M. Pietrzak, A. Bajorek / Dyes and Pigments 96 (2013) 63e70
67
Table 2
Structures, and characteristics of the tested dyes.
Ab. Structure
Yield Melting point [ꢂC], 1H and 13C NMR (DMSO-d6) [cmꢀ1
d [ppm], IR (KBr) n ]
%
H
N
H
3a
56
M.p.: 255e258; 1H NMR: 6.90 (d, J ¼ 8.4 Hz, 2H), 6.61 (d, J ¼ 8.4 Hz, 2H), 6.28 (s, 2H, NH2), 5.37 (s, 2H, NH2), 2.81 (t, J ¼ 6 Hz, 2H), 2.23
(t, J ¼ 5.8 Hz, 2H), 1.69 (m, 2H), 1.55 (m, 2H); 13C NMR: 150.9 (C), 150.6 (C), 148.9 (C), 146.1 (C), 129.1 (CH), 124.6 (C), 123.7 (C), 116.1
(C), 115.5 (C), 113.3 (CH), 95.8 (C), 94.7 (C), 29.0 (CH2), 27.0 (CH2), 22.1 (CH2), 21.5 (CH2); IR (KBr): 2211, 1643, 1521, 1272, 823, 517
CN
NH
NC
2
H C
3
3b
3c
3d
37
58
52
M.p.: 252e254; 1H NMR: 7.08 (d, J ¼ 8.8 Hz, 2H), 6.78 (d, J ¼ 8.4 Hz, 2H), 6.29 (s, 2H, NH2), 2.96 (s, 6H, N(CH3)2), 2.82 (t, J ¼ 6.2 Hz, 2H),
2.23 (t, J ¼ 6.0 Hz, 2H), 1.70 (m, 2H), 1.55 (m, 2H); 13C NMR: 150.6 (C), 150.5 (C), 149.9 (C), 146.2 (C), 129.1 (CH), 124.6 (C), 124.0 (C),
116.1 (C), 115.5 (C), 111.6 (CH), 95.8 (C), 94.8 (C), 39.8 (NCH3) 29.0 (CH2), 27.0 (CH2), 22.1 (CH2), 21.5 (CH2); IR (KBr): 2217, 1633,
1528, 1366, 810
N
CN
NH
H C
3
NC
2
H C
5
2
2
M.p.: 178e180; 1H NMR: 7.03 (d, J ¼ 8.8 Hz, 2H), 6.69 (d, J ¼ 9.0 Hz, 2H), 6.26 (s, 2H, NH2), 3.36 (q, J ¼ 7.4 Hz, 4H, NCH2), 2.80 (t,
J ¼ 6 Hz, 2H), 2.23 (t, J ¼ 6 Hz, 2H), 1.69 (m, 2H), 1.54 (m, 2H), 1.10 (t, J ¼ 6.8 Hz, 6H, CH3); 13C NMR: 150.7 (C), 150.6 (C), 147.2 (C),
146.2 (C), 129.5 (CH), 124.7 (C), 122.8 (C), 116.2 (C), 115.5 (C), 110.5 (CH), 95.7 (C), 94.7 (C), 43.5 (NCH2), 29.0 (CH2), 27.1 (CH2), 22.1
(CH2), 21.5 (CH2), 12.5 (CH3); IR (KBr): 2223, 1637, 1524, 1353, 813
N
CN
NH
H C
5
NC
2
CH
3
H C
3
M.p.: 225e227; 1H NMR: 6.81 (d, J ¼ 8.2 Hz, 1H), 6.65e6.58 (m, 2H), 6.31 (s, 2H, NH2), 2.92 (s, 6H, N(CH3)2), 2.81 (t, J ¼ 5.9 Hz, 2H),
2.06 (m, 2H), 1.92 (s, 3H, ArCH3), 1.67 (m, 2H), 1.55 (m, 2H); 13C NMR: 150.7 (C), 150.6 (C), 150.2 (C), 146.5 (C), 134.8 (C) 128.4 (CH),
125.3 (C), 124.6 (C), 115.7 (C), 115.5 (C), 113.5 (CH), 110.0 (CH), 96.4 (C), 95.2 (C), 39.9 (N(CH3)2), 28.9 (CH2), 26.4 (CH2), 21.9 (CH2),
21.5 (CH2), 19.5 (ArCH3); IR (KBr): 2216, 1632, 1447, 798.
N
CN
H C
3
NC
NH
2
3e
3f
0
42
56
Compound could not be obtained
H C
3
H C
3
M.p.: 190e192; 1H NMR: 7.08 (d, J ¼ 8.8 Hz, 1H), 7.02 (s, 1H), 7.00 (d, J ¼ 7.2 Hz, 1H), 6.35 (s, 2H, NH2), 2.81 (t, J ¼ 5.8 Hz, 2H), 2.68 (s,
6H, N(CH3)2), 2.27 (s, 3H, ArCH3), 2.17 (m, 2H), 1.70 (m, 2H), 1.53 (m, 2H); 13C NMR: 152.3 (C), 150.6 (C), 150.1 (C), 146.4 (C), 130.9
(C), 130.7 (CH), 130.4 (C), 126.4 (CH), 124.4 (C), 117.9 (CH), 115.9 (C), 115.4 (C), 95.5 (C), 95.2 (C), 43.6 (N(CH3)2) 29.0 (CH2), 27.0
(CH2), 22.0 (CH2), 21.5 (CH2), 18.4 (ArCH3); IR (KBr): 2212, 1630, 1451, 1114, 820
N
H C
CN
3
NC
NH
2
H C CH
3
3
H C
3
3g
M.p.: 223e226; 1H NMR: 6.99 (d, J ¼ 8.2 Hz, 1H), 6.81 (d, J ¼ 8.0 Hz, 1H), 6.40 (s, 2H, NH2), 2.82 (t, J ¼ 5.8 Hz, 2H), 2.22 (s, 3H, ArCH3),
1.97 (m, 2H) 1.87 (s, 3H, ArCH3), 1.68 (m, 2H), 1.54 (m, 2H); 13C NMR: 152.3 (C), 150.7 (C), 150.5 (C), 146.5 (C), 134.0 (C), 131.1 (C),
130.4 (C), 125.3 (CH), 124.7 (C), 115.9 (CH), 115.5 (C), 115.4 (C), 95.8 (C), 95.3 (C), 44.1 (N(CH3)2) 28.9 (CH2), 26.3 (CH2), 21.8 (CH2),
21.5 (CH2), 16.7 (ArCH3), 14.6 (ArCH3); IR (KBr): 2222, 1644, 1452, 1282, 1042, 820
N
H C
CN
3
NC
NH
2
CH
3
H C
3
3h
3i
41
35
55
52
38
M.p.: 204e206; 1H NMR: 6.95 (s, 1H), 6.79 (s, 1H), 6.40 (s, 2H, NH2), 2.83 (t, J ¼ 5.6 Hz, 2H), 2.67 (s, 6H, N(CH3)2), 2.23 (s, 3H, ArCH3),
2.06 (m, 2H), 1.93 (s, 3H, ArCH3), 1.69 (m, 2H), 1.57 (m, 2H); 13C NMR: 152.1, 150.6, 150.0, 146.6, 132.2, 130.3, 130.1, 128.5, 124.6,
119.6, 115.5, 115.4, 95.7 (C), 95.3 (C), 43.6 (N(CH3)2), 28.9 (CH2), 26.4 (CH2), 21.9 (CH2), 21.5 (CH2), 18.8 (ArCH3), 17.9 (ArCH3); IR
(KBr): 2219, 1636, 1567, 1448, 1276, 888
N
CN
H C
3
NC
NH
H C
3
2
M.p.: 278e280; 1H NMR: 7.05 (d, J ¼ 8.6 Hz, 2H), 6.59 (d, J ¼ 8.6 Hz, 2H), 6.26 (s, 2H, NH2), 3.27 (t, J ¼ 6.2 Hz, 4H, N(CH2)2), 2.81 (t,
J ¼ 6.4 Hz, 2H), 2.23 (t, J ¼ 5.8 Hz, 2H), 1.97 (t, J ¼ 6.4 Hz, 4H), 1.70 (m, 2H), 1.55 (m, 2H); 13C NMR: 150.8 (C), 150.6 (C), 147.3 (C),
146.1 (C), 129.2 (CH), 124.7 (C), 123.0 (C), 116.1 (C), 115.5 (C), 111.1 (CH), 95.8 (C), 94.7 (C), 47.1 (N(CH2)2), 29.0 (CH2), 27.0 (CH2),
25.0 (CH2), 22.1 (CH2), 21.5 (CH2); IR (KBr): 2217, 1632, 1525, 1376, 810
N
CN
NC
NH
2
3j
M.p.: 254e256; 1H NMR: 7.09 (d, J ¼ 8.8 Hz, 2H), 6.99 (d, J ¼ 9.2 Hz, 2H), 6.33 (s, 2H, NH2), 3.22 (t, J ¼ 5.0 Hz, 4H, N(CH2)2), 2.82 (t,
J ¼ 6.2 Hz, 2H), 2.21 (t, J ¼ 5.4 Hz, 2H), 1.71e1.58 (m, 10H); 13C NMR: 151.0 (C), 150.6 (C), 150.3 (C), 146.3 (C), 129.1 (CH), 126.0 (C),
124.6 (C), 116.0 (C), 115.5 (C), 114.7 (CH), 95.7 (C), 95.0 (C), 48.7 (N(CH2)2), 29.0 (CH2), 27.0 (CH2), 25.2 (CH2), 23.9 (CH2), 22.1 (CH2),
21.4 (CH2); IR (KBr): 2217, 1631, 1518, 1238, 814
N
CN
NH
NC
NC
NC
2
3k
3l
M.p.: 236e238; 1H NMR: 6.91 (s, 1H), 6.89 (d, J ¼ 8.8 Hz, 1H), 6.56 (d, J ¼ 8.2 Hz, 1H), 6.29 (s, 2H, NH2), 3.32 (t, J ¼ 8.2 Hz, 2H, NCH2),
2.96e2.78 (m, 4H), 2.76 (s, 3H, NCH3), 2.22 (m, 2H), 1.70 (m, 2H), 1.54 (m, 2H); 13C NMR: 153.2, 150.9, 150.6, 146.1, 129.8, 127.7,
125.5, 124.7, 124.0, 116.1, 115.5, 106.2, 95.8, 94.8, 55.2 (NCH2), 35.3 (NCH3), 29.0 (CH2), 27.9 (CH2), 27.0 (CH2), 22.1 (CH2), 21.5 (CH2);
IR (KBr): 2218, 1633, 1563, 1274, 809
N
CN
H C
3
NH
2
M.p.: 257e260; 1H NMR: 6.88 (d, J ¼ 8.4 Hz, 1H), 6.79 (s, 1H), 6.61 (d, J ¼ 8.4 Hz, 1H), 6.27 (s, 2H, NH2), 3.25 (t, J ¼ 5.4 Hz, 2H, NCH2),
2.88 (s, 3H, NCH3), 2.81 (t, J ¼ 6.0 Hz, 2H), 2.71 (t, J ¼ 6.2 Hz, 2H), 2.23 (m, 2H), 1.90 (m, 2H), 1.70 (m, 2H), 1.55 (m, 2H); 13C NMR:
150.6 (C), 150.6 (C) 146.3 (C), 146.1 (C), 128.3 (CH), 127.1 (CH), 124.7 (C), 123.7 (C), 121.6 (C), 116.2 (C), 115.3 (C), 110.1 (CH), 95.7 (C),
N
CN
H C
3
NH
2
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