NMR (CDCl3, 400 MHz): δ 8.46 (d, J = 2.7 Hz, 1H), 7.95 (dd, J
= 8.1, 1.6 Hz, 1H), 7.76 (s, 1H), 7.76-7.72 (m, 2H), 7.43-7.33 (m,
1H), 6.99-6.89 (m, 2H), 6.70 (d, J = 8.6 Hz, 1H), 6.58 (ddd, J =
7.2, 6.6, 0.9 Hz, 1H), 3.85 (d, J = 3.0 Hz, 3H), 3.24-3.15 (m, 2H),
1.69 (dd, J = 10.0, 4.9 Hz, 2H), 1.50-1.38 (m, 2H), 1.30 (dd, J =
11.0, 7.1 Hz, 8H), 0.9-0.84 (m, 3H); 13C NMR (CDCl3, 100
MHz): δ 166.2, 162.3, 155.6, 151.8, 135.0, 131.0, 130.0, 122.7,
114.3, 114.0, 111.3, 107.3, 99.9, 55.4, 42.8, 31.8, 29.4, 29.2, 29.4,
27.2, 22.6, 14.1; HRMS(ESI) calculated for C23H30N2O3 [M+H]+:
383.2335, found: 383.2334.
(m, 2H), 7.04-6.88 (m, 2H), 6.71 (d, J = 8.5 Hz, 1H), 6.61-6.53
(m, 1H), 3.89 (s, 3H), 3.20 (td, J = 6.9, 5.1 Hz, 2H), 1.68 (dd, J =
14.9, 7.1 Hz, 2H), 1.51-1.39 (m, 2H), 1.31 (ddd, J = 10.4, 7.9, 3.6
Hz, 8H), 0.89 (dd, J = 9.3, 4.5 Hz, 3H); 13C NMR (CDCl3, 100
MHz): δ 166.4, 158.5, 152.2, 152.0, 135.1, 133.1, 131.2, 127.7,
121.0, 118.9, 114.1, 111.4, 111.2, 107.4, 55.7, 43.0, 32.0, 29.5,
29.3, 29.2, 27.3, 22.8, 14.2; HRMS(ESI) calculated for
C23H30N3O3 [M+H]+: 383.2335, found: 383.2331.
4.1.14 2-(2-chlorophenyl)-3-hydroxy-1-octyl-2,3-dihydroquina
1
zolin-4(1H)-one (5j): White solid, 90% yield. mp: 53-55 ℃. H
4.1.9 3-hydroxy-1-octyl-2-(p-tolyl)-2,3-dihydroquinazolin-4(1H)
-one (5e): White solid, 78% yield. mp: 60-61 ℃. 1H NMR
(CDCl3, 400 MHz): δ 8.50 (s, 1H), 7.96 (dd, J = 8.1, 1.6 Hz, 1H),
7.76 (s, 1H), 7.69 (d, J = 8.1 Hz, 2H), 7.39 (ddd, J = 8.6, 7.1, 1.6
Hz, 1H), 7.24 (s, 1H), 6.71 (d, J = 8.6 Hz, 1H), 6.59 (ddd, J = 8.0,
7.2, 0.9 Hz, 1H), 3.20 (dd, J = 11.7, 6.8 Hz, 2H), 2.40 (s, 3H),
1.68 (dd, J = 14.8, 7.1 Hz, 2H), 1.49-1.39 (m, 2H), 1.38-1.21 (m,
9H), 0.88 (t, J = 6.9 Hz, 3H); 13C NMR (CDCl3, 100 MHz): δ
166.3, 156.1, 152.0142.2, 135.2, 131.1, 129.7, 128.4, 127.6,
114.1, 111.5, 107.3, 43.0, 32.0, 29.5, 29.3, 29.2, 27.3, 22.8, 21.7,
14.2; HRMS(ESI) calculated for C23H30N2O2 [M+H]+: 367.2386,
found: 367.2380.
NMR (CDCl3, 400 MHz): δ 8.97 (s, 1H), 8.17 (dd, J = 7.7, 1.4
Hz, 1H), 7.98 (dd, J = 8.1, 1.6 Hz, 1H), 7.74 (t, J = 4.4 Hz, 1H),
7.46-7.37 (m, 3H), 7.36 -7.30 (m, 1H), 6.72 (d, J = 8.6 Hz, 1H),
6.65-6.58 (m, 1H), 3.20 (dd, J = 11.8, 6.9 Hz, 2H), 1.68 (dd, J =
14.9, 7.1 Hz, 2H), 1.49-1.40 (m, 2H), 1.37-1.24 (m, 8H), 0.88 (t,
J = 6.9 Hz, 3H); 13C NMR (CDCl3, 100 MHz): δ 166.1, 153.0,
152.1, 135.4, 135.1, 132.6, 131.2, 130.1, 128.4, 127.3, 114.2,
111.5, 107.0, 43.0, 32.0, 29.5, 29.3, 29.2, 28.3, 22.8, 14.2;
HRMS(ESI) calculated for C22H27ClN2O2 [M+H]+: 387.1839,
found: 387.1835.
4.1.15 1-hexadecyl-3-hydroxy-2-(2-hydroxyphenyl)-2,3-dihydro
quinazolin-4(1H)-one (5k): White solid, 84% yield. mp: 67-69 ℃.
1H NMR (CDCl3, 400 MHz): δ 8.59 (s, 1H), 7.94 (dd, J = 8.1, 1.6
Hz, 1H), 7.66 (s, 1H), 7.39 (ddd, J = 8.9, 6.1, 1.6 Hz, 2H), 7.08
(d, J = 8.2 Hz, 1H), 6.99- 6.95 (m, 1H), 6.73 (d, J = 8.5 Hz, 1H),
6.60 (t, J = 7.5 Hz, 1H), 3.22 (dd, J = 11.1, 6.2 Hz, 2H), 1.72-
1.68 (m, 2H), 1.44 (dd, J = 10.7, 4.9 Hz, 2H), 1.26 (d, J = 10.3
Hz, 26H), 0.88 (s, 3H); 13C NMR (CDCl3, 100 MHz): δ 164.9,
158.5, 157.2, 152.0, 135.4, 134.7, 133.0, 132.5, 131.9, 131.0,
119.7, 117.5, 115.2, 114.3, 114.2, 111.5, 111.3, 106.6, 42.9, 31.9,
29.7-29.1, 27.2, 22.7, 14.1; HRMS(ESI) calculated for
C30H44N2O3 [M+H]+: 481.4522, found: 481.4518.
4.1.10 2-(4-chlorophenyl)-3-hydroxy-1-octyl-2,3-dihydroquin
azolin-4(1H)-one (5f): White solid, 80% yield. mp: 53-54 ℃. 1H
NMR (CDCl3, 400 MHz): δ 8.30 (s, 1H), 8.00 (dd, J = 8.1, 1.6
Hz, 1H), 7.75 (s, 1H), 7.69 (d, J = 8.1 Hz, 2H), 7.41 (ddd, J = 8.6,
7.1, 1.6 Hz, 1H), 7.24 (s, 1H), 6.71 (d, J = 8.6 Hz, 1H), 6.59 (ddd,
J = 8.0, 7.2, 0.9 Hz, 1H), 3.20 (dd, J = 11.7, 6.8 Hz, 2H), 1.68
(dd, J = 14.8, 7.1 Hz, 2H), 1.49-1.39 (m, 2H), 1.38-1.21 (m, 9H),
0.89 (t, J = 6.9 Hz, 3H); 13C NMR (CDCl3, 100 MHz): δ 166.1,
154.9, 152.1, 137.8, 135.4, 131.1, 129.6, 129.4, 129.0, 114.2,
111.6, 107.0, 43.0, 32.0, 29.5, 29.3, 29.2, 27.3, 22.8, 14.2;
HRMS(ESI) calculated for C22H27ClN2O2 [M+H]+: 387.1839,
found: 387.1835.
4.1.16 3-hydroxy-2-(2-hydroxyphenyl)-1-tetradecyl-2,3-dihydro
quinazolin-4(1H)-one (5l): Yellow solid, 83% yield. mp: 71-
72 ℃. 1H NMR (CDCl3, 400 MHz): δ 8.58 (s, 1H), 7.95 (dd, J =
8.2, 1.7 Hz, 1H), 7.68 (d, J = 4.9 Hz, 1H), 7.50-7.34 (m, 2H),
7.34-7.22 (m, 1H), 7.08 (dd, J = 4.9, 4.5 Hz, 1H), 7.02-6.90 (m,
1H), 6.72 (d, J = 9.0 Hz, 1H), 6.60 (ddd, J = 8.1, 4.6, 1.0 Hz, 1H),
3.30-3.15 (m, 2H), 2.05 (s, 1H), 1.71 (dd, J = 15.2, 7.5 Hz, 2H),
1.43 (dd, J = 15.5, 7.3 Hz, 3H), 1.27 (d, J = 9.9 Hz, 19H), 0.88
(dd, J = 8.2, 7.1 Hz, 3H; 13C NMR (CDCl3, 100 MHz): δ 165.0,
158.5, 157.2, 152.1, 135.5, 133.1, 132.0, 131.1, 119.8, 117.5,
115.3, 114.3, 111.6, 106.6, 43.0, 32.1, 29.8-29.2, 27.3, 22.8, 14.3;
HRMS(ESI) calculated for C28H40N2O3 [M+H]+: 453.3535, found:
453.3534.
4.1.11 3-hydroxy-2-(4-hydroxyphenyl)-1-octyl-2,3-dihydroquina
1
zolin-4(1H)-one (5g): White solid, 87% yield. mp: 62-64 ℃. H
NMR (CDCl3, 400 MHz): δ 8.45 (d, J = 1.3 Hz, 1H), 7.95 (dt, J =
8.1, 1.5 Hz, 1H), 7.71 (s, 1H), 7.61 (dd, J = 8.6, 1.4 Hz, 2H), 7.39
(ddd, J = 7.1, 6.4, 1.6 Hz, 1H), 6.92-6.86 (m, 2H), 6.71 (d, J =
8.7 Hz, 1H), 6.59 (ddd, J = 8.2, 2.3, 1.1 Hz, 1H), 3.19 (s, 2H),
1.73-1.62 (m, 2H), 1.48-1.37 (m, 2H), 1.36-1.20 (m, 8H), 0.87
(dt, J = 7.1, 3.8 Hz, 3H); 13C NMR (CDCl3, 100 MHz): δ 167.0,
159.4, 156.1, 152.0, 135.4, 131.2, 130.4, 122.4, 116.2, 114.3,
111.6, 107.2, 43.0, 31.9, 29.5, 29.3, 29.2, 27.3, 22.8, 14.2;
HRMS(ESI) calculated for C22H28N2O3 [M+H]+: 369.2178, found:
369.2173.
4.1.17
1-dodecyl-3-hydroxy-2-(2-hydroxyphenyl)-2,3-dihydro
quinazolin-4(1H)-one (5m): Yellow solid, 78% yield. mp: 69-
71 ℃. 1H NMR (CDCl3, 400 MHz): δ 8.59 (s, 1H), 7.95 (dd, J =
8.4, 1.8 Hz, 1H), 7.76- 7.63 (m, 1H), 7.57- 7.34 (m, 2H), 7.34-
7.17 (m, 1H), 7.08 (d, J = 8.6 Hz, 1H), 7.03-6.91 (m, 1H), 6.73 (d,
J = 8.9 Hz, 1H), 6.60 (td, J = 8.1, 0.9 Hz, 1H), 3.21 (dd, J = 12.9,
7.5 Hz, 2H), 2.05 (d, J = 0.9 Hz, 1H), 2.01- 1.64 (m, 3H), 1.45
(dd, J = 14.7, 7.5 Hz, 3H), 1.39-0.93 (m, 14H), 0.88 (dd, J = 7.7,
7.0 Hz, 3H); 13C NMR (CDCl3, 100 MHz): δ 165.0, 158.5, 157.2,
152.1, 135.5, 133.1, 132.0, 131.1, 119.8, 117.5, 115.3, 114.3,
111.6, 106.6, 100.0, 43.0, 32.0, 29.8 - 29.5, 29.2, 27.3, 22.8, 21.2,
14.3; HRMS(ESI) calculated for C26H36N2O3 [M+H]+: 425.4334,
found: 425.4330.
4.1.12 3-hydroxy-2-(2-hydroxyphenyl)-1-octyl-2,3-dihydroquina
1
zolin-4(1H)-one (5h): White solid, 80% yield. mp: 73-75 ℃. H
NMR (CDCl3, 400 MHz):δ 10.08 (s, 1H), 8.58 (s, 1H), 7.95 (dd,
J = 8.1, 1.5 Hz, 1H), 7.67 (t, J = 4.5 Hz, 1H), 7.40 (qd, J = 7.2,
1.6 Hz, 2H), 7.28 (dd, J = 7.7, 1.6 Hz, 1H), 7.08 (d, J = 8.2 Hz,
1H), 6.96 (td, J = 7.5, 0.8 Hz, 1H), 6.72 (d, J = 8.5 Hz, 1H), 6.63-
6.58 (m, 1H), 3.21 (dd, J = 12.1, 7.0 Hz, 2H), 1.74-1.65 (m,
2H),1.50-1.40 (m, 2H), 1.36-1.26 (m, 8H), 0.89 (t, J = 6.8 Hz,
3H); 13C NMR (CDCl3, 100 MHz): δ 165.0, 158.5, 157.2, 152.1,
135.5, 133.1, 132.0, 131.1, 119.8, 117.5, 115.3, 114.3, 111.6,
106.6, 43.0, 32.0, 29.5, 29.3 29.2, 27.3, 22.8, 14.3; HRMS(ESI)
calculated for C22H28N2O3 [M+H]+: 369.3564, found: 369.3560.
4.1.18
1-decyl-3-hydroxy-2-(2-hydroxyphenyl)-2,3-dihydro
quinazolin-4(1H)-one (5n): White solid, 89% yield. mp:70-71 ℃.
1H NMR (CDCl3, 400 MHz): δ 8.59 (s, 1H), 7.95 (dd, J = 8.4, 1.8
Hz, 1H), 7.68 (d, J = 5.4 Hz, 1H), 7.57-7.35 (m, 2H), 7.32-7.22
(m, 1H), 7.08 (d, J = 8.6 Hz, 1H), 7.01-6.86 (m, 1H), 6.73 (d, J =
4.1.13 3-hydroxy-2-(2-methoxyphenyl)-1-octyl-2,3-dihydroquina
zolin-4(1H)-one (5i): White solid, 78% yield. mp: 52-54 ℃. H
NMR (CDCl3, 400 MHz): δ 8.95 (s, 1H), 8.07 (dd, J = 7.7, 1.7
Hz, 1H), 7.98 (dd, J = 8.1, 1.6 Hz, 1H), 7.78 (s, 1H), 7.50-7.34
1