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1063
(2 ꢁ CH), 129.5 (C), 130.3 (CH), 130.5 (2 ꢁ CH), 138.1, 154.9, 158.9,
160.8 and 161.4 (5 ꢁ C).
2.2.1.8. 2-Amino-6-(4-hydroxyphenyl)-4-(3-methoxyphenyl)nicotino-
nitrile (4o). Colorless crystals; m.p = 215–218 °C; IR (KBr): 3352
and 3363 (NH2), 3335 (OH), 2225 (CN) cmꢀ1 1H NMR (400 MHz,
;
2.2.1.2. 2-Amino-4-(4-bromophenyl)-6-phenylnicotinonitrile (4i)
DMSO-d6) d = 3.82 (s, 3 H, OCH3), 6.83 (d, J = 8.4 Hz, 2 H, 2 ꢁ CH),
. Colorless crystals; m.p = 225–228 °C; IR (KBr): 3351 and 3359
6.90 (s, 2 H, NH2), 7.16 (s, 1 H, CH), 7.20 (d, J = 7.2 Hz, 2 H,
(NH2), 3340 (OH), 2227 (CN) cmꢀ1
;
1H NMR (400 MHz, DMSO-d6)
2 ꢁ CH), 7.44 (dd, J = 8.0 Hz, J = 7.2 Hz,
1 H, CH), 7.70 (d,
d = 6.98 (s, 2 H, NH2), 7.81 (s, 1 H, CH), 7.40–7.50 (m, 3 H,
3 ꢁ CH), 7.60 (d, J = 8.4 Hz, 2 H, 2 ꢁ CH), 7.69 (d, J = 8.4 Hz, 2 H,
2 ꢁ CH), 8.10 (d, J = 8.1 Hz, 2 H, 2 ꢁ CH); 13C NMR (100 MHz,
DMSO-d6) d = 87.9 (CN), 110.9 (CH), 116.9 (2 ꢁ CH), 124.4 (C),
127.3 (2 ꢁ CH), 128.8 (2 ꢁ CH), 129.7 (C), 130.4 (2 ꢁ CH), 132.2
(CH), 135.7, 137.7, 153.8, 160.1 and 160.3 (5 ꢁ C).
J = 8.0 Hz, 1 H, CH), 8.0 (d, J = 8.4 Hz, 2 H, 2 ꢁ CH), 9.93 (s, 1 H,
OH); 13C NMR (100 MHz, DMSO-d6) d = 55.4 (OCH3), 85.3 (CN),
109.5 and 114.6 (2 ꢁ CH), 115.9 (C) and 116.3 (2 ꢁ C), 117.8
(CH), 119.4 (C), 125.4 (CH), 127.5 and 128.9 (2 ꢁ C), 132.2 and
139.3 (2 ꢁ CH), 153.4 (CH), 158.2, 160.8, 161.7, 163.5 (4 ꢁ C).
2.2.1.9. 2-Amino-4-(3-bromophenyl)-6-(4-hydroxyphenyl)nicotino-
2.2.1.3. 2-Amino-6-phenyl-4,4’-bipyridine-3-carbonitrile (4j). Color-
less crystals; m.p = 215–218 °C; IR (KBr): 3356 and 3367 (NH2),
nitrile (4p). Colorless crystals; m.p = 226–229 °C; IR (KBr): 3354
and 3364 (NH2), 3342 (OH), 2220 (CN) cmꢀ1 1H NMR (400 MHz,
;
;
3344 (OH), 2221 (CN) cmꢀ1 1H NMR (400 MHz, DMSO-d6)
DMSO-d6) d = 6.83 (d, J = 8.0 Hz, 2 H, 2 ꢁ CH), 6.95 (s, 2 H, NH2),
7.20 (s, 1 H, CH), 7.50 (d, J = 7.2 Hz, 1 H, CH), 7.61 (dd, J = 7.2 Hz,
J = 6.8 Hz, 1 H, CH), 7.64 (d, J = 6.8 Hz, 1 H, CH), 7.84 (s, 1 H, CH),
8.02 (d, J = 8.0 Hz, 2 H, 2 ꢁ CH), 9.94 (s, 1 H, OH); 13C NMR
(100 MHz, DMSO-d6) d = 87.5 (CN), 107.8, 114.6, 115.5 and 115.9
(4 ꢁ CH), 116.5 (C), 118.2 (CH), 126.5 (2 ꢁ CH), 127.8 (C), 128.9,
132.8 and 135.8 (3 ꢁ CH), 154.3, 158.5, 160.8, 161.9 and 162.9
(5 ꢁ C).
d = 7.11 (s, 2 H, NH2), 7.15 (s, 1 H, CH), 7.3–7.6 (m, 5 H, 5 ꢁ CH),
7.63 (d, J = 5.6 Hz, 2 H, 2 ꢁ CH), 7.70 (d, J = 5.6 Hz, 2 H, 2 ꢁ CH);
13C NMR (100 MHz, DMSO-d6) d = 86.1(CN), 110.1 (CH), 113.6 (C),
123.3(2 ꢁ CH), 126.2 (C), 127.6 (2 ꢁ CH), 129.9 (2 ꢁ CH), 139.9
(2 ꢁ CH), 144.6 (CH), 149.8, 151.9, 156.4 and 162.6 (4 ꢁ C).
2.2.1.4. 2-Amino-6-(4-hydroxyphenyl)-4-(2-methoxyphenyl)nicotino-
nitrile (4k). Colorless crystals; m.p = 188–191 °C; IR (KBr): 3353
and 3360 (NH2), 3345 (OH), 2221 (CN) cmꢀ1 1H NMR (400 MHz,
;
2.2.1.10. 2-Amino-4-(3-chlorophenyl)-6-(4-hydroxyphenyl)nicotino-
DMSO-d6) d = 3.77 (s, 3 H, OCH3), 6.78 (d, J = 8.3 Hz, 2 H, 2 ꢁ CH),
6.99 (s, 2 H, NH2), 7.12 (s, 1 H,CH), 7.20–7.40 (m, 4 H, 4 ꢁ CH),
7.95 (d, J = 8.3 Hz, 2 H, 2 ꢁ CH), 9.90 (s, 1 H, OH); 13C NMR
(100 MHz, DMSO-d6) d = 54.3 (OCH3), 84.9 (CN), 108.2 (CH),
114.4 (CH), 115.5 (C), 115.3 (CH), 116.2 (C), 117.5 (CH), 118.8
(CH), 124.8 (CH), 127.4 (CH), 129.1 (C), 135.9 (CH), 137.9 (C),
153.1 (CH), 157.2, 160.8, 161.6 and 162.7 (4 ꢁ C).
nitrile (4q). Colorless crystals; m.p = 196–198 °C; IR (KBr): 3354
and 3361 (NH2), 3344 (OH), 2220 (CN) cmꢀ1 1H NMR (400 MHz,
;
DMSO-d6) d = 6.83 (d, J = 8.1 Hz, 2 H, 2 ꢁ CH), 6.96 (s, 2 H, NH2),
7.19 (s, 1 H, CH), 7.50–760 (m, 3 H, 3 ꢁ CH), 7.72 (s, 1 H, CH),
8.02 (d, J = 8.0 Hz, 2 H, 2 ꢁ CH), 9.95 (s, 1 H, OH); 13C NMR
(100 MHz, DMSO-d6) d = 87.3 (CN), 110.3, 114.2, 115.3 and 116.9
(4 ꢁ CH), 117.5 (C), 119.3 (CH), 123.7 and 127.3 (2 ꢁ CH), 128.9,
130.7 and 137.4 (3 ꢁ C), 154.4 (CH), 158.2, 160.8, 161.9 and
164.9 (4 ꢁ C).
2.2.1.5. 2-Amino-4-(2-fluorophenyl)-6-(4-hydroxyphenyl)nicotinonit-
rile (4l). Colorless crystals; m.p = 181–184 °C; IR (KBr): 3352 and
3359 (NH2), 3341 (OH), 2221 (CN) cmꢀ1 1H NMR (400 MHz,
;
2.2.1.11. 2-Amino-4-(3-hydroxyphenyl)-6-(4-hydroxyphenyl)nicoti-
DMSO-d6) d = 6.78 (d, J = 7.9 Hz, 2 H, 2 ꢁ CH), 7.07 (s, 2 H, NH2),
7.28 (s, 1 H, CH), 7.30–750 (m, 4 H, 4 ꢁ CH), 7.63 (d, J = 7.9 Hz, 2
H, 2 ꢁ CH), 9.84 (s, 1 H, OH); 13C NMR (100 MHz, DMSO-d6)
nonitrile (4r). Colorless crystals; m.p = 185–189 °C; IR (KBr): 3353
and 3358 (NH2), 3341 (OH), 2229 (CN) cmꢀ1 1H NMR (400 MHz,
;
DMSO-d6) d = 6.84 (d, J = 8.8 Hz, 2 H, 2 ꢁ CH), 6.87 (s, 2 H, NH2),
6.89 (d, J = 8.0 Hz, 1 H, CH), 6.99 (s, 1 H, CH), 7.02 (d, J = 7.6 Hz, 1
H, CH), 7.11 (s, 1 H, CH), 7.32 (dd, J = 8.0, J = 7.6 Hz, 1 H, CH),
7.97 (d, J = 8.8 Hz, 2 H, 2 ꢁ CH), 9.76 (s, 1 H, OH), 9.93 (s, 1 H,
OH); 13C NMR (100 MHz, DMSO-d6) d = 84.9 (CN), 111.2, 113.8
and 114.6 (3 ꢁ CH), 115.9 (C), 116.4, 118.9 and 126.8 (2 ꢁ CH),
127.2 (C), 128.3, 132.8, 140.8 and 156.9 (4 ꢁ CH), 158.6, 163.7,
164.8 and 165.5 (4 ꢁ C).
3
d = 87.5 (CN), 111.2 (CH), 116.3 (CH), 124.8 (d, C-F, JFC = 8.0 Hz,
CH), 126.5 (CH), 129.2 (C), 129.7 (CH),131.1 (C), 131.9 (d, C-F,
3
2JFC = 22.0 Hz, CH), 132.5 (d, C-F, JFC = 7.9 Hz, C), 136.1 (d, C-F,
1
2JFC = 23.0 Hz, CH), 137.8 (CH), 154.4 (d, C-F, JFC = 244.0 Hz, C),
160.7 and 161.4 (2 ꢁ CH).
2.2.1.6. 2-Amino-4-(2-chlorophenyl)-6-(4-hydroxyphenyl)nicotino-
nitrile (4m). Colorless crystals; m.p = 194–196 °C; IR (KBr): 3354
and 3361 (NH2), 3344 (OH), 2220 (CN) cmꢀ1 1H NMR (400 MHz,
;
2.2.1.12. 2-Amino-4-(4-bromophenyl)-6-(4-hydroxyphenyl)nicotino-
DMSO-d6) d = 6.81 (d, J = 8.2 Hz, 2 H, 2 ꢁ CH), 6.97 (s, 2 H, NH2),
7.07 (s, 1 H, CH), 7.40–7.80 (m, 4 H, 4 ꢁ CH), 7.92 (d, J = 8.2 Hz, 2
H, 2 ꢁ CH), 10.05 (s, 1 H, OH); 13C NMR (100 MHz, DMSO-d6)
d = 85.4 (CN), 108.4 (CH), 115.8 (CH), 117.6 (CH), 123.5 (C), 128.7
(C), 129.4 (C), 130.9 (CH), 132.1 (CH), 136.8 (CH), 153.7, 159.2,
160.1 and 161.2 (4 ꢁ C).
nitrile (4s). Colorless crystals; m.p = 234–237 °C; IR (KBr): 3352
and 3356 (NH2), 3348 (OH), 2231 (CN) cmꢀ1 1H NMR (400 MHz,
;
DMSO-d6) d = 6.83 (d, J = 8.1 Hz, 2 H, 2 ꢁ CH), 6.93 (s, 2 H, NH2),
7.14 (s, 1 H, CH), 7.59 (d, J = 7.9 Hz, 2 H, 2 ꢁ CH), 7.65 (d,
J = 7.9 Hz, 2 H, 2 ꢁ CH), 8.0 (d, J = 8.1 Hz, 2 H, 2 ꢁ CH), 9.93 (s, 1
H, OH); 13C NMR (100 MHz, DMSO-d6) d = 87.9 (CN), 110.9, 116.9
and 124.4 (3 ꢁ CH), 127.3 (C), 128.8 (CH), 129.7 and 130.4
(2 ꢁ C), 132.2 (C), 135.7 (CH), 137.7, 153.8, 160.1 and 160.3 (4 ꢁ C).
2.2.1.7. 2-Amino-4-(3-fluorophenyl)-6-(4-hydroxyphenyl)nicotinonit-
rile (4n). Colorless crystals; m.p = 231–234 °C; IR (KBr): 3353 and
3360 (NH2), 3339 (OH), 2228 (CN) cmꢀ1 1H NMR (400 MHz,
;
DMSO-d6) d = 6.81 (d, J = 9.2 Hz, 2 H, 2 ꢁ CH), 6.81 (s, 2 H, NH2),
7.20 (s, 1 H, CH), 7.36 (t, J = 8.4 Hz, 1 H, CH), 7.40–7.60 (m, 3 H,
3 ꢁ CH), 8.0 (d, J = 9.2 Hz, 2 H, 2 ꢁ CH), 9.94 (s, 1 H, OH); 13C
NMR (100 MHz, DMSO-d6) d = 85.6 (CN), 108.7 (CH), 115.7 (CH),
2.2.1.13. 2-Amino-6-(4-hydroxyphenyl)-4-(4-nitrophenyl)nicotinonit-
rile (4t). Colorless crystals; m.p = 205–208 °C; IR (KBr): 3355 and
3366 (NH2), 3342 (OH), 1350 (N-O), 1510 (N = O), 2219 (CN)
cmꢀ1 1H NMR (400 MHz, DMSO-d6) d = 6.94 (d, J = 8.1 Hz, 2 H,
;
2
115.9 (CH), 116.7 (d, JFC = 21 Hz, C-F, CH), 116.8 (C), 117.6 (CH),
2 ꢁ CH), 6.99 (s, 2 H, NH2), 7.22 (s, 1 H, CH), 7.27 (d, J = 7.8 Hz, 2
H, 2 ꢁ CH), 7.39 (d, J = 7.8 Hz, 2 H, 2 ꢁ CH), 7.75 (d, J = 8.1 Hz, 2
H, 2 ꢁ CH), 9.94 (1 H, s, OH); 13C NMR (100 MHz, DMSO-d6)
d = 86.8 (CN), 112.2, 115.5 and 116.4 (3 ꢁ CH), 122.4 (CH), 128.8
3
125.0 (C), 128.7 (CH), 129.5 (C), 131.1 (d, JFC = 8.0 Hz, C-F, C),
3
139.8 (d, JFC = 8.0 Hz, C-F, CH), 153.4 (CH), 159.3, 160.1 and
1
(3 ꢁ C), 161.2 (CH), 162.5 (d, JFC = 240 Hz, C-F, CH).