Med Chem Res
1
3
6
(
.9 Hz, 3H, –CH3; C NMR: δ 21.1(CH –CH–), 21.1
4-(4-Pentylphenyl)-1-(1-(4-(3-phenyl-2,5-di-p-tolyl-1H-
pyrrol-1-yl)phenyl)ethyl)-1H-1,2,3-triazole (7s)
3
CH –Ar), 59.5 (–CH–), 110.1 (pyrrole-CH), 118.0 (Ar–C),
3
123.4 (Ar–C), 125.4 (Ar–C), 125.5 (Ar–C), 126.4 (Ar–C),
126.7 (Ar–C), 127.9 (Ar–C), 128.0 (Ar–C), 128.1 (Ar–C),
128.5 (Ar–C), 128.6 (Ar–C), 128.7 (Ar–C), 129.3 (Ar–C),
129.6 (Ar–C), 130.5 (Ar–C), 131.1 (Ar–C), 132.1 (Ar–C),
132.7 (Ar–C), 134.5 (Ar–C), 135.9 (Ar–C), 136.7 (Ar–C),
138.2 (Ar–C), 139.1 (Ar–C), 147.6 (Ar–C); IR (KBr): υ
7
62, 1077, 1273, 1599, 1657, 2986, 3031 cm−1; ESI-MS:
1
White solid, mp: 137–139 °C; yield: 89%; H NMR: δ 7.70
(d, J = 8.3 Hz, 2H, Ar–H), 7.43 (s, 1H, triazole-H), 7.24 (d,
J = 8.3 Hz, 2H, Ar–H), 7.19–7.06 (m, 10H, Ar–H),
7.05–6.96 (m, 3H, Ar–H), 6.90 (qt, 4H, Ar–H), 6.67 (s, 1H,
Pyrrole- H), 5.82 (qt, 1H, –CH), 2.63, (t, 2H, –CH ), 2.30
(s, 3H, –CH ), 2.24 (s, 3H, –CH ), 1.96 (d, J = 7.5 Hz, 3H,
2
3
3
m/z: 571 [M + H]; HRMS (ESI) calcd for C H N ,
–CH3), 1.70–1.55 (m, 4H, –CH –), 1.41–1.28 (m, 2H,
4
0
35
4
2
1
3
5
71.28623 [M + H], found: 571.28620.
–CH2–), 0.89(s, 3H, –CH3);
C
NMR:
δ
13.9
(
(
(
(
(
CH –CH –), 21.0 (CH –CH–), 21.0 (CH –Ar), 21.1
3
2
3
3
CH –Ar), 22.4 (–CH –), 31.0 (–CH –), 31.3 (–CH –), 35.6
3
2
2
2
–CH –), 59.4 (CH –CH–), 110.1 (pyrrole-CH), 117.7
2
3
2
-(1-(1-(4-(3-Phenyl-2,5-di-p-tolyl-1H-pyrrol-1-yl)phenyl)
Ar–C), 123.3 (Ar–C), 125.4 (Ar–C), 126.3 (Ar–C), 126.6
Ar–C), 127.9 (Ar–C), 128.5 (Ar–C), 128.8 (Ar–C), 129.4
ethyl)-1H-1,2,3-triazol-4-yl)ethanol (7q)
1
(Ar–C), 129.6 (Ar–C), 131.1 (Ar–C), 131.8 (Ar–C), 132.7
White solid, m.p. 90–92 °C; yield: 83%; H NMR: δ
.62–6.75 (m, 18H, Ar–H), 6.67 (s, 1H, pyrrole- H), 5.76
qt, 1H, –CH), 4.24–3.72(m, 1H, CH OH), 2.91 (t, J = 3.9
(
(
(
Ar–C), 132.9 (Ar–C), 134.4 (Ar–C), 134.9 (Ar–C), 136.6
Ar–C), 138.2 (Ar–C), 139.1(Ar–C), 143.0 (Ar–C), 147.7
7
(
2
Ar–C); IR (KBr): υ 760, 1080, 1213, 1490, 1598, 2919,
Hz, 2H, –CH ) 2.27, (s, 6H, –CH ), 1.91 (d, J = 6.2 Hz, 3H,
2
3
−1
1
3
3048 cm ; ESI-MS: m/z: 641 [M + H]; HRMS (ESI) calcd
for C45 H45 N4, 641.36558 [M + H], found: 641.36568.
–
CH3); C NMR: δ 21.0 (CH –CH–), 21.1 (CH –Ar), 21.2
3 3
(
CH –Ar), 29.6 (–CH –), 59.7 (–CH–), 61.4 (–CH –OH),
3 2 2
1
10.1 (pyrrole-CH), 123.3 (Ar–C), 126.3 (Ar–C), 126.5
3
1
-(1-(1-(4-(2,3,5-Triphenyl-1H-pyrrol-1-yl)phenyl)ethyl)-
H-1,2,3-triazol-4-yl)pyridine (7t)
(
(
(
(
(
Ar–C), 127.8 (Ar–C), 128.5 (Ar–C), 128.5 (Ar–C), 128.8
Ar–C), 129.3 (Ar–C), 129.5 (Ar–C), 131.1 (Ar–C), 131.8
Ar–C), 132.7 (Ar–C), 132.9 (Ar–C), 134.4 (Ar–C), 134.9
Ar–C), 136.6 (Ar–C), 138.2 (Ar–C), 139.1 (Ar–C); IR
1
White solid, m.p. 130–132 °C; yield: 88%; H NMR: δ 8.58
(d, J = 4.5 Hz, 1H, pyridine-H), 8.18 (d, J = 7.1 Hz, 1H,
pyridine-H), 7.95 (s, 1H, pyridine-H), 7.77 (t, 1H, pyridine-
H), 7.28–7.05 (m, 17H, Ar–H), 7.04–6.95 (m, 3H, Ar–H),
6
6
−1
KBr): υ 760, 1069, 1239, 1484, 1657, 2987, 3048 cm
;
ESI-MS: m/z: 538 [M + H]; HRMS (ESI) calcd for C36
H ON , 539.28054 [M + H], found: 539.28002.
3
5
4
.70 (s, 1H, pyrrole- H), 5.86 (qt, 1H, –CH), 1.96 (d, J =
1
3
.7 Hz, 3H, –CH3); C NMR: δ 21.1 (CH –CH–), 59.6
3
(
–CH–), 110.1 (pyrrole-CH), 120.1 (Ar–C), 120.6 (Ar–C),
1
-(1-(4-(3-Phenyl-2,5-di-p-tolyl-1H-pyrrol-1-yl)phenyl)
1
1
1
1
1
1
7
22.8 (Ar–C), 123.6 (Ar–C), 125.5 (Ar–C), 126.5 (Ar–C),
26.6 (Ar–C), 127.1 (Ar–C), 127.9 (Ar–C), 128.0 (Ar–C),
28.0 (Ar–C), 128.5 (Ar–C), 129.5 (Ar–C), 131.3 (Ar–C),
32.0 (Ar–C), 132.3 (Ar–C), 132.5 (Ar–C), 134.7(Ar–C),
35.8 (Ar–C), 136.9 (Ar–C), 138.2 (Ar–C), 139.0 (Ar–C),
48.2 (Ar–C), 149.2 (Ar–C), 150.1 (Ar–C); IR (KBr): υ
ethyl)-4-p-tolyl-1H-1,2,3-triazole (7r)
1
White solid, m.p. 203–205 °C; yield: 92%; H NMR: δ 7.60
d, J = 8.1 Hz, 2H, Ar–H), 7.36 (s, 1H, triazole-H) 7.16 (d,
J = 9.0 Hz, 2H, Ar–H), 7.08–6.98 (m, 10H, Ar–H),
.97–6.89 (m, 3H, Ar–H), 6.85–6.81 (m, 4H, Ar–H), 6.59
s, 1H, pyrrole-H), 5.74 (qt, 1H, –CH), 2.30, (s, 3H, –CH3),
(
−
1
6
(
58, 1078, 1180, 1483, 1600, 2924, 3051 cm ; ESI-MS:
m/z: 544 [M + H].
2
3
2
.22 (s, 3H, –CH ), 2.17 (s, 3H, –CH ), 1.88 (d, J = 6.9 Hz,
3 3
1
3
H, –CH3); C NMR: δ 21.0 (CH –CH–), 21.1 (CH –Ar),
3
3
4-Phenyl-1-(1-(4-(2,3,5-triphenyl-1H-pyrrol-1-yl)phenyl)
ethyl)-1H-1,2,3-triazole (7u)
1.1 (CH –Ar), 21.2 (CH –Ar), 59.5 (–CH–), 110.1 (pyr-
3
3
role-CH), 117.7 (Ar–C), 123.3 (Ar–C), 125.4 (Ar–C), 126.3
1
(
(
(
(
(
(
Ar–C), 126.7 (Ar–C), 127.7 (Ar–C), 127.9 (Ar–C), 128.5
Ar–C), 128.5 (Ar–C), 128.8 (Ar–C), 129.4 (Ar–C), 129.6
Ar–C), 131.1 (Ar–C), 131.8 (Ar–C), 132.7 (Ar–C), 132.9
Ar–C), 134.4 (Ar–C), 134.9 (Ar–C), 136.6 (Ar–C), 137.9
Ar–C), 138.2 (Ar–C), 139.2 (Ar–C), 147.7 (Ar–C); IR
White solid, m.p. 161–164 °C; yield: 92%; H NMR: δ 7.79
(
=
7
(
d, J = 7.1 Hz,2H, Ar–H), 7.46 (s, 1H, triazole-H) 7.43 (t, J
7.7 Hz, 2H, Ar–H), 7.34 (t, J = 7.4 Hz, 1H, Ar–H),
.26–7.09 (m, 15H, Ar–H), 7.08–6.99 (m, 4H, Ar–H), 6.70
s, 1H, pyrrole-H), 5.82 (qt, 1H, –CH), 1.97 (d, J = 7.0 Hz,
−1
1
3
KBr): υ 695, 1076, 1224, 1491, 1599, 2919, 3023 cm
;
3
1
(
H, –CH3); C NMR: δ 21.1 (CH –CH–), 59.5 (–CH–),
3
ESI-MS: m/z: 585 [M + H]; HRMS (ESI) calcd for C41
H37 N4, 585.30127 [M + H], found: 585.30227.
10.1 (pyrrole-CH), 118.1 (Ar–C), 123.6 (Ar–C), 125.5
Ar–C), 126.5 (Ar–C), 126.7 (Ar–C), 127.1 (Ar–C), 127.8