼ 7.6 Hz), 7.13e7.31 (5H, m);