JOURNAL OF CHEMICAL RESEARCH 2014 403
743 cm–1; 1H NMR (400 MHz, CDCl3) δ 8.15 (s, 1H), 7.84 (d, J=8.0 Hz,
1H), 7.63 (d, J=8.0 Hz, 1H), 7.58–7.55 (m, 1H), 7.50–7.46 (m, 2H),
7.36 (t, J=8.0 Hz, 1H), 7.30 (dd, J1 =8.0 Hz, J2 =2.4 Hz, 1H), 7.25 (t,
J=8.0 Hz, 1H), 7.09 (td, J1 =8.0 Hz, J2 =2.4 Hz, 1H), 7.02 (t, J=8.0 Hz,
2H); 13C NMR (CDCl3, 100 MHz) δ 164.14, 163.29, 161.64, 160.80,
143.26, 141.91, 134.32, 133.84, 133.76, 133.36, 133.26, 127.53, 127.43,
124.80, 124.17, 120.85, 120.14, 119.04, 118.80, 118.43, 118.39, 116.22,
115.97, 115.75, 111.05, 93.64, 86.55, 79.88, 71.82; HRMS (EI): [M]+
calcd for C23H12F2N2: 354.0969; found: 354.0966.
1-((4-Fluoro-2-(oct-1-yn-1-yl)phenyl)ethynyl)-1H-benzo[d]imidazole
(3n): Red oil; yield 59%; IR (neat) v 2929, 2857, 2257, 1603, 1568, 1491,
1454, 1291, 873, 743 cm–1; 1H NMR (400 MHz, CDCl3) δ 8.14 (s, 1H),
7.85 (dd, J1 =8.0 Hz, J2 =0.8 Hz, 1H), 7.71 (dd, J1 =8.0 Hz, J2 =1.6 Hz,
1H), 7.52–7.49 (m, 1H), 7.44–7.36 (m, 2H), 7.18 (dd, J1 =8.0 Hz,
J2 =2.8 Hz, 1H), 7.01 (td, J1 =8.0 Hz, J2 =2.8 Hz, 1H), 2.47 (t, J=8.0 Hz,
3H), 1.62–1.54 (m, 2H), 1.41–1.37 (m, 2H), 1.21–1.16 (m, 4H), 0.83–0.79
(m, 3H); 13C NMR (CDCl3, 100 MHz) δ 163.38, 160.89, 143.35, 141.94,
134.51, 133.40, 133.31, 128.86, 128.76, 124.70, 124.04, 120.81, 119.92,
119.90, 119.13, 118.91, 115.34, 110.96, 96.65, 79.13, 78.37, 78.35, 71.92,
31.18, 28.55, 28.52, 22.38, 19.64, 13.94; HRMS (EI): [M]+ calcd for
C23H21FN2: 344.1689; found: 344.1689.
7.58–7.45 (m, 4H), 7.39–7.33 (m, 2H), 7.22 (s, 1H), 7.13 (s, 1H), 7.22
(s, 1H), 7.06 (t, J=8.0 Hz, 2H); 13C NMR (CDCl3, 100 MHz) δ 164.00,
161.50, 133.50, 133.41, 131.91, 131.64, 129.48, 128.66, 128.20, 125.76,
119.00, 116.01, 115.79, 92.71, 87.36, 81.76, 69.58; HRMS (EI): [M]+
calcd for C19H11N2: 286.0906; found: 286.0905.
1-((4-Fluoro-2-(phenylethynyl)phenyl)ethynyl)-1H-imidazole (3u):
Red oil; yield 39%; IR (neat) v 2924, 2261, 1600, 1571, 1394, 1066, 1012,
819, 757, 691 cm–1; 1H NMR (400 MHz, CDCl3) δ 7.85 (s, 1H), 7.52–7.50
(m, 3H), 7.38–7.37 (m, 3H), 7.30–7.27 (m, 1H), 7.22 (s, 1H), 7.11 (s,
1H), 7.07 (t, J=8.0 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ 163.46,
160.97, 139.96, 133.53, 133.44, 131.62, 129.39, 129.09, 128.59, 128.13,
128.03, 122.36, 121.70, 119.92, 119.89, 118.91, 118.67, 116.06, 115.84,
94.92, 86.59 (d, J=13.2 Hz), 81.37, 68.75; HRMS (EI): [M]+ calcd for
C19H11FN2: 286.0906; found: 286.0902.
1-((2-(Oct-1-yn-1-yl)phenyl)ethynyl)-1H-imidazole (3v): Red oil; yield
53%; IR (neat) v 3117, 2929, 2858, 2262, 1594, 1473, 1310, 1170, 1065,
1
758, 649 cm–1; H NMR (400 MHz, CDCl3) δ 7.83 (s, 1H), 7.49–7.44
(m, 2H), 7.32–7.25 (m, 2H), 7.21 (s, 1H), 7.11 (s, 1H), 2.47 (t, J=6.8 Hz,
3H), 1.65–1.57 (m, 2H), 1.49–1.44 (m, 2H), 1.28–1.27 (m, 4H), 0.87 (t,
J=6.2 Hz, 3H); 13C NMR (CDCl3, 100 MHz) δ 140.01, 132.02, 131.63,
129.21, 128.58, 127.36, 126.73, 123.33, 121.74, 95.32, 80.97, 78.92,
69.70, 31.27, 28.68, 28.55, 22.47, 19.59, 14.03; HRMS (EI): [M]+ calcd
for C19H20N2: 276.1626; found: 276.1622.
5,6-Dimethyl-1-((2-(phenylethynyl)-5-(trifluoromethyl)phenyl)
ethynyl)-1H-benzo[d]imidazole (3w): White solid; yield 54%; m.p.
133–135 °C; IR (neat) v 2923, 2262, 1609, 1498, 1379, 1259, 1125, 1070,
756, 692 cm–1; 1H NMR (400 MHz, CDCl3) δ 8.06 (s, 1H), 7.84 (s, 1H),
7.72 (t, J=8.0 Hz, 1H), 7.59–7.54 (m, 4H), 7.41–7.33 (m, 4H), 2.36 (s,
3H), 2.13 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 142.57, 140.38, 134.59,
133.33, 132.56, 132.46, 131.88, 130.29, 129.96, 129.18, 128.58, 127.89,
124.96, 124.60, 122.18, 122.09, 120.85, 111.23, 96.00, 86.82, 82.08,
71.57, 20.24, 20.12; HRMS (EI): [M]+ calcd for C26H17F3N2: 414.1344;
found: 414.1345.
5,6-Dimethyl-1-((2-(phenylethynyl)phenyl)ethynyl)-1H-benzo[d]
imidazole (3o): Red oil; yield 57%; IR (neat) v 2923, 2250, 1596, 1497,
1
1464, 1162, 1159, 1047, 840, 692 cm–1; H NMR (400 MHz, CDCl3) δ
8.06 (s, 1H), 7.63–7.57 (m, 3H), 7.54–7.52 (m, 2H), 7.39–7.32 (m, 6H),
2.36 (s, 3H), 2.13 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 142.70, 140.40,
134.34, 133.06, 132.77, 132.11, 131.75, 131.22, 128.60, 128.45, 128.19,
128.15, 125.33, 124.18, 122.87, 120.71, 111.31, 93.65, 87.92, 80.77,
72.42, 20.20, 20.08; HRMS (EI): [M]+ calcd for C25H18N2: 346.1470;
found: 346.1475.
6-Nitro-1-((2-(phenylethynyl)phenyl)ethynyl)-1H-benzo[d]imidazole
(3p): Yield solid; yield 55%; IR (neat) v 2925, 2361, 1593, 1522, 1492,
1
1343, 1176, 1058, 759, 699 cm–1; H NMR (400 MHz, CDCl3) δ 8.81
(s, 1H), 8.23 (s, 1H), 8.15 (d, J=9.6 Hz, 1H), 7.74 (d, J=6.8 Hz, 1H),
7.51–7.44 (m, 2H), 7.31–7.27 (m, 3H), 7.21 (d, J=8.8 Hz, 1H), 7.14 (d,
J=6.8 Hz, 2H), 7.07 (d, J=6.8 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ
192.86, 146.43, 144.66, 144.32, 143.44, 140.07, 135.83, 134.18, 130.62,
129.92, 129.53, 128.98, 128.87, 128.15, 127.78, 124.07, 120.10, 119.76,
117.41, 112.29; HRMS (EI): [M]+ calcd for C23H13N3O2: 363.1008;
found: 363.1005.
We thank Professors Xin Lv and Zhi-Jing Wang for their help in
the organisation and discussion of the manuscript.
Received 7 March 2014; accepted 7 May 2014
Paper 1402509 doi: 10.3184/174751914X14019525018744
Published online: 12 July 2014
1-((2-(Phenylethynyl)phenyl)ethynyl)-1H-imidazole (3q): Red oil;
yield 47%; IR (neat) v 2923, 2263, 1598, 1494, 1470, 1310, 1099, 1012,
References
1
812, 691 cm–1; H NMR (400 MHz, CDCl3) δ 7.85 (s, 1H), 7.58 (d,
1
S. Saluja, R. Zou, J.C. Drach and L.B., Townsend J. Med. Chem., 1996, 39,
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J=8.0 Hz, 1H), 7.54–7.51 (m, 3H), 7.37–7.32 (m, 5H), 7.22 (s, 1H), 7.11
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128.74, 128.63, 128.54, 128.14, 125.86, 123.64, 122.83, 121.74, 93.82,
87.63, 81.72, 69.65; HRMS (EI): [M]+ calcd for C19H12N2: 268.1000;
found: 268.1000.
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4-Methyl-1-((2-(phenylethynyl)phenyl)ethynyl)-1H-imidazole (3r):
Red oil; yield 51%; IR (neat) v 2963, 2923, 2259, 1598, 1495, 1409,
1292, 1071, 757, 691 cm–1; 1H NMR (400 MHz, CDCl3) δ 7.74 (s, 1H),
7.59–7.56 (m, 1H), 7.54–7.50 (m, 3H), 7.37–7.32 (m, 5H), 6.90 (s, 1H),
2.95 (s, 3H); 13C NMR (CDCl3, 100 MHz) δ 139.41, 138.64, 131.90,
131.56, 131.46, 128.68, 128.51, 128.40, 128.11, 125.78, 123.99, 122.95,
117.73, 93.76, 87.76, 76.29, 69.05, 13.46; HRMS (EI): [M]+ calcd for
C20H11N2: 282.1157; found: 282.1154.
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1-((2-(p-Tolylethynyl)phenyl)ethynyl)-1H-imidazole
(3s):
Red
oil; yield 48%; IR (neat) v 2921, 2257, 1593, 1502, 1472, 1310, 1099,
1
1012, 815, 758 cm–1; H NMR (400 MHz, CDCl3) δ 7.84 (s, 1H), 7.57
(d, J=8.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.41 (d, J=8.0 Hz, 2H),
7.37–7.30 (m, 2H), 7.22 (s, 1H), 7.17 (d, J=8.0 Hz, 2H), 7.11 (s, 1H), 2.38
(s, 3H); 13C NMR (CDCl3, 100 MHz) δ 140.00, 138.97, 131.80, 131.45,
131.41, 129.29, 128.58, 127.93, 126.06, 123.55, 121.72, 119.73, 94.09,
87.02, 81.65, 69.69; HRMS (EI): [M]+ calcd for C20H11N2: 282.1157;
found: 282.1156.
1-((2-((4-Fluorophenyl)ethynyl)phenyl)ethynyl)-1H-imidazole (3t):
Red oil; yield 44%; IR (neat) v 2923, 2259, 1597, 1472, 1228, 1065,
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1012, 836, 758, 648 cm–1; H NMR (400 MHz, CDCl3) δ 7.85 (s, 1H),
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