B. Narayana et al. / European Journal of Medicinal Chemistry 41 (2006) 417–422
421
(
t, 1H, Ar–H), δ 7.30 (t, 1H, Ar–H), δ 7.37–7.44 (m, 4H, Ar–
7.05 (d (J = 8.4), 1H, Ar–H), δ 7.13 (dd (J = 10.8) 2H, Ar–H),
H), δ 7.49 (m 1H, Ar–H), δ 7.59 (t, 1H, Ar–H), δ 8.72 (s, 2H,
δ 7.45 (m 2H, Ar–H), δ 7.52 (dd (J = 6.6) 2H, Ar–H), δ 7.59
,
,
Ar–H)
(t, 1H, Ar–H)
1
3
2
13
2
C-NMR: (CdCl , 125 MHz): 46.32, 116.29 (d, J
C-NMR: (CdCl , 75 MHz) 46.40, 116.23 (d, JC–F
3
C–F
3
2
=
21.25), 122.19, 124.90, 125.92, 126.86, 126.95, 129.60,
= 22.5), 116.38 (d, JC–F = 22.5), 116.38, 116.53, 122.45,
124.84, 125.99, 126.96, 127.11, 129.46, 130.51, 130.63,
130.84, 131.32, 131.96, 132.80, 132.91, 133.78, 154.69(d,
1
1
30.84, 131.55, 131.94, 132.96, 133.03, 134.00,134.31,
50.70, 151.33, 157.59, 160.4(d, J
1
= 248.8), 165.40
C–F
+
1
MS: m/z 389(M , 90%), m/z 360(100%, (M – 1)–N ), m/z
JC–F = 298.5), 165.43, 165.58; DEPT: 46.4(–ve), 116.08,
2
3
40(23%, C H ClFN ) m/z 326 (10.2%, C H ClFN )
116.23, 116.38, 116.53,124.79,125.97,129.43, 130.51,
130.63, 130.81, 131.30, 132.80, 132.90
1
9
15
3
19 16
2
Anal. calc. for C H ClFN ; N, 17.97 Found: N, 17.95.
2
1
13
5
+
GCMS: m/z 406 (M , 26%), m/z 404(M-2, 26%) m/z 370
6
.2. 8-Chloro-6-(2-fluorophenyl)-1-(4-nitro-1H-indol-2-yl)-4H-
(M–F , 25%), m/z 354, (C H ClFN , 100%)
2
20 17
3
[
1,2,4]triazolo[4,3-a][1,4]benzodiazepine
Anal. calc. for C H ClF N ; N, 13.77 Found: N, 13.75.
21 13 2 4
–
1
–1
FT-IR: (KBr): 3041.5 cm and 2964.1 cm (–CHstr),
6.5. 1-(2-Bromo-5-methoxyphenyl)-8-chloro-6-(2-
fluorophenyl)-4H-[1,2,4]triazolo [4,3-a] [1,4] benzodiazepine
–1
–1
–1
1
(
614.3 cm (–C = N), 1481.2 cm (–CH ), 1097.4 cm
2
–
1
Ar–F), 1026.1 cm (Ar–Cl).
1
–1
–1
H-NMR: (CdCl ): δ 4.2 (d (J = 10.4) 1H, –CH ), δ 5.61 (d
J = 10.4) 1H, –CH ), δ 6.64(s, 1H, Ar–H), δ 7.07 (t, 1H, Ar–
H), δ 7.23–7.31 (m, 3H, Ar–H), δ 7.41(s 1H, Ar–H), δ 7.49–
.52 (m, 3H, Ar–H), δ 7.76 (t, 1H, Ar–H), δ 7.92 (d (J = 6.2)
H, Ar–H), δ 8.24 (d (J = 6.37) 1H, Ar–H), δ 10.77 (s, 1H,
NH)
C-NMR: (CdCl , 125 MHz): 46.21, 116.35(d, J
21.12), 120.22, 121.14, 124.80, 125.86, 125.93, 126.69,
FT-IR (KBr): 3055.0 cm and 2926 cm (–CH ), 1608.
str
3
2
–
1
–1
(
5 cm (–C = N), 1482.2 cm (–CH ), 1297.0 (Ar–F), 1018.
2
2
–
1
3 c1m (Ar–Cl)
,
7
1
–
H-NMR: (CdCl ) δ 3.82(s, 3H, –OCH ), δ 4.22 (d (J
3
3
= 13.2), 1H, –CH ), δ 5.64 (d (J = 13.2) 1H, –CH ), δ 6.85
2
,
2
(d (J = 8.4), 1H, Ar–H), δ 6.95 (dd (J = 8.7, 9.3), 2H, Ar–H), δ
7.07 (t, 1H, Ar–H), δ 7.16–7.32 (m, 1H, Ar–H), δ 7.45–7.52
(m, 4H, Ar–H), δ 7.67 (t, 1H, Ar–H).
1
3
2
3
C–F
=
1
3
2
1
1
1
26.78, 129.40, 129.55, 129.70, 130.89, 131.40, 131.44,
32.37, 132.97, 133.04, 133.32, 134.57, 146.49,
C-NMR: (CdCl , 75 MHz) 46.34, 55.70, 116.38 (d, J
3 C–F
= 22.5), 118.93, 124.64, 129.24, 130.25, 131.58, 132.58,
1
1
57.331,159.42 (d, J
= 290), 165.41
133.37, 134.29, 157.22 (d, J
= 288.75) 165.38.
C–F
C–F
+
MS: m/z 472 (M , 20%), m/z 425 (22.3%, C H ClFNO),
Anal. calc. for C H BrClFN O; N, 11.26 Found: N,
23 15 4
1
5
13
m/z 321(76%, C H ClN ) m/z 286 (10%, C H ClFN ) m/z
11.20.
1
7
12
5
15 11
3
1
89(100%, C H N O )
9 7 3 2
Anal. calc. for C H ClFN O ; N, 17.77 Found: N, 17.75.
6.6. 8-Chloro-6-(2-fluorophenyl)-1-pyridin-3-yl-4H-[1,2,4]
triazolo[4,3-a][1,4]benzodiazepine
2
4
14
6 2
6
4
.3. 8-Chloro-6- (2-fluorophenyl)-1-(6-methoxy-2-naphthyl)-
H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
1
H-NMR: (CdCl ) δ 4.19 (d (J = 10.4), 1H, –CH ), δ 5.61
3 2
(
d (J = 10.4), 1H, –CH ), δ 6.92 (d (J = 6.8), 1H, Ar–H), δ
2
–
1
–1
FT-IR: (KBr): 3041.5 cm and 2964.1 cm (–CHstr),
7.05 (t, 1H, Ar–H), δ 7.30 (t, 1H, Ar–H), δ 7.30 (m, 3H, Ar–
H), δ 7.50 (s, 1H, Ar–H), δ 7.74 (s, 1H, Ar–H), δ 7.87(d (J
= 6.2), 1H, Ar–H), δ 8.72 (d (J = 3.2), 1H, Ar–H), δ 8.77 (s,
1H, Ar–H)
–
1
−1
–1
1
(
614.3 cm (–C = N), 1481.2 cm (–CH ), 1097.4 cm
2
–
1
Ar–F), 1026.1 cm (Ar–Cl).
1
H-NMR: (CdCl ) δ 3.95 (s, 3H, –OCH ), δ 4.22 (d (J
9.75) 1H, –CH ), δ 5.62 (d (J = 9.72) 1H, –CH ), δ 6.94
3
3
1
3
2
=
C-NMR: (CdCl , 125 MHz) 47.21,117.17 (d, JC–F
3
2
2
(
2
1
d (J = 6.51), 1H, Ar–H), δ 7.15 (m, 2H, Ar–H), δ 7.25 (m,
= 22.5), 123.74, 124.56, 125.65,126.55, 127.77, 127.86,
130.56, 131.67, 131.88, 132.46, 132.85, 133.72, 133.78,
134.96, 136.59, 149.89, 151.79, 152.18,159.12 (d, JC–F
H, Ar–H), δ 7.34 (m 2H, Ar–H), δ 7.45 (dd (J = 6.42,6.36),
,
1
H, Ar–H), δ 7.76 (t, 1H, Ar–H), δ 7.73–7.80 (m, 3H, Ar–H),
δ 8.07 (s, 1H, Ar–H)
= 280), 162.23,166.25
+
+
MS: m/z 469 (M , 74%) m/z 439 (10%, C H ClFNO), m/z
MS: m/z 390(M , 25%), m/z 415 ((M + 2) + Na, 20%), m/z
2
6 16
2
87 (20%, C H ClFN ) m/z 189(28%, C H N O )
430 (M + K, 18%), m/z 355 (M-Cl, 22%), m/z 295
(C H ClN , 20%), m/z 281 (C H ClN , 60%), m/z 207
1
5
11
3
9 7 3 2
Anal. calc. for C H ClFN O; N, 11.95, Found: N, 11.94.
2
7
18
4
15 10
5
14
8
5
(
C H ClN , 70%), m/z 147 (C H N , 100%).
9 8 4 9 10 2
6
.4. 8-Chloro-6-(2-fluorophenyl)-1-(4-fluorophenyl)-4H-
Anal. calc. for C H ClFN ; N, 17.97 Found: N, 17.95.
21 13 5
[
1,2,4]triazolo[4,3-a][1,4]benzodiazepine
7
. Conclusion
–
1
–1
FT-IR: (KBr): 3066.6 cm and 2925.8 cm (–CHstr),
–
1
–1
1
1
610.5 cm (–C = N), 1481 cm (–CH ), 1230.5 (Ar–F),
2
Six novel 8-chloro-6-(2-fluorophenyl)-1-(aryl)-4H-[1,2,4]
–
1
103.2 cm (Ar–Cl)
triazolo[4,3-a][1,4]benzodiazepines, which are structural analo-
gues of alprazolam and midazolam were synthesized and char-
acterized by spectral analysis. All the compounds were
1
H-NMR: (CdCl ) δ 4.19 (d (J = 13.2) 1H, –CH ), δ 5.58
d (J = 12.9), 1H, –CH ), δ 6.92 (d (J = 9.0), 1H, Ar–H), δ
2
3
,
2
(