10.1002/adsc.202000909
Advanced Synthesis & Catalysis
quantities: (4-hydroxyphenyl) boronic acid (43 mg). Eluent
system composed of hexane:ethyl acetate = 75:25. The title
compound was isolated as a white solid in a yield of 73%
(55 mg, 162 µmol). 1H NMR (500 MHz, CD3CN) δ 7.96 (s,
1H), 7.82 (d, J = 8.4 Hz, 2H), 7.37 (d, J = 8.1 Hz, 2H), 7.28
(d, J = 8.4 Hz, 2H), 7.13 (d, J = 16.1 Hz, 1H), 6.99 (s, 1H),
6.74 – 6.66 (m, 3H), 2.34 (s, 3H). 13C NMR (126 MHz,
CD3CN) δ 156.60, 146.59, 142.82, 136.95, 134.41, 130.22,
129.27, 128.56, 127.58, 126.95, 115.73, 115.14, 113.29,
20.39. HRMS (ESI) m/z: [M+H] calcd for C18H17N2O3S
341.09740; found 341.09599.
The title compound was isolated as a white solid in a yield
1
of 53% (41 mg, 117 µmol). H NMR (500 MHz, CDCl3) δ
8.01 (d, J = 0.8 Hz, 1H), 7.86 (dt, J = 8.5, 1.7 Hz, 2H), 7.66
(d, J = 8.1 Hz, 1H), 7.64 (dd, J = 7.8, 1.0 Hz, 1H), 7.59 –
7.52 (m, 2H), 7.38 (d, J = 8.5 Hz, 3H), 7.32 (td, J = 7.7, 1.1
Hz, 1H), 7.10 (d, J = 16.0 Hz, 1H), 2.45 (s, 3H). 13C NMR
(214 MHz, CDCl3) δ 146.54, 141.90, 140.00, 137.08,
133.38, 132.74, 130.55, 130.03, 129.04, 127.71, 127.45,
125.95, 125.91, 123.48, 117.97, 115.19, 21.76. HRMS
(ESI) m/z: [M+Na] calcd for C19H15NaN3O2S 372.07827;
found 372.07855.
(E)-1-tosyl-4-(2,4,6-trimethylstyryl)-1H-imidazole
[NEW] (3k). The title compound was synthesized
according to the general procedure B using the following
conditions and quantities: mesitylboronic acid (73 mg). The
title compound was isolated as a yellow oil in a yield of 41%
(33 mg, 90 µmol).1H NMR (500 MHz, CDCl3) δ 8.00 (s,
1H), 7.85 (d, J = 8.4 Hz, 2H), 7.39 – 7.33 (m, 3H), 7.19 (s,
1H), 6.87 (s, 2H), 6.38 (d, J = 16.4 Hz, 1H), 2.45 (s, 3H),
2.31 (s, 6H), 2.27 (s, 3H). 13C NMR (126 MHz, CDCl3) δ
142.90, 141.76, 136.86, 136.51, 136.21, 131.97, 130.47,
128.78, 128.69, 127.44, 123.24, 117.26, 113.46, 21.75,
21.07, 20.94. HRMS (ESI) m/z: [M+H] calcd for
C21H23N2O2S 367.14802; found 367.14769.
(E)-4-(2-(1-tosyl-1H-imidazol-4-yl)vinyl)benzaldehyde
[NEW] (3p). The title compound was synthesized
according to the general procedure A using the following
conditions and quantities: (4-formyl-phenyl)boronic acid
(46 mg). Eluent system composed of hexane:ethyl acetate =
87:13. The title compound was isolated as a white solid in a
yield of 95% (74 mg, 210 µmol).1H NMR (500 MHz,
CDCl3) δ 9.97 (s, 1H), 8.01 (s, 1H), 7.90 – 7.79 (m, 4H),
7.59 (d, J = 8.2 Hz, 2H), 7.40 – 7.34 (m, 3H), 7.32 (s, 1H),
7.02 (d, J = 16.0 Hz, 1H), 2.44 (s, 3H). 13C NMR (126 MHz,
CD3CN) δ 186.27, 141.24, 137.55, 136.82, 131.86, 130.17,
129.44, 125.23, 124.92, 123.74, 122.10, 121.63, 116.25,
109.87, 16.45. HRMS (ESI) m/z: [M+H] calcd for
C19H17N2O3S 353.09599; found 353.09772.
(E)-4-(4-methoxystyryl)-1-tosyl-1H-imidazole [NEW]
(3l). The title compound was synthesized according to the
general procedure A using the following conditions and
quantities: (4-methoxyphenyl) boronic acid (47 mg). Eluent
system composed of hexane:ethyl acetate = 87:13. The title
compound was isolated as a white solid in a yield of 91%
(72 mg, 203 µmol).1H NMR (500 MHz, CDCl3) δ 7.98 (d, J
= 0.6 Hz, 1H), 7.83 (dt, J = 8.4, 1.9 Hz, 2H), 7.37 (ddd, J =
16.0, 7.6, 4.9 Hz, 4H), 7.30 – 7.24 (m, 1H), 7.20 (d, J = 0.9
Hz, 1H), 6.87 (dt, J = 8.8, 1.9 Hz, 2H), 6.73 (d, J = 16.1 Hz,
1H), 3.81 (s, 3H), 2.43 (s, 3H). 13C NMR (126 MHz, CDCl3)
δ 159.49, 146.29, 143.08, 134.97, 130.44, 130.08, 129.57,
127.80, 127.34, 116.13, 114.51, 114.13, 113.30, 55.31,
21.72. HRMS (ESI) m/z: [M+H] calcd for C19H19N2O3S
355.11164; found 355.11280.
(E)-4-(2-([1,1'-biphenyl]-2-yl)vinyl)-1-tosyl-1H-
imidazole [NEW] (3q). The title compound was
synthesized according to the general procedure B using the
following conditions and quantities: [1,1'-biphenyl]-2-
ylboronic acid (88 mg). The title compound was isolated as
a white solid in a yield of 65% (58 mg, 145 µmol).1H NMR
(850 MHz, CDCl3) δ 7.92 (d, J = 0.8 Hz, 1H), 7.82 (dt, J =
8.5, 1.8 Hz, 2H), 7.66 (dd, J = 7.5, 1.0 Hz, 1H), 7.42 – 7.39
(m, 2H), 7.37 – 7.31 (m, 7H), 7.29 (d, J = 16.0 Hz, 1H), 7.18
(d, J = 1.2 Hz, 1H), 6.81 (d, J = 16.0 Hz, 1H), 2.44 (s, 3H).
13C NMR (214 MHz, CDCl3) δ 146.31, 142.99, 141.36,
140.73, 136.82, 134.91, 134.89, 130.45, 130.43, 129.78,
129.49, 128.18, 127.73, 127.50, 127.39, 127.19, 127.16,
125.87, 119.52, 113.70, 21.74. HRMS (ESI) m/z: [M+H]
calcd for C24H22N2O2S 401.13237; found 401.13287.
(E)-4-(3-methoxystyryl)-1-tosyl-1H-imidazole [NEW]
(3m). The title compound was synthesized according to the
general procedure A using the following conditions and
quantities: (3-methoxyphenyl) boronic acid (47 mg). Eluent
system composed of hexane:ethyl acetate = 87:13. The title
compound was isolated as a white solid in a yield of 85%
(67 mg, 189 µmol).1H NMR (500 MHz, CDCl3) δ 7.99 (d, J
= 0.6 Hz, 1H), 7.83 (dt, J = 8.4, 1.7 Hz, 2H), 7.39 – 7.21 (m,
6H), 7.05 (d, J = 7.7 Hz, 1H), 7.00 – 6.97 (m, 1H), 6.86 (d,
J = 16.0 Hz, 1H), 6.83 – 6.79 (m, 1H), 3.82 (s, 3H), 2.44 (s,
3H). 13C NMR (126 MHz, CDCl3) δ 159.85, 146.38, 142.70,
138.22, 136.96, 134.91, 130.48, 130.40, 129.65, 127.37,
119.25, 118.56, 114.01, 113.55, 111.80, 55.22, 21.74.
HRMS (ESI) m/z: [M+H] calcd for C19H19N2O3S
355.11164; found 355.11180.
(E)-4-(4-iodostyryl)-1-tosyl-1H-imidazole [NEW] (3r).
The title compound was synthesized according to the
general procedure A using the following conditions and
quantities: (4-Iodophenyl)boronic acid (77 mg). Eluent
system composed of hexane:ethyl acetate = 90:10. The title
compound was isolated as a white solid in a yield of 71%
(71 mg, 158 µmol).1H NMR (500 MHz, CDCl3) δ 7.99 (s,
1H), 7.83 (dt, J = 8.4, 1.7 Hz, 2H), 7.65 (dt, J = 8.4, 1.8 Hz,
2H), 7.36 (d, J = 8.5 Hz, 2H), 7.23 (d, J = 16.3 Hz, 2H), 7.18
(dt, J = 8.8, 1.9, 1.9 Hz, 2H), 6.86 (d, J = 16.0 Hz, 1H), 2.44
(s, 3H). 13C NMR (126 MHz, CDCl3) δ 146.44, 142.42,
137.77, 137.03, 136.30, 134.86, 130.49, 129.31, 128.22,
127.38, 118.99, 114.32, 93.12, 21.75. HRMS (ESI) m/z:
[M+H] calcd for C18H16IN2O2S 450.99772; found
450.99980.
(E)-4-(2-methoxystyryl)-1-tosyl-1H-imidazole [NEW]
(3n). The title compound was synthesized according to the
general procedure A using the following conditions and
quantities: (2-methoxyphenyl) boronic acid (47 mg). Eluent
system composed of hexane:ethyl acetate = 87:13.The title
compound was isolated as a white solid in a yield of 71%
(56 mg, 158 µmol). 1H NMR (500 MHz, CDCl3) δ 7.99 (d,
J = 0.6 Hz, 1H), 7.83 (dt, J = 8.4, 1.6 Hz, 2H), 7.60 (d, J =
16.3 Hz, 1H), 7.47 (dd, J = 7.6, 1.6 Hz, 1H), 7.35 (d, J = 8.2
Hz, 2H), 7.25 – 7.20 (m, 2H), 6.97 – 6.91 (m, 2H), 6.88 (d,
J = 8.2 Hz, 1H), 3.86 (s, 3H), 2.44 (s, 3H). 13C NMR (126
MHz, CDCl3) δ 157.22, 146.26, 143.49, 136.88, 135.01,
130.43, 128.87, 127.34, 127.11, 125.81, 125.78, 120.63,
119.08, 113.58, 110.92, 55.38, 21.72. HRMS (ESI) m/z:
(E)-4-(4-fluorostyryl)-1-tosyl-1H-imidazole [NEW] (3s).
The title compound was synthesized according to the
general procedure A using the following conditions and
quantities: (4-fluorophenyl) boronic acid (43 mg). Eluent
system composed of hexane:ethyl acetate = 90:10. The title
compound was isolated as a white solid in a yield of 94%
1
(71 mg, 207 µmol). H NMR (500 MHz, CDCl3) δ 7.99 (s,
1H), 7.86 – 7.81 (m, 2H), 7.44 – 7.38 (m, 2H), 7.36 (d, J =
8.2 Hz, 2H), 7.28 (d, J = 16.2 Hz, 1H), 7.23 (s, 1H), 7.05 –
6.98 (m, 2H), 6.78 (d, J = 16.0 Hz, 1H), 2.43 (s, 3H). 13C
NMR (126 MHz, CDCl3) δ 162.46 (d, J = 247.6 Hz), 146.39,
142.61, 136.96, 134.89, 132.97 (d, J = 3.5 Hz), 130.48,
129.28, 128.06 (d, J = 7.8 Hz), 127.36, 117.99 (d, J = 2.0
[M+H] calcd for C19H19N2O3S 355.11164; found 355.11197. Hz), 115.65 (d, J = 21.6 Hz), 113.93, 21.74. HRMS (ESI)
m/z: [M+H] calcd for C18H16FN2O2S 343.09165; found
343.09199.
(E)-2-(2-(1-tosyl-1H-imidazol-4-yl)vinyl)benzonitrile
[NEW] (3o). The title compound was synthesized according
to the general procedure B using the following conditions
and quantities: (2-methoxyphenyl)boronic acid (65 mg).
(E)-4-(3-nitrostyryl)-1-tosyl-1H-imidazole [NEW] (3t).
The title compound was synthesized according to the
10
This article is protected by copyright. All rights reserved.