5
3.1.10 2-Methyl-3-(3,4,5-trimethoxyphenyl)quinazolin-4(3H)-one
(3j).
1H), 7.82 (d, J = 1.6 Hz, 1H), 7.55-7.46 (m, 4H), 7.22 (d, J =
ACCEPTED MANUSCRIPT
7.2 Hz, 2H), 2.20 (s, 3H); 13C NMR (CDCl3, 100 MHz): δ =
161.7, 155.6, 148.4, 137.4, 130.0, 129.9, 129.5, 129.4, 129.2,
128.4, 127.8, 119.5, 24.4; HRMS (ESI-TOF) calcd. for
C15H1279BrN2O [M+H]+ m/z = 315.0133, found 315.0135; HRMS
(ESI-TOF) calcd. for C15H1281BrN2O [M+H]+ m/z = 317.0113,
found 317.0122.
o
(60 mg, 52%) as a pale brown solid; mp 120-121 C; IR (KBr):
1
1723, 1674 cm–1; H NMR (CDCl3, 400 MHz): δ = 8.23 (d, J =
8.0 Hz, 1H), 7.74 (t, J = 8.0 Hz, 1H), 7.66 (d, J = 8.0 Hz, 1H),
7.44 (t, J = 7.6 Hz, 1H), 6.45 (s, 2H), 3.88 (s, 3H), 3.82 (s, 6H),
2.31 (s, 2H); 13C NMR (CDCl3, 100 MHz): δ = 162.1, 154.5,
154.1, 147.0, 138.5, 134.7, 133.1, 127.0, 126.7, 126.5, 120.5,
105.1, 60.9, 56.2, 23.8; HRMS (ESI-TOF) calcd for C18H19N2O4
[M+H]+ m/z = 327.1345, found: 327.1346.
3.1.16
(3q).
6,7-dimethoxy-2-methyl-3-phenylquinazolin-4(3H)-one
o
(105 mg, 68%) as a brown solid; mp 240-241 C; IR (KBr):
1
3.1.11 2-Propyl-3-(p-tolyl)quinazolin-4(3H)-one (3k).
1675, 1614 cm-1; H NMR (CDCl3, 400 MHz): δ 7.53-7.44 (m,
4H), 7.23 (d, J = 7.2 Hz, 2H), 7.06 (s, 1H), 3.97 (s, 3H), 3.93 (s,
3H), 2.18 (s, 3H); 13C NMR (CDCl3, 100 MHz): δ = 161.5,
155.1, 152.9, 148.8, 143.5, 137.8, 129.8, 129.1, 128.0, 113.8,
107.1, 105.9, 56.3, 56.2, 24.0; HRMS (ESI-TOF) calcd. for
C17H17N2O3 [M+H]+ m/z = 297.1239, found 297.1237.
(76.2 mg, 56%) as a yellow solid; mp 151-152 oC; IR (CaF2):
1
1682, 1594 cm–1; H NMR (CDCl3, 400 MHz): δ = 8.24 (d, J =
8.0 Hz, 1H), 7.75-7.67 (m, 2H), 7.44-7.40 (m, 1H), 7.32 (d, J =
7.8 Hz, 2H), 7.10 (d, J = 8.0 Hz, 2H), 2.43-2.38 (m, 5H), 1.70 (q,
J = 7.5 Hz, 2H), 0.85 (t, J = 7.2 Hz, 3H); 13C NMR (CDCl3, 100
MHz): δ = 162.5, 157.1, 147.4, 139.2, 134.6, 134.3, 130.4, 127.9,
127.0, 126.9, 126.4, 120.7, 37.6, 21.2, 20.5, 13.7; HRMS (ESI-
TOF) calcd for C18H19N2O [M+H]+ m/z = 279.1497, found
279.1501.
3.1.17 2-methyl-3-(o-tolyl)quinazolin-4(3H)-one (3r).13a
(473 mg, 78%) as a white solid; mp 114-115 oC; IR (KBr): 1683,
1598 cm-1; 1H NMR (CDCl3, 400 MHz): δ 8.24 (dd, J = 8.0, 1.2
Hz, 1H), 7.72 (ddd, J = 15.2, 7.6, 1.6 Hz, 1H), 7.65 (dd, J = 8.0,
0.4 Hz, 1H), 7.42 (ddd, J = 15.0, 7.6, 0.8 Hz, 1H), 7.37-7.30 (m,
3H), 7.12 (d, J = 7.2 Hz, 1H), 2.14 (s, 3H), 2.09 (s, 3H); 13C
NMR (CDCl3, 100 MHz): δ = 161.4, 154.1, 147.5, 136.6, 135.2,
134.4, 131.3, 129.4, 127.8, 127.5, 126.9, 126.6, 126.4, 120.6,
23.7, 17.2; HRMS (ESI-TOF) calcd. for C16H15N2O [M+H]+ m/z
= 251.1184, found 251.1181.
3.1.12 2-Isopropyl-3-(p-tolyl)quinazolin-4(3H)-one (3l).
(55.2 mg, 41%) as an orange solid; mp 151-152 oC; IR (CaF2):
1
1682, 1604 cm–1; H NMR (CDCl3, 400 MHz): δ = 8.24 (d, J =
7.6 Hz, 1H), 7.78-7.74 (m, 2H), 7.45-7.41 (m, 1H), 7.33 (br, 2H),
7.13 (br, 2H), 2.7 (br, 1H), 2.4 (s, 3H), 1.24 (d, J = 2.0 Hz, 6H);
13C NMR (CDCl3, 100 MHz): δ = 162.6, 162.1, 147.3, 139.2,
134.6, 134.4, 130.5, 128.0, 127.0, 126.9, 126.5, 120.7, 32.3, 21.3;
HRMS (ESI-TOF) calcd for C18H19N2O [M+H]+ m/z = m/z
279.1497, found 279.1506.
3.1.18 3-([1,1'-biphenyl]-3-yl)-2-methylquinazolin-4(3H)-one
(3s).
1
(89 mg, 81%) as a colorless viscous oil; H NMR (CDCl3, 400
3.1.13 2-Phenyl-3-(p-tolyl)quinazolin-4(3H)-one (3m).13c
MHz): δ = 8.29-8.26 (m, 1H), 7.69 (ddd, J = 15.6, 7.6, 1.6 Hz,
1H), 7.54-7.49 (m, 4H), 7.42 (ddd, J = 15.6, 7.4, 1.2 Hz, 1H),
7.29-7.25 (m, 3H), 7.21-7.18 (m, 3H), 2.03 (s, 3H); 13C NMR
(CDCl3, 100 MHz): δ = 162.9, 154.0, 147.4, 140.3, 137.8, 135.3,
134.4, 131.5, 129.7, 129.0, 128.8, 128.5, 128.1, 127.8, 127.1,
126.6, 126.4, 120.3, 23.9; HRMS (ESI-TOF) calcd for
C21H17N2O [M+H]+ m/z = 313.1341, found 313.1341.
(72.6 mg, 48%) as a pale yellow solid; mp 185-186 oC; IR
1
(CaF2): 1685, 1604 cm–1; H NMR (CDCl3, 400 MHz): δ = 8.26
(d, J = 7.9 Hz, 1H), 7.75-7.69 (m, 2H), 7.45-7.41 (m, 1H), 7.27-
7.25 (m, 2H), 7.19-7.11 (m, 3H), 7.02 (d, J = 8.1 Hz, 2H), 6.94
(d, J = 8.2 Hz, 2H), 2.21 (s, 3H); 13C NMR (CDCl3, 100 MHz): δ
= 162.3, 155.3, 147.4, 138.2, 135.5, 134.9, 134.6, 129.6, 129.2,
128.9, 128.7, 127.9, 127.6, 127.1, 120.9, 21.1; HRMS (ESI-TOF)
calcd for C21H17N2O [M+H]+ m/z = 313.1341, found 313.1335.
3.1.19 ethyl 2-(4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)
acetate (3t) and ethyl 2-(4-oxo-3-phenyl-3,4-dihydroquinolin-
2(1H)-ylidene)acetate (3t’).
3.1.14 2-Benzyl-3-(p-tolyl)quinazolin-4(3H)-one (3n).13d
(108 mg, 68%) as a pale yellow viscous oil; (3t : 3t’= 1: 0.33
inseparable mixture); Compound 3t: 1H NMR (CDCl3, 400
MHz): δ = 8.28-8.26 (m, 1H), 7.70 (ddd, J = 15.2, 7.6, 1.6 Hz,
1H), 7.71-7.69 (m, 1H), 7.56-7.53 (m, 1H), 7.52-7.51 (m, 1H),
7.51-7.50 (m, 1H), 7.49-7.48 (m, 1H), 7.27-7.25 (m, 1H), 7.24-
7.23 (m, 1H), 4.07-4.03 (m, 2H), 3.58 (s, 2H), 1.16 (t, J = 7.2 Hz,
3H); 13C NMR (CDCl3, 100 MHz): δ = 167.8, 150.2, 147.2,
136.9, 134.6, 130.1, 129.9, 129.6, 128.5, 128.4 (2C), 127.2,
1
(84.0 mg, 53%) as a yellow oil; IR (CaF2): 1684, 1593 cm-1; H
NMR (CDCl3, 400 MHz): δ = 8.27-8.25 (m, 1H), 7.77-7.75 (m,
2H), 7.48-7.44 (m, 1H), 7.18-7.14 (m, 5H), 6.89-6.87 (m, 2H),
6.82 (d, J = 8.2 Hz, 2H), 3.90 (s, 2H), 2.40 (s, 3H); 13C NMR
(CDCl3, 100 MHz): δ = 162.6, 155.5, 147.4, 139.1, 135.4, 134.4,
134.2, 130.0, 128.6, 128.3, 128.3, 127.2, 127.0, 126.8, 126.8,
120.9, 42.6, 21.2; HRMS (ESI-TOF) calcd. for C22H19N2O
[M+H]+ m/z = 327.1497, found 327.1505.
1
127.0, 61.5, 42.9, 14.0. Compound 3t’ H NMR (CDCl3, 400
MHz): δ = 12.15 (brs, 0.33 H), 8.05-8.03 (m, 0.33 H), 7.59-7.56
(m, 0.32 H), 7.47-7.46 (m, 0.62 H), 7.22-7.21 (m, 0.33 H), 7.11
(ddd, J = 15.2, 7.8, 1.2 Hz, 0.34 H), 7.06 (d, J = 8.4 Hz, 0.34 H),
4.11-4.08 (m, 0.67 H), 1.20 (t, J = 7.2 Hz, 1H); 13C NMR
(CDCl3, 100 MHz): δ = 170.9, 162.2, 160.2, 153.6, 139.4, 135.7,
135.4, 129.3, 128.3, 127.3, 122.6, 121.1, 115.1, 114.8, 59.3, 14.4;
3.1.14 2,6-Dimethyl-3-(p-tolyl)quinazolin-4(3H)-one (3o).
o
(118.1 mg, 92%) as a pale yellow solid; mp 121-122 C; IR
1
(KBr): 1676, 1596 cm-1; H NMR (CDCl3, 400 MHz): δ = 8.00
(d, J = 0.6 Hz, 1H), 7.53-7.52 (m, 2H), 7.31 (d, J = 8.4 Hz, 2H),
7.10 (d, J = 8.2 Hz, 2H), 2.43 (s, 3H), 2.40 (s, 3H), 2.19 (s, 3H);
13C NMR (CDCl3, 100 MHz): δ = 162.3, 153.4, 145.4, 139.1,
136.5, 135.8, 135.1, 130.5, 127.6, 126.4, 126.3, 120.4, 24.2,
21.1(2C); HRMS (ESI-TOF) calcd. for C17H17N2O [M+H]+ m/z =
265.1314, found 265.1354.
HRMS (ESI-TOF) calcd for C18H17N2O3 [M+H]+ m/z
309.1239, found 309.1234.
=
3.2 Crysatllography.
Crystals suitable for X-ray determination were obtained for 3r by
slow evaporization of a chloroform solution at room temperature.
Cell parameters were determined by a Siemens SMART CCD
3.1.15 7-Bromo-2-methyl-3-phenylquinazolin-4(3H)-one (3p).
(103 mg, 63%) as a white solid; mp 173-174 oC; IR (KBr): 1682,
1
1585 cm-1; H NMR (CDCl3, 400 MHz):
δ
= 8.01 (d, J = 8.4 Hz,