SYNTHESIS OF 1-SUBSTITUTED 3-ALKYL-1,2,3-TRIAZOL-3-IUM-5-OLATES
881
7
11
14
18
1
1
29.4 d (C , C , J = 160.4 Hz), 129.1 d (C , C , J =
(2H, CH ), 3.90 s (3H, CH ). Found, %: N 13.08.
C H N O . Calculated, %: N 13.08.
24 20 4 2
2
3
9
16
58.7 Hz), 128.7 d (C , J = 156.0 Hz), 124.0 d (C ,
J = 159.9 Hz), 121.3 d (C , C , J = 163.7 Hz), 119.4 d
C , C , J = 159.5 Hz), 111.3 t (C , J = 1.2 Hz),
8
10
3
-Phenacyl-1-phenyl-4-phenylcarbamoyl-1H-
15
17
4
(
6
4
1
,2,3-triazol-3-ium-5-olate (IIIg). Yield 0.27 g (67%),
2
1
8.2 d (C , J = 147.8 Hz), 56.9 t (C , J = 146.0 Hz),
1
mp 184°C. H NMR spectrum, δ, ppm: 10.28 s (1H,
3
6.9 t (C , J = 151.0 Hz). Found, %: N 16.8.
NH), 8.12 d (2H, H , J = 7.1 Hz), 8.03–8.00 m (2H,
arom
C H N O . Calculated, %: N 16.66.
18
16
4
3
Harom), 7.77 t (1H, Harom, J = 7.4 Hz), 7.65 t (4H, Harom
J = 7.5 Hz), 7.58–7.53 m (3H, Harom), 7.33 t (2H, Harom
,
,
3
-Methyl-1-phenyl-4-phenylcarbamoyl-1H-1,2,3-
triazol-3-ium-5-olate (IIIb). Yield 0.22 g (76%),
J = 7.5 Hz), 7.10 t (2H, Harom, J = 7.4 Hz), 6.51 s
1
+
mp 150°C. H NMR spectrum, δ, ppm: 10.36 s (1H,
(2H, CH ). Mass spectrum: m/z 398 [M] . Found, %:
2
NH), 7.98 d (2H, H , J = 7.5 Hz), 7.63 d (2H, H
,
N 13.89. C H N O . Calculated, %: N 14.06.
arom
arom
23 18
4
2
J = 7.5 Hz), 7.57 t (2H, Harom, J = 7.5 Hz), 7.46 t (1H,
Harom, J = 7.5 Hz), 7.33 t (2H, Harom, J = 7.5 Hz), 7.08 t
3
-Acetonyl-1-phenyl-4-phenylcarbamoyl-1H-
1
(
(
,2,3-triazol-3-ium-5-olate (IIIh). Yield 0.23 g
(
1H, Harom, J = 7.5 Hz), 4.41 s (3H, CH ). Found, %:
1
3
67%), mp 184°C. H NMR spectrum, δ, ppm: 10.23 s
N 18.81. C H N O . Calculated, %: N 19.04.
16
14
4
2
1H, NH), 8.00 d (2H, H , J = 7.3 Hz), 7.59 t
arom
3
-Ethyl-1-phenyl-4-phenylcarbamoyl-1H-1,2,3-
(4H, Harom, J = 7.0 Hz), 7.48 t (1H, Harom, J = 7.3 Hz),
7.33 d (2H, Harom, J = 7.3 Hz), 7.08 t (1H, Harom, J =
7.3 Hz), 5.74 s (2H, CH ), 2.37 s (3H, CH ). Found, %:
triazol-3-ium-5-olate (IIIc). Yield 0.25 g (82%),
1
mp 140°C. H NMR spectrum, δ, ppm: 10.46 s (1H,
2
3
NH), 8.00 d (2H, H , J = 7.5 Hz), 7.65–7.55 m (4H,
N 16.78. C H N O . Calculated, %: N 16.66.
arom
18 16 4 2
Harom), 7.46 t (1H, Harom, J = 7.4 Hz), 7.33 t (2H, Harom
,
3
-Ethoxycarbonylmethyl-1-phenyl-4-phenylcar-
J = 7.5 Hz), 7.08 t (1H, Harom, J = 7.4 Hz), 4.86 q (2H,
CH , J = 7.2 Hz), 1.61 t (3H, CH , J = 7.2 Hz). Found,
bamoyl-1H-1,2,3-triazol-3-ium-5-olate (IIIi). Yield
1
2
3
0
1
.17 g (46%), mp 142°C. H NMR spectrum, δ, ppm:
%
: N 18.18. C H N O . Calculated, %: N 18.17.
17 16 4 2
0.24 s (1H, NH), 7.98 d (2H, H , J = 7.7 Hz), 7.67–
arom
3
-Butyl-1-phenyl-4-phenylcarbamoyl-1H-1,2,3-
7.61 m (4H, Harom), 7.55 t (1H, Harom, J = 7.5 Hz),
7.38 t (2H, Harom, J = 7.7 Hz), 7.14 t (1H, Harom, J =
triazol-3-ium-5-olate (IIId). Yield 0.27 g (79%),
–
1
1
mp 110°C. IR spectrum: ν 1680 cm (C=O). H NMR
spectrum, δ, ppm: 10.47 s (1H, NH), 7.98 d.d (2H,
7.3 Hz), 5.70 s (2H, CH ), 4.24 q (2H, CH , J =
2 2
7.0 Hz), 1.25 t (3H, CH , J = 7.0 Hz). Mass spectrum:
3
+
H
, J = 7.5, 1.3 Hz), 7.65–7.55 m (4H, H ), 7.46 t
m/z 366 [M] . Found, %: N 15.15. C19H N O . Calcu-
18 4 2
arom
arom
(
1H, Harom, J = 7.4 Hz), 7.33 d (2H, Harom, J = 7.5 Hz),
lated, %: N 15.29.
7
.08 t (1H, Harom, J = 7.4 Hz), 4.82 t (2H, CH , J =
2
1
-Phenyl-4-phenylcarbamoyl-3-(4-piperidinyl-
7.2 Hz), 1.98 p (2H, CH , J = 7.4 Hz), 1.48–1.42 m
2
methyl)-1H-1,2,3-triazol-3-ium-5-olate (IIIj). Yield
–1
(
2H, CH ), 1.00 t (3H, CH , J = 7.3 Hz). Found, %:
2 3
0.22 g (56%), mp 208°C. IR spectrum: ν 1690 cm
1
N16.81. C H N O . Calculated, %: N 16.65.
19
20
4
2
(C=O). H NMR spectrum, δ, ppm: 10.47 s (1H, NH),
1
1
0.17 br.s (1H, NH), 7.97 d.d (2H, H , J = 7.4,
3
-Benzyl-1-phenyl-4-phenylcarbamoyl-1H-1,2,3-
arom
.2 Hz), 7.68–7.52 m (5H, Harom), 7.42–7.37 m (2H,
Harom), 7.15 d.d (1H, Harom, J = 7.4, 1.1 Hz), 5.26 t
2H, CH , J = 5.8 Hz), 3.76–3.40 m (4H, CH ),
.02 br.s (2H, CH ), 1.83–1.42 m (6H, CH ). Found,
triazol-3-ium-5-olate (IIIe). Yield 0.27 g (73%),
1
mp 140°C. H NMR spectrum, δ, ppm: 10.49 s (1H,
(
3
%
NH), 7.97 d (2H, H , J = 8.5 Hz), 7.64–7.60 m
2
2
arom
(
(
4H, Harom), 7.54–7.48 m (3H, Harom), 7.41–7.35 m
5H, Harom), 7.13 t (1H, Harom, J = 7.4 Hz), 6.07 s (2H,
2
2
: N 15.80. C H N O . Calculated, %: N 16.37.
22 25 5 2
CH ). Found, %: N 15.18. C H N O . Calculated, %:
N 15.13.
3-Methyl-1-p-tolyl-4-p-tolylcarbamoyl-1H-1,2,3-
2
22 18
4
2
triazol-3-ium-5-olate (IIIk). Yield 0.25 g (75%),
1
mp 218°C. H NMR spectrum, δ, ppm: 10.28 s (1H,
3
-p-Methoxyphenacyl-1-phenyl-4-phenyl-
NH), 7.84 d (2H, H , J = 8.4 Hz), 7.50 d (2H, H
,
arom
arom
carbamoyl-1H-1,2,3-triazol-3-ium-5-olate (IIIf).
1
J = 8.5 Hz), 7.35 d (2H, Harom, J = 8.4 Hz), 7.12 d (2H,
Harom, J = 8.5 Hz), 4.38 s (3H, CH ), 2.41 s (3H, CH ),
Yield 0.21 g (50%), mp 180°C. H NMR spectrum, δ,
3
3
ppm: 10.30 s (1H, NH), 8.09 d.d (2H, H , J = 5.0,
arom
2
.31 s (3H, CH ). Found, %: N 17.48. C H N O .
3 18 18 4 2
1
.9 Hz), 8.02 d.d (2H, Harom, J = 7.4, 1.3 Hz), 7.65 t
2H, Harom, J = 7.4 Hz), 7.56 t (3H, Harom, J = 7.5 Hz),
.33 t (2H, Harom, J = 7.5 Hz), 7.16 d (2H, Harom
J = 7.5 Hz), 7.10 t (1H, Harom, J = 7.4 Hz), 6.45 s
Calculated, %: N 17.38.
(
7
,
3-Ethyl-1-p-tolyl-4-p-tolylcarbamoyl-1H-1,2,3-
triazol-3-ium-5-olate (IIIl). Yield 0.27 g (81%),
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 40 No. 6 2004