682
M. M. HERAVI, F. DERIKVAND, AND L. RANJBAR
6
,6-Dimethyl-9(4-methoxy-phenyl)-5,6,7,9-tetrahydro-4H-1,2,4-triazolo
ꢀ
[
1
5,1-b]quinazolin-8-one. Mp 222–224 C; IR (KBr): n
¼ 2600–3300, 1652,
3
max
ꢁ
1
1
576 cm ; H NMR (DMSO, 300 MHz): d ¼ 0.98 (s, 3H, CH ). 1.05 (s, 3H,
H
0
CH ). 2.06 (d, J ¼ 16.2 Hz, 1H, H-5), 2.22 (d, J ¼ 16.2 Hz, 1H, H-5 ), 2.49–2.53
3
(
(
m, 2H, H-7), 3.70 (s, 3H, OCH ), 6.16 (s, 1H, H-9), 6.95–7.5 (m, 4H, Ar-H), 7.67
3
s, 1H, H-2), 11.10 (s, 1H, NH) ppm.
6
,6-Dimethyl-9-(4-hydroxy-phenyl)-5,6,7,9-tetrahydro-1,2,4-triazolo-
ꢀ
[
1
5,1-b]quinazolin-8(4H)-one. Mp > 300 C; IR (KBr): n
586, 1516, 1476, 1414 cm
¼ 2650–3207, 1650,
H
max
ꢁ
1
1
;
H NMR (DMSO, 300 MHz): d ¼ 0.97 (s, 3H,
CH ). 1.04 (s, 3H, CH ). 2.04 (d, J ¼ 16.08 Hz, 1H, H-5), 2.19 (d, J ¼ 16.2 Hz, 1H,
3
0
3
H-5 ), 2.50–2.59 (m, 2H, H-7), 6.10 (s, 1H, H-9), 6.64 (d, J ¼ 7.91 Hz, 2H, Ar-H),
6
NH) ppm. Anal. calcd. (%): C, 65.81; H, 5.81; N, 18.06; C H N O , Found (%):
.99 (d, J ¼ 7.91 Hz, 2H, Ar-H), 7.66 (s, 1H, H-2), 9.41 (s, 1H, OH), 11.05 (s, 1H,
1
7
18
4
2
C, 65.32; H, 5.73; N, 17.89.
6
,6-Dimethyl-9-(4-nitro-phenyl)-5,6,7,9-tetrahydro-4H-1,2,4-triazolo-
ꢀ
[
1
3
(
5,1-b]quinazolin-8-one. Mp 307–309 C; IR (KBr): n
¼ 2600–3448, 1646,
3
max
ꢁ
1 1
578, 1352, cm ; H NMR (DMSO, 300 MHz): d ¼ 0.95 (s, 3H, CH ). 1.03 (s,
H
0
H, CH ). 2.05 (d, J ¼ 16.23 Hz, 1H, H-5), 2.19 (d, J ¼ 16.23 Hz, 1H, H-5 ), 2.49
3
d, 2H, J ¼ 16.2, H-7), 6.37 (s, 1H, H-9), 7.48 (d, J ¼ 8.4 Hz, 2H, Ar-H), 8.15 (d,
J ¼ 8.4 Hz, 2H, Ar-H), 7.73 (s, 1H, H-2), 11.31 (s, 1H, NH) ppm. Anal. calcd.
%): C, 60.18; H, 5.015; N, 20.65; C H N O . Found: C, 60.18; H,5.478; N, 20.62.
(
1
7
17
5
3
6
,6-Dimethyl-9(3-nitro-phenyl)-5,6,7,9-tetrahydro-1,2,4-triazolo[5,1-b]
ꢀ
quinazolin-8(4H)-one. Mp ¼ 266–269 C; IR (KBr): n
¼ 2600–3450, 1646, 1580,
H
max
ꢁ
1 1
352, 1550, 1527, 1482, 1415 cm ; H NMR (DMSO, 300 MHz): d ¼ 0.98 (s, 3H,
3 3
1
CH ). 1.05 (s, 3H, CH ). 2.07–2.57 (m, 4H, H-5 & H-7), 6.42 (s, 1H, H-9), 7.58–7.68
(
m, 2H, Ar-H), 7.74 (s, 1H, H-2), 8.06 (s, 1H, Ar-H), 8.11 (d, J ¼ 13.15, 1H, Ar-H),
1
Found: C, 59.97; H, 4.76; N, 20.52.
1.32 (s, 1H, NH) ppm. Anal. calcd. (%): C, 60.18; H, 5.015; N, 20.65, C H N O .
17 17 5 3
6
,6-Dimethyl-9(2-naphthyl)-5,6,7,9-tetrahydro-1,2,4-triazolo[5,1-b]
ꢀ
quinazolin-8(4H)-one. Mp: 287–290 C; IR (KBr) nmax ¼ 2926–3449, 1650,
ꢁ
1
1
1
577 cm ; H NMR (DMSO, 300 MHz) d ¼ 0.97 (s, 3H, CH ). 1.05 (s, 3H,
3 2 2
H
3
CH ). 2.03 (d, J ¼ 16.14 Hz, 1H, CH ), 2.20 (d, J ¼ 16.26 Hz, 1H, CH ), 2.50 (m,
2
H, CH ), 6.38 (s, 1H, CH), 7.25–7.91 (m, 7H, H ), 7.69 (s, 1H, CH), 11.21 (s,
2 Ar
1H, NH) ppm. Anal. calcd. (%): C, 73.25; H, 5.81; N, 16.28, C H N O. Found:
21 20 4
C, 71.73; H, 5.91; N, 15.91.
3
,3-Dimethyl-12-phenyl-1,2,3,4,5,12-hexahydrobenzo[4,5]imidazo[2,1-b]-
ꢀ
quinazolin-1-one. Mp > 300 C; IR (KBr): n
¼ 3445, 2885, 1640, 1618, 1610,
max
ꢁ
1
1
1
565 cm ; H NMR (DMSO, 300 MHz): d ¼ 0.92 (s, 3H, CH ), 1.05 (s, 3H,
H
3
0
CH ), 2.04 (d, J ¼ 16.14 Hz, 1H, H-4), 2.25 (d, J ¼ 15.66 Hz, 1H, H-4 ), 2.64 (br s,
3
2
H, H-2), 6.41 (s, 1H, H-12), 6.93–7.38 (m, 9H, Ar-H), 11.12 (s, 1H, NH) ppm.
1
2(4-Chlorophenyl)-3,3-dimethyl-1,2,3,4,5,12-hexahydrobenzo[4,5] imi-
ꢀ
dazo[2,1-b]quinazolin-1-one. Mp > 300 C; IR (KBr): n
613, 1590, 1566 cm ; H NMR (DMSO, 300 MHz): d ¼ 0.96 (s, 3H, CH ), 1.06
¼ 3485, 3045, 1645,
3
max
ꢁ
1 1
1
H