Synthesis of novel 1,2,3-triazole derivatives of 2,3-dihydroquinazolin-4(1H)-one
1
J = 15.2 Hz, 1H, CH ) ppm; C NMR (100 MHz,
3
(100 MHz, DMSO-d6): d = 162.9, 161.8 (d, JC-
= 241.2 Hz), 158.6, 146.9, 143.3, 138.5, 136.3, 134.2
2
b
DMSO-d ): d = 162.9, 158.6, 146.8, 143.4, 138.0, 135.4,
6
F
1
1
5
1
33.9, 133.4, 130.4, 129.2, 128.9, 128.1, 128.0, 127.9,
27.6, 126.7, 125.2, 117.6, 115.1, 115.0, 114.8, 69.9, 61.5,
2.5, 47.4 ppm; IR (KBr): mꢀ = 3278, 3064, 2928, 2854,
(d, JC-F = 134.5 Hz), 133.9, 133.3, 130.0, 129.9, 129.3,
129.1, 129.0, 128.1, 128.0, 125.6, 125.1, 117.7, 115.6 (d,
JC-F = 21.2 Hz), 115.1, 115.0, 70.1, 61.5, 53.3, 46.8,
21.4 ppm; IR (KBr): mꢀ = 3390, 3054, 2928, 2850, 1650,
-
1
636, 1527 cm
.
-
1
1590 cm .
3
-Benzyl-2-[4-[[1-(4-bromobenzyl)-1H-1,2,3-triazol-4-
yl]methoxy]phenyl]-2,3-dihydroquinazolin-4(1H)-one
8f, C H BrN O )
3-(4-Fluorobenzyl)-2-[4-[[1-(4-fluorobenzyl)-1H-1,2,3-tri-
azol-4-yl]methoxy]phenyl]-2,3-dihydroquinazolin-4(1H)-
one (8i, C H F N O )
(
3
1
26
5 2
1
Pale yellow solid; yield 0.46 g (80 %); m.p.: 94–97 °C; H
3
1 25 2 5 2
1
NMR (400 MHz, DMSO-d ): d = 8.28 (s, 1H, triazole),
Yellow solid; yield 0.37 g (70 %); m.p.: 68–70 °C; H
6
7
.69 (d, J = 8.0 Hz, 1H, H ), 7.58 (d, J = 8.4 Hz, 2H, Ar),
5
NMR (400 MHz, DMSO-d ): d = 8.27 (s, 1H, triazole),
6
7
.35–7.20 (m, 11 H, Ar, H , NH), 6.99 (d, J = 8.8 Hz, 2H,
7
7.69 (d, J = 8.0 Hz, 1H, H ), 7.41–7.38 (m, 2H, Ar), 7.31–
5
Ar), 6.69 (t, J = 8.0 Hz, 1H, H ), 6.64 (d, J = 8.0 Hz, 1H,
6
7.28 (m, 3H, Ar, H7), 7.24–7.19 (m, 5H, Ar, NH), 7.14 (t,
J = 8.8 Hz, 2H, Ar), 6.98 (d, J = 8.4 Hz, 2H, Ar), 6.69 (t,
J = 8.0 Hz, 1H, H ), 6.65 (d, J = 8.0 Hz, 1H, H ), 5.71 (d,
H ), 5.68 (d, J = 2.4 Hz, 1H, CH), 5.59 (s, 2H, CH ), 5.29
8 2
(
d, J = 15.6 Hz, 1H, CH ), 5.10 (s, 2H, CH ), 3.79 (d,
2a 2
6
8
1
J = 15.6 Hz, 1H, CH ) ppm; C NMR (100 MHz,
3
J = 2.0 Hz, 1H, CH), 5.59 (s, 2H, CH ), 5.19 (d,
2
2
b
DMSO-d ): d = 162.9, 158.6, 146.9, 143.4, 138.0, 135.8,
J = 15.2 Hz, 1H, CH ), 5.09 (s, 2H, CH ), 3.85 (d,
2
6
2a
1
3
1
1
5
1
33.9, 133.4, 132.2, 130.7, 128.9, 128.1, 127.9, 127.9,
27.6, 125.2, 121.9, 121.9, 117.6, 115.1, 115.0, 69.4, 61.5,
2.5, 47.4 ppm; IR (KBr): mꢀ = 3315, 3054, 2933, 2854,
J = 15.2 Hz, 1H, CH ) ppm; C NMR (100 MHz,
2b
DMSO-d ): d = 163.3 (d, J
= 229.2 Hz), 162.9, 160.9
C-F
6
(d, JC-F = 222.0 Hz), 158.6, 146.9, 143.4, 134.3 (d, JC-
-
1
640, 1520 cm
.
= 116.6 Hz), 133.9, 133.3, 132.7 (d, JC-F = 12.0 Hz),
F
1
30.8, 130.7, 129.9 (d, JC-F = 32.4 Hz), 128.1, 128.0,
25.0, 117.7, 116.1 (d, JC-F = 86.4 Hz), 115.6 (d, JC-
3
-(4-Fluorobenzyl)-2-[4-[[1-(2-methylbenzyl)-1H-1,2,3-
1
triazol-4-yl]methoxy]phenyl]-2,3-dihydroquinazolin-
(1H)-one (8 g, C H FN O )
=
84.4 Hz), 115.0, 114.9, 70.0, 61.5, 52.5, 46.8 ppm; IR
-1
F
4
3
2
28
5
2
KBr): mꢀ = 3290, 3055, 2928, 2842, 1652, 1597 cm
( .
1
Cream solid; yield 0.40 g (75 %); m.p.: 63–64 °C;
H
NMR (400 MHz, DMSO-d ): d = 8.17 (s, 1H, triazole),
2-[4-[[1-(2,4-Dichlorobenzyl)-1H-1,2,3-triazol-4-yl]methoxy]-
phenyl]-3-(4-fluorobenzyl)-2,3-dihydroquinazolin-4(1H)-one
(8j, C H Cl FN O )
6
7
.68 (d, J = 6.8 Hz, 1H, H ), 7.31–7.21 (m, 8H, Ar, H ,
5 7
NH), 7.17–7.06 (m, 4H, Ar), 6.98 (d, J = 8.4 Hz, 2H, Ar),
31
24
2
5 2
1
6
5
.70–6.63 (m, 2H, H , H ), 5.70 (d, J = 2.0 Hz, 1H, CH),
6
Yellow solid; yield 0.47 g (80 %); m.p.: 97–99 °C; H
8
.61 (s, 2H, CH ), 5.18 (d, J = 15.5 Hz, 1H, CH ), 5.09
2 2a
NMR (400 MHz, DMSO-d ): d = 8.26 (s, 1H, triazole),
6
(
s, 2H, CH ), 3.84 (d, J = 15.5 Hz, 1H, CH ), 2.29 (s, 3H,
2
7.70 (dd, J = 7.5, 1.5 Hz, 1H, H ), 7.68 (dd, J = 2.0 Hz,
5
2b
1
3
Me) ppm; C NMR (100 MHz, DMSO-d ): d = 162.9,
1H, Ar), 7.48 (dd, J = 8.4, 2.0 Hz, 1H, Ar), 7.31–7.27 (m,
6
1
61.5 (d, JC-F = 240.0 Hz), 158.6, 147.1, 143.3, 138.3,
4H, Ar, H ), 7.24–7.20 (m, 2H, Ar), 7.14 (t, J = 8.8 Hz,
7
1
36.8, 133.9 (d, JC-F = 136.2 Hz), 133.3, 130.9, 129.9 (d,
2H, Ar), 6.99 (d, J = 8.8 Hz, 2H, Ar), 6.68 (td, J = 7.5,
1.2 Hz, 1H, H ), 6.64 (d, J = 7.5 Hz, 1H, H ), 5.71 (dd,
JC-F = 8.1 Hz), 129.6, 129.3, 129.1, 128.8, 128.2, 128.0
6
8
(
d, JC-F = 8.4 Hz), 125.5, 125.2, 117.7, 115.6 (d, JC-
J = 2.4 Hz, 1H, CH), 5.70 (s, 2H, CH ), 5.19 (d,
2
=
21.3 Hz), 115.1, 115.0, 70.0, 61.5, 51.4, 46.1,
J = 15.2 Hz, 1H, CH ), 5.11 (s, 2H, CH ), 3.84 (d,
2a
F
2
1
3
1
9.1 ppm; IR (KBr): mꢀ = 3391, 3056, 2924, 2846, 1658,
613, 1590 cm
J = 15.2 Hz, 1H, CH ) ppm; C NMR (100 MHz,
2b
-
1
1
.
DMSO-d6): d = 162.9, 161.8 (d, JC-F = 241.1 Hz),
1
58.6, 146.9, 143.2, 134.5, 134.2 (d, JC-F = 2.9 Hz),
3
-(4-Fluorobenzyl)-2-[4-[[1-(3-methylbenzyl)-1H-1,2,3-
1
34.2, 133.9, 133.3, 132.8, 132.4, 129.9 (d, JC-
triazol-4-yl]methoxy]phenyl]-2,3-dihydroquinazolin-
(1H)-one (8 h, C H FN O )
=
8.1 Hz), 129.6, 128.4, 128.1, 128.0, 125.6, 117.7,
F
4
3
2
28
5 2
115.6 (d, JC-F = 21.2 Hz), 115.1, 115.0, 114.8, 70.0, 61.4,
1
Deep yellow oil; yield 0.40 g (75 %); H NMR (400 MHz,
5
0.5, 46.8 ppm; IR (KBr): mꢀ = 3311, 3044, 2912, 2850,
DMSO-d ): d = 8.26 (s, 1H, triazole), 7.70 (dd, J = 7.7,
6
-1
1
634, 1516 cm
.
1
.2 Hz, 1H, H ), 7.31–7.20 (m, 6H, Ar, NH, H ), 7.16–7.10
5 7
(
m, 6H, Ar), 6.98 (d, J = 8.4 Hz, 2H, Ar), 6.69 (td,
Acknowledgments We gratefully acknowledge the partial financial
support from Tehran University of Medical Sciences Research
Council and International Campus (TUMS-IC) with project No.
J = 7.7, 0.8 Hz, 1H, H ), 6.65 (d, J = 7.7 Hz, 1H, H ),
6
8
5
.71 (d, J = 2.0 Hz, 1H, CH), 5.55 (s, 2H, CH ), 5.19 (d,
2
9
3-02-169-25050.
J = 15.2 Hz, 1H, CH ), 5.10 (s, 2H, CH ), 3.85 (d,
2
1
J = 15.2 Hz, 1H, CH ), 2.28 (s, 3H, Me) ppm; C NMR
a
2
3
2
b
123