DOI: 10.3109/14756366.2014.940933
N-heteroarylsubstituted triazolosulfonamides
379
General procedure for the synthesis of
Azidosulfonamide (5)
(2H, m), 7.51 (2H, s, –NH ), 7.58–7.67 (2H, m), 7.97–8.00
2
(2H, d), 8.05–8.08 (2H, d), 8.97 (1H, s, triazole ring ¼C–H); C
NMR (75 MHz; ppm; DMSO) ꢂ 183.6, 158.5, 150.6, 144.5, 143.8,
13
Sulfonilamide (0.5 g, 3 mmol) was dissolved in 6 M HCI (10 mL),
ꢁ
1
3
39.0, 138.8, 128.2, 125.2, 124.1, 122.7, 120.7, 118.3, 111.7,
5.6; Anal. Calcd. For C H N O S: C, 53.26; H, 3.42; N, 18.27;
THF (5 mL) and DMF (5 mL) and cooled to 0 C. Sodium nitrite
(248 mg, 3.6 mmol) in 15 ml of cold water was added slowly to the
mixture and stirred for 25 min at 0 C. Then, sodium azide
1
7 13 5 4
O, 16.69; S, 8.36. Found: C, 53.56; H, 3.73; N, 18.49; O, 16.92;
S, 8.16.
ꢁ
(282 mg, 4.4 mmol) was added to the mixture and stirred
overnight at room temperature. The mixture was extracted with
ethyl acetate and washed with 1 M sodium hydroxide solution,
saturated NaHCO solution and brine, respectively. The organic
4
1
-(4-((5-Nitro-2,3-dioxoindolin-1-yl)methyl)-1H-1,2,3-triazol-
-yl)benzenesulfonamide (6d)
3
ꢁ
ꢀ1
phase was dried over MgSO , filtered and evaporated under Yield 80%; m.p.: 266–68 C; IR (ꢁ, cm ): 3400 (NH ), 3095
2
4
vacuum. The product was purified by crystallization from CHCl3. (¼C–H), 1615 (C¼O); 1336 (NO ), 1316 and 1157 (S¼O);
2
1
H NMR (300 MHz; ppm; DMSO) ꢂ 5.17 (2H, s, N–CH ), 7.43–
2
General procedure for the N-propargylation (3a–k)
7.46 (1H, d), 7.51 (2H, s, –NH ), 7.96–7.98 (2H, d), 8.01–8.04
2
(
2H, d), 8.27 (1H, s), 8.49–8.53 (1H, d), 8.94 (1H, s, triazole ring
13
C–H); C NMR (75 MHz; ppm; DMSO) ꢂ 181.5, 159.0, 154.8,
KOH (1 mmol) and TBAB (10%) were added to dissolved
compound (2) (1 mmol) in DMF and the mixture was cooled to
¼
1
1
2
1
44.5, 143.8, 143.4, 139.0, 133.6, 128.2, 122.8, 120.8, 119.8,
18.8, 112.2, 31.3; Anal. Calcd. For C H N O S: C, 47.66; H,
ꢁ
0
C. Then, propargil bromide (1.2 mmol) was added and stirred
1
7 12 6 6
overnight at room temperature. The mixture was extracted with
ethyl acetate and the product was purified by crystallization from
CHCl3.
.82; N, 19.62; O, 22,41; S, 7.49. Found: C, 47.86; H, 2.99; N,
9.88; O, 22,61; S, 7.74.
4
1
-(4-((5-Chloro-2,3-dioxoindolin-1-yl)methyl)-1H-1,2,3-triazol-
-yl)benzenesulfonamide (6e)
General procedure for the synthesis of
N-heteroarylsubstituted triazolosulfonamide
compounds (6a–k)
ꢁ
ꢀ1
Yield 82%; m.p.: 287–89 C; IR (ꢁ, cm ): 3388 (NH ), 3091
2
1
(
¼C–H), 1607 (C¼O), 829 (Cl); 1318 and 1156 (S¼O); H NMR
Sodium ascorbate (0.1 mmol) and CuSO4 (0.1 mmol) in water
were added to compound 5 (1.0 mmol) in DMF. Then compound
(300 MHz; ppm; DMSO) ꢂ 5.10 (2H, s, N–CH ), 7.24–7.26 (1H,
d), 7.53 (2H, s, –NH ), 7.66–7.72 (2H, d), 7.98–8.01 (2H, d),
2
2
3a–k was added to the mixture and stirred overnight at room
temperature. The mixture was extracted with ethyl acetate and
13
8
.05–8.08 (2H, d), 8.95 (1H, s, triazole ring ¼C–H); C NMR
(75 MHz; ppm; DMSO) ꢂ 182.5, 158.3, 149.1, 144.5, 143.7,
washed with saturated NH Cl solution. The product was purified
4
by washing with acetone.
1
3
39.0, 137.6, 128.3, 128.2, 124.7, 122.7, 120.8, 119.8, 113.5,
5.7; Anal. Calcd. For C H ClN O S: C, 48.87; H, 2.89;
1
7
12
5 4
Cl, 8.49; N, 16.76; O, 15.32; S, 7.67. Found: C, 49.05; H, 3.05;
Cl, 8.65; N, 16.96; O, 15.74; S, 7.96.
4-(4((1H-indol-1-yl)methyl)-1H-1,2,3-triazol-1-
yl)benzenesulfonamide (6a)
o
Yield 75%; m.p.: 250–52 C; IR (ꢁ, cm ): 3366 (NH ), 3146
ꢀ1
2
4-(4-((1,3-Dioxoisoindolin-2-yl)methyl)-1H-1,2,3-triazol-
1
1
(
¼C–H), 1312 and 1155 (S¼O); H NMR (300 MHz; ppm;
-yl)benzenesulfonamide (6f)
DMSO) ꢂ 5.55 (2H, s, N–CH ), 6.45 (1H, s), 6.98–7.03 (1H, t),
2
ꢁ
ꢀ1
Yield 78%; m.p.: 273–75 C; IR (ꢁ, cm ): 3467 (NH ), 3252
2
(
(
7
7
.10–7.15 (1H, t) 7.48(2H, s, –NH ), 7.51–7.62 (3H, m), 7.96–
2
1
¼C–H), 1716 (C¼O), 1314 and 1155 (S¼O); H NMR
.98 (2H, d), 8.05–8.07 (2H, d), 8.87 (1H, s, triazole ring ¼C–H);
C NMR (75 MHz; ppm; DMSO) ꢂ 145.7, 144.5, 139.1, 136.2,
29.3, 128.9, 128.1, 122.5, 121.9, 121.1, 121.0, 119.9, 110.7,
01.8, 31.37; Anal. Calcd. For C H N O S: C, 57.78; H,4.28;
1
3
300 MHz; ppm; DMSO) ꢂ 4.92 (2H, s, N–CH ), 7.50 (2H, s,
2
–
8
NH ), 7.80–7.95 (4H, m), 7.94–7.97 (2H, d) 8.05–8.08 (2H, d),
2
.89 (1H, s, triazole ring ¼C–H); C NMR (75 MHz; ppm;
1
1
1
3
1
7 15 5 2
DMSO) ꢂ 168.05, 144.7, 144.4, 135.4, 135.2, 132.3, 128.0, 124.0,
23.9, 120.8, 33.6; Anal. Calcd. For: C H N O S: C, 53.26;
N, 19.82; O, 9.05; S, 9.07. Found: C, 57.99; H, 4.58; N, 19.98; O,
9
1
.45; S, 9.46.
17 13 5 4
H, 3.42; N, 18.27; O, 16.69; S, 8.36. Found: C, 53.63; H, 3.72;
N, 18.63; O, 16.99; S, 8.62.
1
1
-((1-(4-Sulfamoylphenyl)-1H-1,2,3-triazol-4-yl)methyl)-
H-indole-3-carbaldehyde (6b)
4-(4-((10H-phenothiazin-10-yl)methyl)-1H-1,2,3-triazol-1-
yl)benzenesulfonamide (6g)
ꢁ
ꢀ1
Yield 70%; m.p.: 316–17 C; IR (ꢁ, cm ): 3398 (NH ), 3118
2
1
(
(
(
(
(
(
¼C–H), 2803 (C–H, aldehyde), 1320 and 1159 (S¼O); H NMR
ꢁ
ꢀ1
Yield 85%; m.p.: 230–32 C; IR (ꢁ, cm ): 3361 (NH ), 3062
2
(
300 MHz; ppm; DMSO) ꢂ 5.73 (2H, s, N–CH ), 7.24–7.40
2
1
¼C–H), 1320 and 1156 (S¼O); H NMR (300 MHz; ppm;
3H, m), 7.51 (2H, s, –NH ), 7.75–7.77 (1H, d), 7.98–8.01
2
DMSO) ꢂ 5.24 (2H, s, N–CH ), 6.91–7.01 (4H, m), 7.11–7.16
2
2H, d), 8.08–8.13 (2H, d), 8.46 (1H, s, olefinic¼C–H), 9.00
1
3
(
(
4H, m), 7.53 (2H, s, –NH ), 7.96–7.99 (2H, d), 8.10–8.13
2
2H, d), 8.84 (1H, s, triazole ring ¼C–H); C NMR (75 MHz;
1H, s, triazole ring ¼C–H), 9.95 (1H, s, –CHO); C NMR
1
3
75 MHz; ppm; DMSO) ꢂ 185.5, 144.6, 144.4, 141.5, 139.1,
ppm; DMSO) ꢂ 145.7, 144.6, 144.4, 139.1, 128.2, 128.1, 127.4,
23.4, 123.2, 122.5, 120.8, 116.4, 44.4; Anal. Calcd. For:
C H N O S : C, 57.91; H, 3.93; N, 16.08; O, 7.35; S, 14.72.
1
1
1
1
37.5, 128.2, 125.4, 124.4, 123.3, 123.1, 121.7, 121.0, 118.2,
12.0, 42.1; Anal. Calcd. For C H N O S: C, 56.68; H, 3.96; N,
1
1
8 15 5 3
8.36; O, 12.58; S, 8.41. Found: C, 56.48; H, 3.78; N, 18.56; O,
2.79; S, 8.71.
21 17 5 2 2
Found: C, 58.18; H, 3.83; N, 16.35; O, 7.62; S, 14.92.
4-(4-((2,3-Dioxoindolin-1-yl)methyl)-1H-1,2,3-triazol-1-
yl)benzenesulfonamide (6c)
4-(4-((1,3-Dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)methyl)-
1H-1,2,3-triazol-1-yl)benzenesulfonamide(6h)
ꢁ
ꢀ1
ꢁ
ꢀ1
Yield 78%; m.p.: 282–84 C; IR (ꢁ, cm ): 3367 (NH ), 3146 Yield 72%; m.p.: 306–08 C; IR (ꢁ, cm ): 3364 (NH
(
), 3101
2
2
1
1
¼C–H), 1743 (C¼O) 1322 and 1159 (S¼O); H NMR (¼C–H), 1707 (C¼O), 1326 and 1158 (S¼O); H NMR
300 MHz; ppm; DMSO) ꢂ 5.08 (2H, s, N–CH ), 7.12–7.23 (300 MHz; ppm; DMSO) ꢂ 5.42 (2H, s, N–CH ), 7.49 (2H, s,
(
2