96 Zheng et al.
Asian J. Chem.
MS: [M+H]+ = 422.0; Elemental analysis: Calcd. (%): C 62.29,
H 4.09, N 16.27; Found (%): C 62.64, H 4.06, N 16.60.
Compound 6b: m.p.: 259-263 °C; IR (KBr, νmax, cm-1):
1697 (C=O); 1H NMR (DMSO-d6) δ: 2.17 (s, 3H, CH3), 2.20
(s, 3H, CH3), 7.05 (d, 1H, J = 8.2 Hz, Ar-H), 7.21 (s, 1H, Ar-
H), 7.30 (d, 1H, J = 1.9 Hz, Ar-H), 7.43 (t, 1H, Ar-H), 7.76 (d,
1H, J = 8.9 Hz, Ar-H), 7.82 (m, 1H, Ar-H), 7.86(t, 1H, Ar-H),
8.16 (dd, 1H, J1 = 2.6 Hz, J2 = 2.6 Hz, Ar-H), 8.49 (d, 1H, J =
2.2 Hz,Ar-H), 8.53, 8.68, 8.89 (s, each 1H, 3 × NH); 13C NMR
(DMSO-d6) δ: 18.6, 19.5, 109.6, 115.4, 115.8, 116.3, 116.4,
119.6, 122.5, 122.5, 123.6, 126.4, 128.4, 129.6, 129.6, 136.3,
136.7, 137.1, 137.8, 145.7, 152.3, 152.5, 156.9. MS: [M+H]+
= 436.0; Elemental analysis: Calcd. (%): C 62.91, H 4.45, N
15.97; Found (%): C 63.38, H 4.39, N 16.07.
Compound 6g: m.p.: 265-268 °C; IR (KBr, νmax, cm-1):
1706 (C=O); 1H NMR (DMSO-d6) δ: 7.27-7.37 (m, 2H, Ar-
H), 7.62-7.71 (m, 2H, Ar-H), 7.78 (d, 1H, J = 8.9 Hz, Ar-H),
7.88 (t, 2H,Ar-H), 8.19 (d, 2H, J = 2.0 Hz,Ar-H), 8.54 (d, 1H,
J = 1.6 Hz, Ar-H), 8.57 (s, 1H, Ar-H), 9.16, 9.38, 9.86 (s, each
1H, 3 × NH); 13C NMR (DMSO-d6) δ: 110.8, 115.5, 116.8,
116.9, 120.8, 120.9, 122.5, 123.0, 123.1, 124.2, 125.7, 126.8,
128.4, 130.1, 131.9, 137.0, 139.1, 141.1, 146.1, 152.4, 152.6,
157.0. MS: [M+H]+ = 536.1; Elemental analysis: Calcd. (%):
C 49.11, H 2.61, N 12.58; Found (%): C 49.23, H 2.63, N
113.05.
Compound 6h: m.p.: 214-220 °C; IR (KBr, νmax, cm-1):
1686 (C=O); 1H NMR (DMSO-d6) δ: 7.40 (dd,4H, J1 = 8.8
Hz, J2 = 5.0 Hz), 7.55 (d, 2H, J = 8.8 Hz, Ar-H), 7.78-7.85 (m,
2H, Ar-H)), 7.97 (t, 2H, Ar-H), 8.09(s, 1H, Ar-H), 8.70 (d,
2H, Ar-H), 9.44, 9.47, 10.72 (s, each 1H, 3 × NH); 13C NMR
(DMSO-d6) δ: 110.4, 114.9, 119.8, 121.0, 122.2, 124.5, 125.6,
125.7, 127.3, 127.6, 128.5, 130.3, 138.4, 138.7, 139.8, 150.6,
152.4, 158.1. MS: [M+H]+ = 468.0; Elemental analysis: Calcd.
(%): C 53.72, H 3.59, N 14.82; Found (%): C 53.81, H 3.23,
N 14.94.
Compound 6c: m.p.: 226-230 °C; IR (KBr, νmax, cm-1):
1697 (C=O);1H NMR (DMSO-d6) δ: 7.41 (t, 1H, Ar-H), 7.63
(d, 1H, J = 8.8 Hz, Ar-H), 7.71 (dd, 2H, J1 = 2.2 Hz, J2 = 2.1
Hz, Ar-H), 7.82-7.85 (m, 1H, Ar-H), 7.94 (d, 1H, J = 2.0 Hz,
Ar-H), 8.12 (d, 1H, J = 2.4 Hz, Ar-H), 8.20 (dd, 1H, J1 = 2.6
Hz, J2 = 2.6 Hz, Ar-H), 8.44 (d, 1H, J = 9.1 Hz, Ar-H), 8.57 (s,
1H, Ar-H), 9.17, 9.34, 9.76 (s, each 1H, 3 × NH). 13C NMR
(DMSO-d6) δ: 110.7, 115.4, 116.2, 116.5, 116.8, 116.9, 116.9,
122.6, 122.7, 123.2, 123.7, 124.6, 126.9, 128.5, 131.99, 136.6,
136.7, 137.1, 139.2, 146.1, 152.4, 152.6, 157.0. MS: [M+H]+
= 510.0; Elemental analysis: Calcd. (%): C 51.95, H 3.84, N
14.18; Found (%): C 51.78, H 3.57, N 13.73.
Compound 6i: m.p.: 249-252 °C; IR (KBr, νmax, cm-1):
1655 (C=O); 1H NMR (DMSO-d6) δ: 5.25 (s, 2H, -CH2-), 7.15-
7.21 (m, 1H, Ar-H), 7.27 (t, 2H, Ar-H), 7.33 (t, 3H, Ar-H),
7.46 (dd, 1H, J1 = 6.0 Hz, J2 = 6.1 Hz, Ar-H), 7.53 (t, 2H, Ar-
H), 7.70 (dd, 2H, J1 = 2.4 Hz, J2 = 8.9 Hz, Ar-H), 7.84 (dd,
1H, J1 = 1.6 Hz, J2 = 1.7 Hz, Ar-H), 8.00 (t, 1H, Ar-H), 8.47 (t,
2H, Ar-H), 8.97, 9.02, 9.73 (s, each 1H, 3 × NH); 13C NMR
(DMSO-d6) δ: 69.4, 110.3, 113.7, 114.0, 114.3, 114.6, 115.3,
119.8, 121.0, 122.2, 123.1, 124.0, 125.5, 126.4, 128.3, 128.5,
130.3, 130.4, 133.5, 137.2, 138.4, 145.7, 149.4, 152.4, 152.6,
157.0, 160.5, 163.7. MS: [M+H]+ = 548.0; Elemental analysis:
Calcd. (%): C 60.89, H 3.73, N 12.52; Found (%): C 61.32, H
3.68, N 12.77.
Compound 6d: m.p.: 260-264 °C; IR (KBr, νmax, cm-1):
1657(C=O); 1H NMR (DMSO-d6) δ: 7.33-7.38 (m, 2H, Ar-
H), 7.44 (t, 1H, Ar-H), 7.52-7.56 (m, 2H, Ar-H), 7.79 (t, 1H,
Ar-H), 7.80-7.88 (m, 2H, Ar-H), 8.15-8.19 (m, 1H, Ar-H),
8.50 (d, 1H, J = 2.1 Hz, Ar-H), 8.55, 9.01, 9.86 (s, each 1H, 3
× NH); 13C NMR (DMSO-d6) δ: 110.2, 115.4, 116.1, 116.4,
119.7, 119.8, 122.4, 122.5, 123.4, 123.6, 125.5, 126.5, 126.6,
128.4, 128.5, 136.7, 137.4, 138.4, 145.8, 152.4, 156.9. MS:
[M+H]+ = 442.0; Elemental analysis: Calcd. (%): C 56.66, H
3.10, N 15.57; Found (%): C 57.03, H 3.19, N 15.83.
Compound 6j: m.p.: 240-242 °C; IR (KBr, νmax, cm-1):
1707 (C=O); 1H NMR (DMSO-d6) δ: 5.26 (s, 2H, -CH2-), 7.15-
7.34 (m, 4H, Ar-H), 7.44-7.51 (m, 1H, Ar-H), 7.62-7.85 (m,
5H, Ar-H), 7.99 (d, 1H, J = 2.5Hz, Ar-H), 8.20 (d, 1H, J =
2.2Hz, Ar-H), 8.50 (s, 2H,Ar-H), 9.13, 9.38, 9.77 (s, each 1H,
3 × NH); 13C NMR (DMSO-d6) δ: 69.4, 110.8, 113.7, 114.0,
114.3, 114.6, 115.3, 116.8, 116.9, 122.3, 123.1, 123.2, 124.1,
126.6, 128.3, 130.3, 130.4, 131.9, 133.4, 136.8, 139.1, 145.9,
149.5, 152.4, 152.8, 157.1, 160.5, 163.7. MS: [M+H]+ = 616.0;
Elemental analysis: Calcd. (%): C 56.07, H 3.00, N 11.05;
Found (%): C 56.51, H 3.11, N 11.36.
Compound 6e: m.p.: >250 °C; IR (KBr, νmax, cm-1): 1634
(C=O);1H NMR (DMSO-d6) δ: 7.28-7.30 (m, 1H,Ar-H), 7.35
(t, 1H, Ar-H), 7.76 (t, 1H, Ar-H), 7.78 (d, 1H, J = 8.9 Hz, Ar-
H), 7.84-7.89 (m, 3H, Ar-H), 8.19 (t, 1H, Ar-H), 8.56 (t, 2H,
Ar-H), 8.65 (t, 1H, Ar-H), 9.14, 9.43, 9.85 (s, each 1H, 3 ×
NH); 13C NMR (DMSO-d6) δ: 110.7, 112.2, 115.5, 116.5,
120.9, 121.1, 124.3, 124.4, 125.8, 126.8, 128.5, 130.1, 130.2,
137.1, 140.9, 141.1, 146.1, 148.1, 152.5, 152.6, 157.0. MS:
[M+H]+ = 510.0; Elemental analysis: Calcd. (%): C 52.41, H
3.07, N 17.19; Found (%): C 52.63, H 3.15, N 17.53.
RESULTS AND DISCUSSION
Compound 6f: m.p.: 248-250 °C; IR (KBr, νmax, cm-1):
1697(C=O); 1H NMR (DMSO-d6) δ: 2.17 (s, 3H, CH3), 2.21
(s, 3H, CH3), 7.05 (d, 1H, J = 8.2 Hz, Ar-H), 7.21 (dd, 1H, J1
= 2.1 Hz, J2 = 2.0 Hz, Ar-H), 7.27-7.30 (m, 2H, Ar-H), 7.36 (t,
1H, Ar-H), 7.77 (d, 1H, J = 8.9 Hz, Ar-H), 7.88 (dd, 2H, J1 =
1.7 Hz, J2 = 1.6 Hz, Ar-H), 8.19 (s, 1H, Ar-H), 8.49 (d, 1H, J
= 2.1 Hz, Ar-H), 8.56 (s, 1H, Ar-H), 8.69, 8.89, 9.83 (s, each
1H, 3 × NH); 13C NMR (DMSO-d6) δ: 18.6, 19.5, 109.8, 115.6,
115.9, 119.6, 120.7, 121.0, 124.1, 125.7, 126.5, 128.4, 129.6,
129.6, 130.2, 136.3, 137.1, 137.8, 141.0, 145.8, 152.3, 152.5,
156.9. MS: [M+H]+ = 462.0; Elemental analysis: Calcd. (%): C
59.34, H 4.26, N 14.89; Found (%): C 59.75, H 4.36, N 115.15.
The synthesis of 4-anilinoquinazoline derivates (6a-j) is
outlined in Scheme-I, which started with 2-amino-5-nitro-
benzoic acid. We investigated the reaction between 2-amino-
5-nitrobenzoic acid (1) and formamidine acetate in ethylene
glycol monomethyl ether [under reflux for 30 h or pressurized
microwave irradiation for 1 h. Compound (2) was chloridated
by thionyl chloride to give compound (3), which was astable
due to theelectro attracting group nitro in the C6. Compound 4
was obtained after a reaction of amination between compound
3 and aniline in 75-88 % yields. Reduction of compound 4
used Rany Ni/H2 in alcohol to achieve compound 5, which