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I. Caleta et al. / IL FARMACO 59 (2004) 297–305
302
Table 5
Spectroscopic data of the compounds (5-17)
Com.
5*
IR (KBr)/ (cm-1)
1600, 1650 (C=N)
1H-NMR (DMSO-d6, TMS), d (ppm)
9.65 (s, 1H, amidino-NH,), 9.49 (s, 1H, amidino-NH), 9.23 (s, 1H, 169.8(s), 161.3(s), 147.7(s), 127.3(s), 127.1(s),
amidino-NH), 8.25 (s, 1H, H7), 7.71 (d, 1H, J=8.4 Hz, H5), 7.61 (d, 123.35(s), 122.97(s), 115.1(s), 45.15(s), 21.35(s)
1H, J=8.4 Hz, H4), 5.34 (s, 3H, amino-NH3+), 4.18-4.07 (m, 1H, -CH),
13C-NMR (DMSO-d6, TMS), d (ppm)
1.27 (d, 6H, J=6.3 Hz, -CH3)
6#
1615, 1675 (C=N)
1610(C=C)
11.50 (s, 1H, morpholino-NH+,), 9.90 (s, 1H, amidino-NH), 9.65 (s, 169.7(s), 162.75(s), 149.8(s), 127.9(s), 127.1(s),
1H, amidino-NH), 9.37 (s, 1H, amidino-NH), 8.55 (s, 2H, -NH2), 8.29 122.7(s), 122.1(s), 115.4(s), 63.0(s), 53.5(s),
(s, 1H, H7), 7.75 (d, 1H, J=8.4 Hz, H5), 7.5 (d, 1H, J=8.4 Hz, H4), 50.99(s), 37.05(s)
4.00-3.17 (m, 12H, -CH2-)
8*
8.49 (d, 1H, J=8.1 Hz, H7), 8.31 (d, 1H, J=8.1 Hz, H4), 8.26-8.193 (m, 171.8(s), 146.1(s), 142.6(s), 138.7(s), 133.4(s),
4H, -CH=CH-, H-arom.), 8.06 (d, 2H, J=8.4 Hz, H-arom.), 7.95-7.82 130.5(s), 130.2(s), 129.3(s), 128.8(s), 124.9(s),
(m, 2H, H5, H6), 4.41 (s, 3H, -CH3)
118.9(s), 117.8(s), 117.7(s), 113.98(s), 37.3(s)
9#
2210(C≡N),
1600(C=C)
8.64 (s, 1H, H7.), 8.04 (d, 1H, J=8.4 Hz, H4), 7.84 (d, 1H, J=8.4 Hz, 170.94(s), 155.83(s), 139.3(s), 134.83(s), 134.7(s),
H5), 7.75-7.72 (m, 3H, H-arom., -CH=CH-), 7.62 (d, 1H, J=16.2 Hz, 129.9(s), 129.7(s), 128.9(s), 127.95(s), 127.4(s)
-CH=CH-), 7.40-7.33 (m, 3H, H-arom.)
123.2(s), 121.1(s), 118.8(s), 107.25(s)
10#
2200(C≡N),
1600(C=C)
8.06 (d, 1H, J=7.8 Hz, H7), 7.94 (d, 1H, J=7.8 Hz, H4), 7.92 (d, 2H, 165.6(s), 153.3(s), 139.8(s), 135.2(s), 134.8(s),
J=8.4 Hz, H-arom.), 7.83 (d, 2H, J=8.4 Hz, H-arom.) 7.76 (d, 1H, 132.6(s), 128.2(s), 126.6(s), 125.7(s), 125.1(s),
J=16.2 Hz, -CH=CH-), 7.68 (d, 1H, J=16.2 Hz, -CH=CH-), 7.49-7.39 122.7(s), 122.2(s) 118.65(s), 109.5(s)
(m, 2H, H5, H6).
11*
12*
2205(C≡N),
1620(C=C)
8.70 (s, 1H, H7), 8.11 (d, 1H, J=8.7 Hz, H5), 7.96 (d, 1H, J=8.4 Hz, 170.7 (s), 156.25(s), 139.9 (s) 137.6(s), 135.5(s),
H4), 7.89-7.83 (m, 6H, H-arom., -CH=CH-)
133.2(s), 130.3(s), 129.1(s), 128.1(s), 124.95(s),
123.99(s), 119.2(s), 119.1(s), 112.2(s), 108.2(s),
1675(C=N),
1620(C=C)
9.78 (s, 1H, amidino-NH), 9.71 (s, 1H, amidino-NH), 9.35 (s, 1H, 170.2(s), 161.3(s), 156.0(s), 139.05(s), 134.9(s),
amidino-NH), 8.58 (s, 1H, H7), 8.14 (d, 1H, J=8.4 Hz, H4), 7.85-7.78 134.0(s), 129.7(s), 128.9(s), 127.9(s), 126.5(s),
(m, 4H, H-arom. and -CH=CH-), 7.70 (d, 1H, J=16.2 Hz, -CH=CH-), 125.8(s), 123.2(s), 122.2(s), 121.3(s), 45.15(s),
7.5-7.38 (m, 3H, H-arom.), 4.2-4.13 (m, 1H, -CH), 1.30 (6H, d, J=6.3 21.2(s)
Hz, -CH3)
13#
14#
15#
1670(C=N),
1618(C=C)
11.57 (s, 1H, morpholino-NH+), 10.18 (s, 1H, amidino-NH), 9.89 (s, 170.4(s), 163.0(s), 156.3(s), 139.2(s), 134.9(s),
1H, amidino-NH), 9.68 (s, 1H, amidino-NH), 8.68 (s, 1H, H7), 8.09 (d, 134.1(s), 129.95(s), 128.9(s), 127.97(s), 126.7 (s),
1H, J=8.4 Hz, H4), 7.92 (d, 1H, J=8.4 Hz, H5), 7.76-7.74 (m, 3H, 125.35(s), 123.5(s), 122.35(s), 121.35 (s), 63.1(s),
H-arom., -CH=CH-), 7.65 (d, 1H, J=16.2 Hz, -CH=CH-), 7.42-7.36 53.6(s), 51.1(s), 37.3(s)
(m, 3H, H-arom.), 3.95-3.78 (m, 6H, -CH2), 3.53-3.13 (m, 6H, -CH2)
1680(C=N),
1615(C=C)
9.60 (s, 1H, amidino-NH), 9.47 (s, 1H, amidino-NH), 9.18 (s, 1H, 165.7(s), 161.2(s), 153.4(s), 139.7(s), 135.5(s),
amidino-NH), 8.07 (d, 1H, J=7.8 Hz, H7), 7.95 (d, 3H, J=8.4 Hz, 134.2(s), 129.3(s), 128.9(s), 127.6(s), 126.6(s),
2H-arom., H4), 7.79 (d, 1H, J=16.2 Hz, -CH=CH-), 7.74 (d, 2H, J=8.4 125.7(s), 124.5(s), 122.7(s), 122.25(s), 45.1(s),
Hz, H-arom.), 7.71 (d, 1H, J=16.2 Hz, -CH=CH-), 7.49-7.39 (m, 2H, 21.2(s)
H5, H6), 4.08-4.03 (m, 1H, -CH), 1.22 (d, 6H, J=6.4 Hz, -CH3)
1675(C=N),
1610(C=C)
11.55 (s, 1H, morpholino-NH+), 10.09 (s, 1H, amidino-NH), 9.79 (s, 165.7(s), 162.7(s), 153.4(s), 140.0(s), 135.45(s),
1H, amidino-NH), 9.56 (s, 1H, amidino-NH), 8.07 (d, 1H, J=7.8 Hz, 134.2(s), 129.0 (s), 128.7(s), 127.65(s), 126.6(s),
H7), 8.98-7.88 (m, 5H, H-arom., H4), 7.79 (d, 1H, J=16.2 Hz, 125.7(s), 124.65(s), 122.7(s), 122.25(s), 63.1(s),
-CH=CH-), 7.70 (d, 1H, J=16.2 Hz, -CH=CH-), 7.49-7.39 (m, 2H, H5, 53.5(s), 51.1(s), 37.1(s)
H6), 3.94-3.80 (m, 6H, -CH2), 3.52-3.13 (m, 6H, -CH2)
16*
17*
1670(C=N),
1610(C=C)
9.8-9.2 (s, 6H, amidino-NH), 8.55 (s, 1H, H7), 8.10 (d, 1H, J=7.8 Hz, 169.6(s), 161.3 (s), 161.1(s), 155.9(s), 139.4(s),
H4), 7.97 (d, 2H, J=8.4 Hz, H-arom.), 7.84-7.77 (m, 5H, H-arom., H5, 137.1(s), 134.2(s), 129.6(s), 128.9(s), 127.8(s),
-CH=CH-), 4.14-4.07 (m, 2H, -CH), 1.24 (d, 6H, J=6.4 Hz, -CH3), 126.6(s), 126.1(s), 123.99(s), 123.4(s), 122.5(s),
1.23 (d, 6H, J=6.4 Hz, -CH3)
45.2(s), 45.1(s), 21.15(s), 21.2(s)
1675(C=N),
1615(C=C)
11.59 (s, 2H, morpholino-NH+), 10.26 (s, 1H, amidino-NH), 10.22 (s, 169.7(s), 162.8(s), 162.5(s), 156.1(s), 139.6(s),
1H, amidino-NH), 9.97 (s, 1H, amidino-NH), 9.92 (s, 1H, 137.2(s), 134.2(s), 129.1(s), 128.99(s), 127.9(s),
amidino-NH), 9.50 (s, 1H, amidino -NH), 9.69 (s, 1H, amidino-NH,), 126.8(s), 125.55(s), 124.1(s), 123.6(s), 122.5(s),
8.78 (s, 1H, H7), 8.19 (d, 1H, J= 8.4 Hz, H4), 8.07-7.92 (m, 7H, 63.0(s), 53.5(s), 51.0(s), 37.1(s)
H-arom., H5, -CH=CH-), 3.99-3.89 (m, 12H, -CH2-), 3.57-3.30 (m,
12H, -CH2-)
*At 300.13 MHz; #At 600.13 MHz
then the mixture was poured into 1 l of water. The solid was
collected and recrystallized from ethanol to yield 42.3% of
4-cyano-2-thiocyanatoaniline. The product (6.3 g,
0.036 mol), concentrated HCl (27 ml) and water (54 ml) were
refluxed for 2 h. The solution was cooled, and the product
was filtered off, washed with water, and recrystallized from
ethanol to yield 5.89 (39,7%) of 2-amino-6-
g
1
217-218°C). The H- and 13C-NMR spectra are in accor-
dance with literature data [24].