Synthesis and antifungal activity
d: 163.26, 161.70, 158.64, 157.65, 150.43, 142.45, 141.31,
111.84, 109.17, 107.63, 103.05, 65.64, 62.79, 59.37, 58.22,
?
48.54, 18.33; LC–MS, m/z: 479.2 (M ? H) .
1
1
1
26.16, 122.17, 119.33, 117.68, 115.48, 114.54, 111.86,
09.95, 106.45, 103.28, 67.46, 63.02, 59.51, 58.51, 48.05,
?
8.02; LC–MS, m/z: 499.3 (M ? H) .
1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-
{
N-ethyl-N-[1-benzyl-1H-1,2,3-triazol-4-yl
methyl]amino}-2-propanol (1n)
1
{
-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-
N-ethyl-N-[1-(2-cyanobenzyl)-1H-1,2,3-triazol-4-yl
1
H NMR (300 MHz, CDCl ) d: 8.09 (1H, s, triazole–H),
3
methyl]amino}-2-propanol (1k)
7
.75 (1H, s, triazole–H), 7.54–7.58 (1H, m, Ar–H),
7.35–7.40 (4H, m, Ar–H), 7.05 (1H, s, triazole–H),
.72–6.79 (2H, m, Ar–H), 5.52 (H, s, Ar–CH –), 5.39(1H,
1
H NMR (300 MHz, CDCl ) d: 8.12 (1H, s, triazole–H),
3
6
2
7
6
4
.78 (1H, s, triazole–H), 7.38–7.66 (6H, m, Ar–H),
s, OH), 4.39–4.50 (2H, d, J = 14.4 Hz, triazole–CH –),
2
.75–6.84 (2H, m, Ar–H), 5.74 (2H, s, Ar–CH –),
2
3
.51–3.59 (2H, d, J = 14.4 Hz, triazole–CH –), 2.71–3.16
2
.40–4.55 (2H, d, J = 14.4 Hz, triazole–CH –), 3.52–3.63
2
*
2H, d, J = 13.8 Hz, CH ), 2.35–2.39 (2H, q, NCH CH ),
2 2 3
(
(
2H, d, J = 14.4 Hz, triazole–CH –), 2.71–3.21 (2H, d,
2
*
13
*
2
0.85–0.87 (3H, t, NCH CH ); C NMR (75 MHz, CDCl3)
2 3
J = 13.8 Hz, CH2), 2.34–2.41 (2H, q, NCH CH ),
3
*
13
d: 164.06, 161.30, 158.63, 157.75, 150.33, 143.25, 140.32,
0
.85–0.90 (3H, t, NCH CH ); C NMR (75 MHz, CDCl3)
2 3
1
1
1
26.24, 122.57, 119.27, 117.82, 115.06, 114.14, 111.83,
d: 162.15, 160.87, 157.46, 156.52, 150.16, 145.28, 141.20,
09.17, 107.34, 103.28, 65.67, 62.06, 59.55, 58.42, 48.05,
?
7.30; LC–MS m/z: 454.2 (M ? H) .
1
1
4
24.80, 122.65, 120.04, 119.62, 117.37, 115,51, 113.48,
12.24, 109.51, 107.20, 103.16, 66.23, 62.77, 59.06, 58.69,
?
7.35, 17.68; LC–MS, m/z: 479.2 (M ? H) .
1
{
-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-
N-ethyl-N-[1-(4-methoxy-benzyl)-1H-1,2,3-triazol-4-
1
{
-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-
yl methyl]amino}-2-propanol (1o)
N-ethyl-N-[1-(3-cyanobenzyl)-1H-1,2,3-triazol-4-yl
methyl]amino}-2-propanol (1l)
1
H NMR (300 MHz, CDCl ) d: 8.09 (1H, s, triazole–H),
3
7
.75 (1H, s, triazole–H), 7.54–7.58 (1H, m, Ar–H), 7.22
1
H NMR (300 MHz, CDCl ) d: 8.11 (1H, s, triazole–H), 7.79
3
(2H, d, J = 9.0 Hz, Ar–H), 7.02 (1H, s, triazole–H), 6.91
(2H, d, J = 9.0 Hz, Ar–H), 6.73–6.80 (2H, m, Ar–H), 5.45
(2H, s, Ar–CH –), 4.39–4.50 (2H, d, J = 14.4 Hz, tria-
(
1H, s, triazole–H), 7.51–7.68 (5H, m, Ar–H), 7.15 (1H, s,
triazole–H), 6.75–6.85 (2H, m, Ar–H), 5.59 (H, s, Ar–CH –),
2
2
4
.38–4.58 (2H, d, J = 14.1 Hz, triazole–CH –), 3.52–3.66
2
zole–CH –), 3.81 (3H, s, OCH3), 3.50–3.58 (2H, d,
2
(
2H, d, J = 14.4 Hz, triazole–CH –), 2.68–3.20 (2H, d,
2
J = 15.0 Hz, triazole–CH –), 2.70–3.16 (2H, d,
2
*
2
J = 14.1 Hz, CH2), 2.32–2.39 (2H, q, NCH CH ),
3
*
2
J = 13.8 Hz, CH2), 2.34–2.38 (2H, q, NCH CH ),
3
*
3
13
.85–0.90 (3H, t, NCH CH ); C NMR (75 MHz, CDCl3)
0
*
13
.85–0.87 (3H, t, NCH CH ); C NMR (75 MHz, CDCl3)
2
0
2 3
d: 163.76, 161.52, 158.13, 157.75, 150.44, 143.65, 140.21,
d: 162.19, 160.82, 157.30, 156.21, 150.01, 145.45, 141.21,
1
1
4
26.54, 122.77, 119.26, 118.32, 117.48, 115.92, 114.84,
1
1
4
24.54, 122.68, 119.56, 117.49, 115.55, 113.10, 112.11,
11.88, 109.95, 107.47, 103.09, 66.46, 63.04, 59.57, 58.55,
?
8.05, 18.05; LC–MS, m/z: 479.2 (M ? H) .
09.52, 107.32, 103.68, 66.87, 62.46, 59.39, 58.71, 55.47,
?
7.41, 17.85; LC–MS m/z: 484.2 (M ? H) .
1
{
-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-
1-(1H-1,2,4-triazol-1-yl)-2-(2, 4-difluorophenyl)-3-
{N-ethyl-N-[1-(2,4-dichlorobenzyl)-1H-1,2,3-triazol-4-
yl methyl]amino}-2-propanol (1p)
N-ethyl-N-[1-(4-cyanobenzyl)-1H-1,2,3-triazol-4-yl
methyl]amino}-2-propanol (1m)
1
1
H NMR(300 MHz, CDCl ) d: 8.10 (1H, s, triazole–H),
H NMR (300 MHz, CDCl ) d: 8.08 (1H, s, triazole–H), 7.67
3
3
7.76 (1H, s, triazole–H), 7.66–7.69 (1H, d, J = 8.4 Hz,
Ar–H), 7.56–7.64 (1H, m, Ar–H), 7.35–7.37 (1H, d,
(1H, s, triazole–H), 7.50–7.54 (2H, m, Ar–H), 7.36 (1H, s,
triazole–H), 7.34–7.35 (2H, m, Ar–H), 7.04–7.18 (1H, m, Ar–
J = 8.4 Hz, Ar–H), 7.22 (1H, s, triazole–H), 6.75–6.84
2H, m, Ar–H), 5.62 (H, s, Ar–CH –), 4.40–4.58 (2H, d,
H), 6.65–6.75 (2H, m, Ar–H), 5.52 (H, s, Ar–CH –), 4.32–4.48
2
(
(2H, m, triazole–CH –), 3.44–3.55 (2H, d, J = 14.4 Hz, tria-
2
2
J = 14.1 Hz, triazole–CH –), 3.54–3.67 (2H, d,
2
zole–CH –), 2.64–3.11 (2H, m, CH ), 2.25–2.32 (2H, q,
2
2
*
*
13
J = 14.4 Hz, triazole–CH –), 2.72–3.21 (2H, d,
2
NCH CH ), 0.78–0.82 (3H, m, NCH CH ); C NMR
2 3 2 3
*
J = 14.1 Hz, CH2), 2.32–2.40 (2H, q, NCH CH ),
3
(75 MHz, CDCl ) d: 162.06, 161.30, 158.53, 157.44, 150.43,
2
3
*
3
13
.85–0.90 (3H, t, NCH CH ); C NMR (75 MHz, CDCl3)
0
143.35, 140.33, 126.12, 122.65, 119.10, 117.24, 115.36,
2
d: 162.83, 161.10, 158.65, 157.35, 150.42, 143.41, 140.37,
26.12, 122.47, 119.42, 118.32, 117.25, 115.33, 114.64,
114.56, 111.86, 109.25, 107.55, 103.28, 65.45, 63.50, 59.58,
?
58.32, 48.05, 18.57; LC–MS m/z: 522.2 (M ? H) .
1
123