ŞENOL et al./Turk J Chem
CDCl3 -d1): δ 160.6, 159.7, 148.2, 148.0, 135.0, 130.7, 129.1, 127.8, 127.7, 126.8, 122.4, 114.8, 55.9. HRMS
+
(ESI): m/z [M+H] calcd. for C15 H13 N2 O2 : 253.0972; found: m/z 253.0981.
2-Methyl-3(2-methylpropyl)quinazolin-4(3H )-one (4d)
1
Orange solid (44 mg, 81%); mp: 71–73 °C. FTIR υmax (KBr): 2963, 2870, 1669, 1594, 1473 cm−1
.
H NMR
(400 MHz, DMSO-d6): δ 8.07 (dd, J = 7.8 Hz, 2 Hz, 1H), 7.79–7.74 (m, 1H), 7.56 (d, J = 7.6 Hz, 1H),
7.48–7.44 (m, 1H), 3.91 (d, J = 7.2 Hz, 2H), 2.58 (s, 3H), 2.10 (t, J = 6.8 Hz, 1H), 0.88 (d, J = 6.8 Hz, 6H).
13
C NMR (100 MHz, DMSO-d6): δ 162.3, 154.6, 147.0, 134.2, 126.9, 126.4, 126.3, 120.4, 51.1, 28.1, 23.5, 20.1.
+
HRMS (ESI): m/z [M+H] calcd. for C13 H17 N2 O: 217.1335; found: m/z 217.1334.
4.4. General method for synthesis of 2-substituted 2,3-dihydroquinazolin-4(1H )-ones (6a–6g)
N -(2-Aminobenzoyl)benzotriazoles (0.2 mmol) 1 were reacted with aldehydes (0.3 mmol) 5 and ammonium
acetate (0.3 mmol) under solvent-free conditions. After completion of the reaction, the mixture was washed
with water. The desired product was recrystallized from ethyl alcohol. (54%–95%).
2-Phenyl-2,3-dihydro quinazolin-4(1H )-one (6a)
White solid (34 mg, 76%, lit. [72] 95%); mp: 235–236 °C (lit. [72] 225–227 °C). FTIR υmax (KBr): 3309, 1655,
1
1512 cm−1 . H NMR (400 MHz, DMSO-d6): δ 8.27 (s, 1H), 7.58 (d, J = 8 Hz, 1H), 7.47 (d, J = 7.2 Hz, 2H),
7.38–7.32 (m, 3H), 7.21 (t, J = 7.6 Hz, 1H), 7.09 (s, 1H), 6.72 (d, J = 8 Hz, 1H), 6.64 (t, J = 7.4 Hz, 1H),
13
5.73 (s, 1H). C NMR (100 MHz, DMSO-d6): δ 164.0, 148.3, 142.0, 133.7, 128.9, 128.8, 127.8, 127.3, 117.5,
+
115.4, 114.8, 67.0. HRMS (ESI): m/z [M+H] calcd. for C14 H13 N2 O: 225.1022; found: m/z 225.1020.
7-Chloro-2-ethyl-2,3-dihydroquinazolin-4(1H )-one (6b)
White solid (32 mg, 72%, lit. [73] 30%); mp: 133–134 °C (lit. [73] 130–132 °C). FTIR υmax (KBr): 3363, 3218,
1
2968, 1645, 1476, 779 cm−1
.
H NMR (400 MHz, DMSO-d6): δ 7.77 (d, J = 8 Hz, 1H), 6.68 (d, J = 8 Hz,
1H), 6.65 (s, 1H), 6.57 (br s, 1H), 4.83 (t, J = 5.6 Hz, 1H), 4.34 (br s, 1H), 1.82–1.72 (m, 2H), 1.02 (t, J =
13
3 Hz, 3H). C NMR (100 MHz, DMSO-d6): δ 164.6, 148.1, 139.7, 130.0, 119.5, 114.3, 114.1, 66.4, 28.6, 8.2.
+
HRMS (ESI): m/z [M+H] calcd. for C10 H12 N2 O35 Cl: 211.0633; found: m/z 211.0636.
2-(2-Furanyl)-7-methyl-2,3-dihydroquinazolin-4(1H )-one (6c)
1
Pale yellow solid (43 mg, 95%); mp: 187–188 °C. FTIR υmax (KBr): 3300, 3185, 1647, 1489, 1014 cm−1
.
H
NMR (400 MHz, DMSO-d6): δ 7.77 (d, J = 7.6 Hz, 1H), 7.38 (s, 1H), 6.68 (d, J = 8 Hz, 1H), 6.48 (s,
13
1H), 6.40 (d, J = 3.2 Hz, 1H), 6.35 (s, 1H), 6.32 (s, 1H), 5.87 (s, 1H), 2.27 (s, 3H). C NMR (100 MHz,
DMSO-d6): δ 164.6, 152.2, 146.1, 145.0, 143.1, 128.5, 121.2, 115.2, 113.3, 110.5, 108.2, 62.0, 21.8. HRMS
+
(ESI): m/z [M+H] calcd. for C13 H13 N2 O2 : 229.0972, found: m/z 229.0964.
6-Bromo-(2-thiophenyl)-2,3-dihydro quinazolin-4(1H )-one (6d)
1
White solid (33 mg, 54%), mp: 229–230 °C. FTIR υmax (KBr): 3305, 1654, 1482, 819 cm−1
.
H NMR (400
MHz, DMSO-d6): δ 8.63 (s, 1H), 7.63 (d, J = 2 Hz, 1H), 7.50 (s, 1H), 7.44 (d, J = 5.2 Hz, 1H), 7.38 (dd,
J = 8.4 Hz, J = 2.8 Hz, 1H), 7.09 (d, J = 3.6 Hz, 1H), 6.96–6.94 (m, 1H), 6.71 (d, J = 8.4 Hz, 1H), 6.02
13
(s, 1H). C NMR (100 MHz, DMSO-d6): δ 162.3, 146.7, 146.4, 136.3, 129.7, 127.0, 126.6, 126.3, 117.5, 117.1,
+
108.8, 62.7. HRMS (ESI): m/z [M+H] calcd. for C12 H10 N2 OS79 Br: 308.9692; found: m/z 308.9692.
1589