Mol Divers
267 cm 1; MS (m/z, %): 390 (28.9, M ); Anal. calcd for
−
+
+
(29.4, M ); Anal. calcd for C H24N4O3: C 70.08, H 5.65,
25
1
C22H22N4O3: C 67.68, H 5.68, N 14.35, found: C 67.57, H
N 13.08, found: C 69.98, H 5.73, N 13.16.
5
.73, N 14.27.
1
3
-(4-((9H-Carbazol-9-yl)methyl)-1H-1,2,3-triazol-1-yl)-
-(4-chloro-3-methylphenoxy)propan-2-ol (10k)
1
3
-(4-((9H-Carbazol-9-yl)methyl)-1H-1,2,3-triazol-1-yl)-
-phenoxypropan-2-ol (10h)
Column chromatography on silica gel (EtOAc-n-hexane,
2
:1)gavecompound10kasacreamysolid(3.89g, 87%). mp:
Column chromatography on silica gel (EtOAc-n-hexane,
:1) gave compound 10h as a creamy solid (3.66 g, 92%).
◦
1
1
67−168 C; H NMR (250 MHz, CDCl3): δ = 2.25 (s, 3H,
2
CH3), 3.96-3.98 (m, 2H, NCH2CH), 4.22 (s, 1H, OH), 4.49–
◦
1
mp: 158−159 C; H NMR (250 MHz, CDCl3): δ = 3.95 (d,
4
6
.71 (m, 3H, OCH2, CHOH), 5.09 (s, 2H, NCH2C = C),
J = 4.8 Hz, 2H, NCH2CH), 4.22-4.23 (m, 1H, CHOH), 4.41
.81-6.85 (m, 3H, Ar-H), 7.13-7.30 (m, 8H, Ar-H), 7.77 ppm
(s, 1H, OH), 4.46 (dd, J = 7.0, 13.4 Hz, 1H, OCHAHB),
13
(
s, 1H, C(5)-H of triazole); C NMR (62.5 MHz, CDCl3) :
4.66 (dd, J = 2.5, 13.2 Hz, 1H, OCHA HB), 5.09 (s, 2H,
δ = 20.4, 58.7, 63.9, 66.8, 71.4, 111.5, 113.5, 117.6, 119.9,
NCH2C = C), 6.83-6.85 (m, 5H, Ar-H), 7.13–7.25 (m, 8H,
Ar-H), 7.92 ppm (s, 1H, C(5)-H of triazole); 13C NMR (62.5
MHz, CDCl3): δ = 57.1, 64.9, 66.5, 72.4, 111.9, 115.0, 117.5,
1
1
1
20.7, 121.6, 122.8, 123.3, 125.9, 130.2, 131.7, 137.5,
44.4, 157.4 ppm; IR (KBr): ν = 3391, 3029, 2953, 1456,
−1
+
258, 762 cm ; MS (m/z, %): 446 (30.8, M ); Anal. calcd
1
18.8, 119.7, 120.4, 121.9, 123.2, 128.8, 130.4, 144.2, 158.9
for C H23ClN4O2: C 67.18, H 5.19, Cl 7.93, N 12.54, found:
C 67.25, H 5.29, Cl 8.02, N 12.65.
2
5
−1
ppm; IR (KBr): ν = 3264, 3050, 2925, 1463, 1239cm
;
+
MS (m/z, %): 398 (25.6, M ); Anal. calcd for C24H22N4O2:
C 72.34, H 5.57, N 14.06, found: C 72.23, H 5.50, N 14.17.
1-(4-((9H-Carbazol-9-yl)methyl)-1H-1,2,3-triazol-1-yl)-
3-(4-chlorophenoxy)propan-2-ol (10l)
1
3
-(4-((9H-Carbazol-9-yl)methyl)-1H-1,2,3-triazol-1-yl)-
-(p-tolyloxy)propan-2-ol (10i)
Column chromatography on silica gel (EtOAc-n-hexane,
:1) gave compound 10l as a creamy solid (3.94 g, 91%).
2
◦
1
mp: 110 − 111 C; H NMR (250 MHz, CDCl3): δ = 3.55
Column chromatography on silica gel (EtOAc-n-hexane,
1
(d, J = 5.0 Hz, 1H, NCHAHBCH), 3.63 (s, 1H, OH), 3.78
2
:1) gave compound 10i as a brown oil (3.75 g, 91%). H
NMR (250 MHz, CDCl3): δ = 2.15 (s, 3H, CH3), 3.91–3.94
m, 2H, NCH2CH), 4.08-4.11 (m, 1H, CHOH), 4.39 (s, 1H,
OH), 4.45 (dd, J = 6.6, 13.7 Hz, 1H, OCHAHB), 4.63 (dd, J
6.5, 13.6 Hz, 1H, OCHA HB), 5.13 (s, 2H, NCH2C = C),
.79-6.88 (m, 6H, Ar-H), 7.13–7.22 (m, 6H, Ar-H), 7.77 ppm
(d, J = 5.0 Hz, 1H, NCHA HBCH), 4.05 (dd, J = 5.0, 17.5
Hz, 2H, OCH2), 4.19-4.21 (m, 1H, CHOH), 5.33 (s, 2H,
NCH2C = C), 6.48-6.62 (m, 4H, Ar-H), 7.03–7.11 (m,
(
8
H, Ar-H), 7.90 ppm (s, 1H, C(5)-H of triazole); 13C NMR
=
6
(
62.5 MHz, CDCl3): δ = 59.6, 64.4, 65.9, 72.8, 113.1, 116.7,
118.5, 119.7, 120.6, 122.1, 124.2, 126.0, 130.2, 131.7, 144.8,
s, 1H, C(5)-H of triazole); 1 C NMR (62.5 MHz, CDCl3):
δ = 24.0, 58.2, 64.3, 65.9, 73.3, 112.5, 115.7, 118.6, 119.8,
20.5, 122.7, 124.0, 129.7, 131.0, 132.3, 144.4, 159.8 ppm;
3
(
1
57.3 ppm; IR (KBr): ν = 3228, 3100, 2937, 1595, 1228,
−1
+
755 cm ; MS (m/z, %): 432 (28.4, M ); Anal. calcd for
1
−
1
C24H21ClN4O2: C 66.59, H 4.89, Cl 8.19, N 12.94, found:
C 66.48, H 4.80, Cl 8.26, N 13.04.
IR (film): ν = 3379, 3058, 2923, 1468, 1276 cm ; MS (m/z,
%
+
): 412 (27.3, M ); Anal. calcd for C H24N4O2: C 72.80,
2
5
H 5.86, N 13.58, found: C 72.73, H 5.94, N 13.50.
1
3
-(4-((9H-Carbazol-9-yl)methyl)-1H-1,2,3-triazol-1-yl)-
-(2-chlorophenoxy)propan-2-ol (10m)
1
3
-(4-((9H-Carbazol-9-yl)methyl)-1H-1,2,3-triazol-1-yl)-
-(4-methoxyphenoxy)propan-2-ol (10j)
Column chromatography on silica gel (EtOAc-n-hexane,
1
2:1) gave compound 10m as a brown oil (3.85 g, 89%). H
Column chromatography on silica gel (EtOAc-n-hexane,
:1) gave compound 10j as a brown solid (3.94 g, 92%)
NMR (250 MHz, CDCl3): δ = 3.86-3.90 (m, 3H, NCH2CH),
4.21 (s, 1H, OH), 4.44(dd, J = 7.6, 13.8 Hz, 1H, OCHAHB),
4.59 (dd, J = 3.4, 13.8 Hz, 1H, OCHA HB), 5.13 (s, 2H,
NCH2C = C), 6.85 (d, J = 8.3 Hz, 2H, Ar-H), 7.07-7.29
3
◦
1
mp: 125−126 C; H NMR (250 MHz, CDCl3): δ = 2.05 (s,
H, OCH3), 3.94 (dd, J = 5.0, 10.2 Hz, 2H, NCH2CH), 4.04
s, 1H, OH), 4.12-4.18 (m, 3H, OCH2, CHOH), 5.70 (s, 2H,
3
(
1
3
(m, 10H, Ar-H), 8.18 ppm (s, 1H, C(5)-H of triazole);
C
NCH2C = C), 6.67-6.77(m, 4H, Ar-H), 7.20–7.23 (m, 4H,
Ar-H), 7.41-7.46 (m, 4H, Ar-H), 8.06 ppm (s, 1H, C(5)-H
of triazole); 13C NMR (62.5 MHz, CDCl3): δ = 56.0, 58.1,
NMR (62.5 MHz, CDCl3) : δ = 58.5, 64.8, 67.4, 70.7, 112.8,
116.6, 118.6, 119.4, 120.5, 121.6, 122.2, 123.0, 123.8, 128.0,
130.0, 131.7, 143.6, 151.5 ppm; IR (film): ν = 3423, 3026,
2981, 1486, 1263, 759 cm ; MS (m/z, %): 432 (30.1, M );
Anal. calcd for C24H21ClN4O2: C 66.59, H 4.89, Cl 8.19, N
12.94, found: C 66.64, H 4.96, Cl 8.31, N 13.01.
−1
+
6
1
=
2.3, 65.9, 71.0, 112.3, 115.6, 116.8, 118.9, 120.1, 121.6,
23.1, 124.3, 131.8, 144.0, 150.3, 159.9 ppm; IR (KBr): ν
−1
3235, 3045, 2948, 1462, 1246 cm ; MS (m/z, %): 428
1
23