Arch. Pharm. Chem. Life Sci. 2015, 348, 366–374
H. Akrami et al.
ARC HH PHARM
Archiv der Pharmazie
C
22
H
16ClFN
4
(390.84): C, 67.61; H, 4.13; N, 14.33 Found: C,
(m, 2H, H4,5), 7.45 (bs, 4H, H1,2,7,8), 7.27–7.26 (m, 3H, H3,6, and
H-triazole), 7.14–7.13 (m, 2H, Ar H2,6), 7.00–6.98 (m, 2H, Ar
6
7.32; H, 4.38; N, 14.70.
1
3
2 2 3
H3,5), 5.63 (s, 2H, CH Ar), 5.34 (s, 2H, N–CH ). C NMR (CDCl ,
9
-((1-(3-Chlorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-9H-
carbazole (6f)
Cream solid; yield 83%; mp 178–180°C; IR (ATR, cm ):
125 MHz) d: 142.4, 141.1, 130.9, 130.8, 127.1, 124.2, 124.1,
121.5, 120.6, 117.3, 117.1, 109.9, 54.6, 40.0. Anal. calcd. for
C H17FN (356.40): C, 74.14; H, 4.81; N, 15.72. Found: C, 73.88;
22 4
H, 4.55; N, 15.98.
ꢃ1
1
3
8
H
066, 1596, 1484, 1459; H NMR (500 MHz, CDCl
.12 (m, 3H, H4,5, and H-triazole), 7.74 (d, J ¼ 8.1 Hz, 2H,
3
) d: 8.14–
1,8), 7.46–7.43 (t, J ¼ 7.6 Hz, 2H, H3,6), 7.36 (bs, 2H, H2,7),
9-((1-(4-Chlorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-9H-
7
.30 (s, 1H, Ar H
2
), 7.21–7.18 (m, 3H, Ar H
4
,
5,6), 5.65 (s, 2H,
carbazole (6k)
1
3
ꢃ1
CH
2
Ar), 5.29 (s, 2H, N–CH
2
). C NMR (CDCl , 125 MHz) d:
3
White solid; yield 80%; mp 148–150°C; IR (ATR, cm ): 3068,
1594, 1484, 1452; H NMR (500 MHz, CDCl
1
1
1
44.0, 140.2, 131.0, 128.5, 128.1, 127.0, 126.1, 123.9, 122.7,
20.6, 119.4, 110.0, 52.3, 38.0. Anal. calcd. for C22 17ClN
3
) d: 8.11 (d,
H
4
J ¼ 7.6 Hz, 2H, H4,5), 7.46 (bs, 4H, H1,2,7,8), 7.27 (bs, 3H, H3,6, and
(
372.85): C, 70.87; H, 4.60; N, 15.03. Found: C, 70.52; H, 4.92;
H-triazole), 7.16–7.13 (m, 2H, Ar H3,5), 7.08 (d, J ¼ 7.6 Hz, 2H,
1
3
N, 15.42.
2 2
Ar H2,6), 5.63 (s, 2H, CH Ar), 5.35 (s, 2H, N–CH ). C NMR
(
CDCl
124.2, 121.5, 120.6, 115.9, 115.6, 109.9, 54.5, 40.0. Anal. calcd.
for C22 17ClN (372.85): C, 70.87; H, 4.60; N, 15.03. Found: C,
3
, 100 MHz) d: 141.1, 135.9, 133.9, 130.39, 130.37, 127.1,
9
-((1-(3-Methylbenzyl)-1H-1,2,3-triazol-4-yl)methyl)-9H-
carbazole (6g)
White solid; yield 78%; mp 189–191°C; IR (ATR, cm ): 2970,
H
4
ꢃ1
70.49; H, 4.28; N, 15.40.
1
1
653, 1597, 1485, 1460; H NMR (400 MHz, CDCl
3
) d: 8.09 (bs,
2
H, H4,5), 7.79 (bs, 2H, H1,8), 7.52–7.45 (m, 5H, H2,3,6,7, and H-
9-((1-(4-Bromobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-9H-
triazole), 7.19–7.10 (m, 2H, Ar H
2
,
5
), 6.93 (bs, 2H, Ar H4,6), 5.93
carbazole (6l)
1
3
ꢃ1
(
(
1
s, 2H, CH
CDCl
27.5, 127.0, 124.1, 121.6, 120.4, 108.8, 47.1, 38.5, 20.0. Anal.
calcd. for C23 (352.43): C, 78.38; H, 5.72; N, 15.90. Found:
C, 78.75; H, 5.96; N, 15.65.
2
Ar), 5.45 (s, 2H, N–CH
, 100 MHz) d: 142.1, 139.3, 137.8, 132.9, 132.2, 130.4,
2
), 2.26 (s, 3H, CH
3
). C NMR
White solid; yield 78%; mp 147–148°C; IR (ATR, cm ): 3073,
2923, 1594, 1486, 1452; H NMR (500 MHz, CDCl
J ¼ 7.4 Hz, 2H, H4,5), 8.06 (s, 1H, H-triazole), 7.74 (d, J ¼ 7.9 Hz,
2H, Ar H3,5), 7.53 (d, J ¼ 8.2 Hz, 2H, H1,8), 7.45 (t, J ¼ 7.7 Hz,
2H, H2,7), 7.22–7.18 (m, 4H, H3,6, and Ar H2,6), 5.66 (s, 2H,
1
3
3
) d: 8.14 (d,
20 4
H N
1
3
CH
143.9, 140.2, 135.8, 132.0, 130.5, 127.6, 126.1, 123.7, 122.6,
120.6, 119.4, 110.0, 52.4, 38.0. Anal. calcd. for C22 17ClN
2 2 3
Ar), 5.48 (s, 2H, N–CH ). C NMR (CDCl , 125 MHz) d:
9
-((1-(3-Methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)-9H-
carbazole (6h)
White solid; yield 79%; mp 151–152°C; IR (ATR, cm ): 3069,
H
4
ꢃ1
(372.85): C, 70.87; H, 4.60; N, 15.03. Found: C, 70.52; H, 4.28;
N, 15.38.
1
2
959, 1597, 1485, 1459; H NMR (500 MHz, CDCl
m, 2H, H4,5), 7.46 (s, 4H, H1,2,7,8), 7.26–7.14 (m, 4H, H3,6 and Ar
, and H-triazole), 6.83–6.63 (m, 3H, Ar H ), 5.63 (s, 2H,
3
) d: 8.10–8.08
(
H
5
2
,
4
,
6
9-((1-(4-Methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)-9H-
carbazole (6m)
White solid; yield 77%; mp 147–148°C; IR (ATR, cm ):
1611, 1514, 1485, 1458; H NMR (500 MHz, CDCl
1
3
CH
2
Ar), 5.34 (s, 2H, N–CH
2
), 3.69 (s, 3H, OCH
3
). C NMR (CDCl
3
,
ꢃ1
1
25 MHz) d: 161.1, 141.2, 136.9, 131.2, 127.1, 124.2, 121.5,
1
1
21.1, 120.5, 115.4, 114.3, 109.9, 56.3, 55.3, 40.0. Anal. calcd.
3
) d: 8.11–
for C23
H
20
N
4
O (368.43): C, 74.98; H, 5.47; N, 15.21. Found: C,
8.09 (m, 2H, H4,5), 7.71 (bs, 4H, H1,2,7,8), 7.46 (m, 3H, H3,6
and H-triazole), 7.10 (d, J ¼ 8.0 Hz, 2H, Ar H2,6), 6.82 (d,
J ¼ 8.0 Hz, 2H, Ar H3,5), 4.27–4.18 (m, 7H, CH Ar, N–CH and
, 100 MHz) d: 160.2, 141.1, 136.7,
132.9, 129.3, 127.1, 124.4, 121.5, 120.6, 115.9, 115.6,
109.9, 56.5, 55.4, 40.0. Anal. calcd. for C23 O (368.43):
,
7
4.72; H, 5.76; N, 15.45.
2
2
1
3
9
-((1-(3-Fluorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-9H-
3 3
–OCH ). C NMR (CDCl
carbazole (6i)
White solid; yield 85%; mp 180–182°C; IR (ATR, cm ): 3070,
ꢃ1
20 4
H N
1
1
2
595, 1486, 1452; H NMR (500 MHz, CDCl
H, H4,5), 7.47 (br s, 4H, H1,2,7,8), 7.27 (br s, 4H, H3,6 and Ar H
), 6.92–6.83 (m, 2H, Ar
3
) d: 8.12–8.10 (m,
C, 74.98; H, 5.47; N, 15.21. Found: C, 74.63; H, 5.79;
N, 15.53.
2
,
and H-triazole), 7.02–6.97 (m, 1H, Ar H
4,6), 5.64 (s, 2H, –CH Ar), 5.41 (s, 2H, –N
CDCl , 100 MHz) d: 144.1, 140.3, 140.2, 131.2, 131.0, 128.1,
27.2, 123.9, 122.6, 120.7, 119.4, 116.1, 115.9, 110.0, 47.2, 38.0.
(356.40): C, 74.14; H, 4.81; N, 15.72.
Found: C, 74.49; H, 4.50; N, 15.57.
5
1
3
H
(
1
2
9
–CH
2
). C NMR
9-((1-(4-Nitrobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-9H-
3
carbazole (6n)
ꢃ1
Cream solid; yield 83%; mp 176–178°C; IR (ATR, cm ): 2925,
1598, 1515, 1485, 1454; H NMR (500 MHz, CDCl
1
Anal. calcd. for C22
H
17FN
4
3
) d: 8.15–8.11
(m, 6H, H1,4,5,8, and Ar H3,5), 7.45 (m, 7H, H2,3,6,7, and Ar H2,6),
1
3
5
2 2 3
.66 (s, 2H, CH Ar), 5.29 (s, 2H, N–CH ). C NMR (CDCl ,
9
-((1-(4-Fluorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-9H-
carbazole (6j)
White solid; yield 83%; mp 186–187°C; IR (ATR, cm ): 3063,
100 MHz) d 142.4, 141.1, 129.6, 127.1, 125.3, 124.9, 124.2,
121.6, 120.7, 115.9, 115.6, 109.8, 54.2, 30.8. Anal. calcd. for
C H N O (383.40): C, 68.92; H, 4.47; N, 18.27. Found: C,
22 17 5 2
68.60; H, 4.79; N, 18.58.
ꢃ1
1
1
601, 1508, 1483, 1451; H NMR (500 MHz, CDCl
3
) d: 8.10–8.08
ß 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.archpharm.com
372