Molecules 2018, 23, 2925
8 of 16
1H-NMR (400 MHz, CDCl3):
δ
11.6 (br s, 1H), 8.16 (d, J = 8.1 Hz, 1H), 7.47 (br s, 1H), 7.29 (dd, J =
8.1, 1.0 Hz, 1H), 2.57 (s, 3H), 2.51 (s, 3H); 13C-NMR (101 MHz, CDCl3):
δ 163.9, 153.2, 149.5, 146.0,
128.0, 126.8, 126.1, 117.9, 22.1, 22.0; HRMS (ESI): m/z for C10H10N2O [M + 1]+: calcd.: 175.0871; found:
175.0867.
2-Ethyl-7-methylquinazolin-4(3H)-one
2-amino-4-methylbenzamide (100 mg, 0.67 mmol), triethyl orthopropionate (236 mg, 269
1.34 mmol) and acetic acid (121 mg, 115
L, 2.01 mmol) in absolute ethanol (2 mL) at 110 ◦C for 24
h. Yield: 114 mg (91%) as a white solid, m.p. 244–245 C; IR (CHCl3): 3178, 1674 cm−1; H-NMR
(400 MHz, CDCl3): 11.2 (br s, 1H), 8.17 (d, J = 8.1 Hz, 1H), 7.50 (br s, 1H), 7.30 (dd, J = 8.1, 0.9 Hz,
(8b).
This compound was prepared from
µL,
µ
◦
1
δ
1H), 2.80 (q, J = 7.6 Hz, 2H), 2.51 (s, 3H), 1.43 (t, J = 7.6 Hz, 3H); 13C-NMR (101 MHz, CDCl3):
δ 163.8,
157.4, 149.5, 145.8, 128.0, 127.0, 126.1, 118.2, 29.2, 22.0, 11.5; HRMS (ESI): m/z for C11H12N2O [M + 1]+:
calcd.: 189.1028; found: 189.1031.
7-Methyl-2-phenylquinazolin-4(3H)-one
2-amino-4-methylbenzamide (100 mg, 0.67 mmol), triethyl orthobenzoate (300 mg, 303
1.34 mmol) and acetic acid (121 mg, 115
L, 2.01 mmol) in absolute ethanol (2 mL) at 110 ◦C for 48 h.
Yield: 133 mg (84%) as a light yellow solid, m.p. 239–241 ◦C (lit [40] m.p. 240–241 ◦C); IR (CHCl3):
3156, 1672 cm−1; 1H-NMR (400 MHz, CDCl3):
10.9 (br s, 1H), 8.21 (d, J = 8.1 Hz, 1H), 8.18 (m, 2H),
7.64 (br s, 1H), 7.61–7.56 (complex, 3H), 7.33 (dd, J = 8.2, 0.9 Hz, 1H), 2.54 (s, 3H); 13C-NMR (101 MHz,
CDCl3): 163.3, 151.6, 149.6, 146.0, 132.9, 131.6, 1291, 128.5, 127.8, 127.2, 126.2, 118.5, 22.0; HRMS (ESI):
m/z for C15H12N2O [M + 1]+: calcd.: 237.1028; found: 237.1023.
(
8d).
This compound was prepared from
µL,
µ
δ
δ
6-Chloro-2-methylquinazolin-4(3H)-one 10a). This compound was prepared from
(
2-amino-5-chlorobenzamide (100 mg, 0.59 mmol) triethyl orthoacetate (191 mg, 216
µ
L, 1.18 mmol)
◦
and acetic acid (106 mg, 101
µ
L, 1.77 mmol) in ◦absolute ethanol (3 mL) at 110 C for 24 h. Yield:
◦
106 mg (92%) as a light tan powder, m.p. 288–290 C (lit [49] m.p. 289–291 C); IR (CHCl3): 3166, 1693,
1
1631 cm−1; H-NMR (400 MHz, CDCl3):
δ 12.4 (br s, 1H), 8.00 (d, J = 2.5 Hz, 1H), 7.79 (dd, J = 8.7,
2.5 Hz, 1H), 7.59 (d, J = 8.7 Hz, 1H), 2.35 (s, 3H); 13C-NMR (101 MHz, DMSO-d6):
δ 160.7, 154.9, 147.7,
134.4, 130.1, 128.9, 124.7, 121.9, 21.5; HRMS (ESI): m/z for C9H735ClN2O [M + 1]+: calcd.: 195.0325;
found: 195.0323.
6-Chloro-2-ethylquinazolin-4(3H)-one
2-amino-5-chlorobenzamide (100 mg, 0.59 mmol), triethyl orthopropionate (208 mg, 237
1.18 mmol) and acetic acid (106 mg, 101
L, 1.77 mmol) in absolute ethanol (3 mL) at 110 ◦C for 24 h.
Yield: 114 mg (92%) as a light tan powder, m.p. 262–264 C; IR (nujol): 3169, 1681, 1627 cm−1; 1H-NMR
(400 MHz, DMSO-d6): 12.3 (br s, 1H), 8.01 (d, J = 2.5 Hz, 1H), 7.79 (dd, J = 8.7, 2.5 Hz, 1H), 7.62 (d, J =
(
10b).
This compound was prepared from
µL,
µ
◦
δ
8.7 Hz, 1H), 2.62 (q, J = 7.5 Hz, 2H), 1.24 (t, J = 7.5 Hz, 3H); 13C-NMR (101 MHz, DMSO-d6):
δ 160.8,
159.0, 147.7, 134.3, 130.1, 129.1, 124.7, 122.1, 27.8, 11.2; HRMS (ESI): m/z for C10H935ClN2O [M + 1]+:
calcd.: 209.0482; found: 209.0484.
6-Chloro-2-propylquinazolin-4(3H)-one
(
10c).
This compound was prepared from
L,
2-amino-5-chlorobenzamide (100 mg, 0.59 mmol), triethyl orthobutyrate (224 mg, 255
µ
1.18 mmol) and acetic acid (106 mg, 101 µ
L, 1.77 mmol) in absolute ethanol (3 mL) at 110 ◦C for 24 h.
Yield: 116 mg (88%) as a light tan powder, m.p. 252–254 ◦C (lit [33] m.p. 257–259 ◦C); IR (nujol): 3165,
1
1681, 1618 cm−1; H-NMR (400 MHz, CDCl3):
δ 12.4 (br s, 1H), 8.01 (d, J = 2.4 Hz, 1H), 7.80 (dd,
J = 8.7, 2.4 Hz, 1H), 7.62 (d, J = 8.7 Hz, 1H), 2.57 (t, J = 7.4 Hz, 2H), 1.74 (sextet, J = 7.4 Hz, 2H), 0.93 (t,
J = 7.4 Hz, 3H); 13C-NMR (101 MHz, DMSO-d6):
160.8, 158.0, 147.7, 134.4, 130.1, 129.1, 124.7, 122.1,
36.3, 20.1, 13.5; HRMS (ESI): m/z for C11H1135ClN2O [M + 1]+: calcd.: 223.0638; found: 223.0637.
δ
6-Chloro-2-phenylquinazolin-4(3H)-one 10d). This compound was prepared from
2-amino-5-chlorobenzamide (100 mg, 0.59 mmol), triethyl orthobenzoate (264 mg, 267 L,
1.18 mmol) and acetic acid (106 mg, 101
L, 1.77 mmol) in absolute ethanol (3 mL) at 110 ◦C for 24 h.
Yield: 147 mg (97%) as white crystals, m.p. 292–293 ◦C (lit [37] m.p. 295–296 ◦C); IR (nujol): 3151,
(
µ
µ