K. M. El-Shaieb – P. G. Jones · Synthesis of 2-(2-Aminophenyl)-4-arylquinazoline Derivatives
949
1568, 1548, 1511 cm−1 (C=C). – 1H NMR (400 MHz, 6.77 – 6.74 (dd, 1 H, J = 1.01, 8.17 Hz, 15-H), 6.61 – 6.54
[D6]DMSO): δ = 9.97 (s, 1 H, NH), 8.51 (d, 1 H, J = 8.27 Hz, (m, 1 H, 13-H), 2.35 (s, 3 H, CH3). – 13C NMR (100 MHz,
19-H), 8.42 (d, 1 H, J = 2.40 Hz, 22-H), 8.34 – 8.29 (dd, 1 H, [D6]DMSO): δ = 161.30 (C-4), 157.05 (C-2), 150.01 (C-9),
J = 1.50, 8.10 Hz, 18-H), 7.87 – 7.83 (m, 2 H), 7.47 (br, s, 149.51 (C-12), 136.56 (C-18), 133.06 (CH, C-7), 132.91
2 H, NH2), 7.23 – 7.14 (m, 2 H), 6.86 – 6.82 (m, 2 H), 6.64 – (CH, C-14), 130.87 (CH, C-5), 130.48 (CH, C-8), 128.97
6.56 (m, 2 H). – 13C NMR (100 MHz, [D6]DMSO): δ = (2 CH, C-20,22), 127.44 (CH, C-13), 125.36 (CH, C-6),
160.98 (C), 156.59 (C), 150.09 (C), 149.51 (C), 139.53 (C), 122.90 (CH, C-16), 122.69 (2 CH, C-19,23), 117.68 (C-21),
133.37 (CH), 131.08 (C), 130.68 (CH), 130.33 (CH), 130.25 116.42 (C-10), 114.60 (CH, C-15), 113.11 (C-11), 20.57
(CH), 127.54 (CH), 125.71 (CH), 124.73 (C), 123.27 (CH), (CH3). – MS (EI, 70 eV): m/z (%) = 326 (100) [M]+, 325
122.84 (CH), 121.79 (CH), 117.33 (C), 116.54 (CH), 114.69 (86) [M–1]+, 309 (4) [M–NH3]+, 232 (8) [M–PhNH2]+,
(CH), 113.66 (C). – MS (EI, 70 eV): m/z (%) = 384 (10) 220 (12), 208 (48), 192 (16), 180 (8), 163 (16), 129 (4), 118
[M]+4, 382 (52) [M]+2, 380 (86) [M]+, 364 (4) [M–NH2]+, (16), 102 (4), 92 (16), 75 (12). – C21H18N4 (326.39): calcd.
330 (30) [M–(Cl+NH2)]+, 294 (4), 261 (24), 245 (12), 220 C 77.28, H 5.56, N 17.17; found C 77.02, H 5.51, N 16.94.
(6), 192 (10), 166 (12), 155 (24), 141 (18), 118 (16), 92 (12),
75 (8). – C20H14Cl2N4 (381.26): calcd. C 63.01, H 3.70,
Cl 18.60, N 14.70; found C 62.78, H 3.67, Cl 18.39, N 14.46.
2-(2-Aminophenyl)-N-(4-methoxyphenyl)quinazolin-4-
amine (5g)
Brown solid, 60 mg (70 %), m. p. 131 – 133 ◦C. – IR
(film): ν = 3385, 3277, 3243 (NH, NH2), 1610 (C=N), 1559,
1535, 1505 cm−1 (C=C). – 1H NMR (400 MHz, CDCl3):
2-(2-Aminophenyl)-N-(2,4-dimethylphenyl)quinazolin-4-
amine (5e)
◦
Pale-yellow solid, 65 mg (76 %), m. p. 155 – 157 C. – δ = 7.92 – 7.86 (m, 2 H), 7.77 – 7.62 (m, 2 H), 7.49 – 7.42
IR (film): ν = 3431, 3376, 3226 (NH, NH2), 1684, 1611 (m, 1 H), 7.44 (br, s, 1 H, NH), 7.31 – 7.22 (m, 2 H), 7.01 –
(C=N), 1574, 1504 cm−1 (C=C). – 1H NMR (400 MHz, 6.93 (m, 1 H), 6.79 – 6.62 (m, 4 H), 5.71 (br, s, 2 H, NH2),
[D6]DMSO): δ = 9.71 (s, 1 H, NH), 8.52 (d, 1 H, J = 8.09 Hz, 3.73 (s, 3 H, OCH3). – 13C NMR (100 MHz, CDCl3): δ =
8-H), 8.22 (d, 1 H, J = 7.00 Hz, 5-H), 7.81 (d, 1 H, J = 162.03 (C-4), 151.75 (C-2), 150.39 (C-21), 147.15 (C-9),
3.71 Hz, 22-H), 7.77 – 7.73 (m, 1 H, 7-H), 7.57 – 7.49 (m, 140.43 (C-12), 139.52 (C-18), 134.65 (C-10), 133.93 (CH,
1 H, 6-H), 7.33 (d, 1 H, J = 7.88 Hz, 19-H), 7.26 – 7.21 (m, C-7), 131.19 (2 CH, C-19,23), 127.09 (CH, C-14), 126.40
1 H, 20-H), 7.15 (d, 1 H, J = 7.73 Hz, 16-H), 7.10 (br, s, (CH, C-5), 124.16 (CH, C-8), 122.27 (CH, C-13), 116.63
2 H, NH2), 6.81 (d, 1 H, J = 8.47 Hz, 14-H), 6.75 – 6.70 (m, (2 CH, C-20,22), 116.19 (CH, C-6), 114.78 (CH, C-16),
1 H, 15-H), 6.60 – 6.46 (m, 1 H, 13-H), 2.35 (s, 3 H, CH3), 114.14 (CH, C-15), 109.36 (C-11), 55.70 (OCH3). – MS (EI,
2.12 (s, 3 H, CH3). – 13C NMR (100 MHz, [D6]DMSO): 70 eV): m/z (%) = 342 (62) [M]+, 325 (4) [M–NH3]+, 294
δ = 167.36 (C-4), 161.38 (C-2), 158.21 (C-9), 151.29 (C-12), (4) [M–(NH2+OCH3)]+, 251 (6) (M–PhNH2]+, 192 (10),
149.91 (C-18), 135.34 (C-10), 134.55 (C-23), 133.83 (CH, 163 (8), 129 (4), 118 (16), 102 (4), 92 (16), 75 (12). –
C-7), 131.09 (CH, C-14), 130.66 (CH, C-5), 130.53 (CH, C21H18N4O (342.39): calcd. C 73.67, H 5.30, N 16.36; found
C-8), 128.22 (CH, C-13), 127.26 (CH, C-6), 126.75 (C-21), C 77.43, H 5.23, N 16.12.
122.94 (CH, C-20), 117.77 (CH, C-19), 116.45 (CH, C-22),
114.62 (CH, C-16), 112.77 (CH, C-15), 108.93 (C-11), 20.60
(CH3), 17.88 (CH3). – MS (EI, 70 eV): m/z (%) = 341 (30)
[M]+1, 340 (100) [M]+, 324 (8) [M–NH2]+, 309 (30) [M–
(CH3+NH2)]+, 294 (6), 272 (40), 245 (2), 220 (16), 192 (16),
166 (12), 155 (34), 141 (8), 118 (16), 92 (20), 75 (12). –
C22H20N4 (340.42): calcd. C 77.62, H 5.92, N 16.46; found
C 77.41, H 5.87, N 16.28.
2-(2-Aminophenyl)-N-(3-methoxyphenyl)quinazolin-4-
amine (5h)
◦
Pale-brown solid, 58 mg (68 %), m. p. 93 – 95 C. – IR
(film): ν = 3378, 3287, 3253 (NH, NH2), 1615 (C=N), 1545,
1523, 1500 cm−1 (C=C). – 1H NMR (400 MHz, CDCl3):
δ = 7.79 – 7.68 (m, 2 H), 7.66 – 7.60 (m, 2 H), 7.53 – 7.48
(m, 1 H), 7.47 (br, s, 1 H, NH), 7.31 – 7.22 (m, 2 H), 7.01 –
6.93 (m, 1 H), 6.79 – 6.62 (m, 4 H), 5.73 (br, s, 2 H, NH2),
3.79 (s, 3 H, OCH3). – 13C NMR (100 MHz, CDCl3): δ =
2-(2-Aminophenyl)-N-p-tolylquinazolin-4-amine (5f)
◦
Colorless solid, 62 mg (76 %), m. p. 159 – 160 C. – IR 161.32 (C-4), 151.57 (C-2), 151.43 (C-21), 147.61 (C-9),
(film): ν = 3357, 3287, 3211 (NH, NH2), 1608 (C=N), 141.03 (C-12), 139.52 (C-18), 134.65 (C-10), 133.93 (CH,
1573, 1552, 1511 cm−1 (C=C). – 1H NMR (400 MHz, C-7), 131.19 (2 CH, C-19,23), 127.09 (CH, C-14), 126.40
[D6]DMSO): δ = 9.77 (s, 1 H, NH), 8.51 (d, 1 H, J = 8.33 Hz, (CH, C-5), 124.16 (CH, C-8), 122.27 (CH, C-13), 116.63
8-H), 8.33 – 8.30 (dd, 1 H, J = 1.59, 8.07 Hz, 5-H), 7.87 – (2 CH, C-20,22), 116.19 (CH, C-6), 114.78 (CH, C-16),
7.81 (m, 2 H, 6,7-H), 7.73 (d, 2 H, J = 8.40 Hz, 20,22-H), 114.14 (CH, C-15), 109.36 (C-11), 55.89 (OCH3). – MS (EI,
7.58 – 7.53 (m, 1 H, 16-H), 7.36 (br, s, 2 H, NH2), 7.26 (d, 70 eV): m/z (%) = 342 (40) [M]+, 326 (12) [M–NH2]+, 296
2 H, J = 8.26 Hz, 19,23-H), 7.14 – 7.09 (m, 1 H, 14-H), (4), 250 (8) [M–PhNH2]+, 220 (2), 208 (6), 192 (12), 182
Unauthenticated
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