The Journal of Organic Chemistry
NOTE
7.23 (s, 1H), 7.54À7.57 (m, 3H), 8.24 (d, J = 8.7 Hz, 2H). 13C NMR
(75 MHz, CDCl3): δ 146.8, 140.9, 136.3, 131.3, 130.3, 128.2, 124.1, 33.0.
5-(4-Methoxyphenyl)-1-methyl-1H-imidazole (3g).14b Pale
yellow solid. Mp: 106À108 °C. 1H NMR (300 MHz, CDCl3): δ 3.64
(s, 3H), 3.86 (s, 3H), 6.98 (d, J = 9 Hz, 2H), 7.05 (s, 1H), 7.33 (d, J =
9 Hz, 2H), 7.52 (br s, 1H). 13C NMR (75 MHz, CDCl3): δ 159.5, 138.5,
133.2, 130.0, 127.4, 122.1, 114.2, 55.3, 32.4.
8.36 (d, J = 8.4 Hz, 2H), 10.05 (s, 1H). 13C NMR (75 MHz, CDCl3): δ
191.3, 161.5, 150.8, 141.9, 137.9, 132.1, 130.0, 128.0, 125.9, 124.9,
120.4, 110.8.
2-(Benzo[b]thiophene-2-yl)pyridine (5a).25. White solid. Mp:
126 °C. 1H NMR (300 MHz, CDCl3): δ 7.18À7.22 (m, 1H), 7.35À7.40
(m, 2H), 7.71 (td, J = 7.5, 1.5 Hz, 1H), 7.78À7.90 (m, 4H), 8.65
(d, J = 4.8 Hz, 1H). 13C NMR (75 MHz, CDCl3): δ 152.5, 149.7, 144.8,
140.7, 140.5, 136.6, 125.1, 124.5, 124.1, 122.6, 121.1, 119.6.
3-(Benzo[b]thiophene-2-yl)quinoline (5b). Pale yellow solid.
Mp: 173À174 °C. 1H NMR (300 MHz, CDCl3): δ 7.35À7.43 (m, 2H),
7.56À7.61 (m, 1H), 7.70À7.75 (m, 2H), 7.82À7.89 (m, 3H), 8.14 (d,
J = 8.4 Hz, 1H), 8.34 (s, 1H), 9.31 (d, J = 1.2 Hz, 1H). 13C NMR (75
MHz, CDCl3): δ 148.5, 147.6, 140.6, 140.5, 139.7, 132.4, 129.7, 129.3,
128.0, 127.8, 127.5, 127.4, 124.9, 124.9, 123.9, 122.3, 120.9. HRMS
(EI+): m/z calcd for C17H11NS M+ 261.0612, found 261.0616.
3-(1-Methyl-1H-imidazol-5-yl)quinoline (5c). Pale yellow oil.
1H NMR (300 MHz, CDCl3): δ 3.74 (s, 3H), 7.26 (d, J = 0.9 Hz, 1H),
7.56À7.61 (m, 2H), 7.71À7.77 (m, 1H), 7.84 (dd, J = 5.1, 1.2 Hz, 1H),
8.11À8.14 (m, 2H), 8.96 (d, J = 2.1 Hz, 1H). 13C NMR (75 MHz,
CDCl3): δ 150.0, 147.3, 139.9, 134.4, 130.2, 129.9, 129.4, 129.3, 127.8,
127.6, 127.4, 123.1, 32.7. HRMS (EI+): m/z calcd for C13H11N3 M+
209.0953, found 209.0951.
5-(6-Methoxynaphthalen-2-yl)-1-methyl-1H-imidazole
(3h).14b White solid. Mp: 157À159 °C. 1H NMR (300 MHz, CDCl3):
δ 3.72 (s, 3H), 3.95 (s, 3H), 7.17À7.24 (m, 3H), 7.47 (dd, J = 8.4, 1.5 Hz,
1H), 7.56 (s, 1H), 7.75À7.81 (m, 3H). 13C NMR (75 MHz, CDCl3):
δ 158.1, 139.0, 133.9, 133.6, 129.5, 128.8, 128.1, 127.2, 126.9, 124.9, 119.5,
105.7, 55.4, 32.6.
1,2-Dimethyl-5-(4-nitrophenyl)-1H-imidazole (3i).20 Yellow
solid. Mp: 150À151 °C. 1H NMR (300 MHz, CDCl3): δ 2.48 (s, 3H),
3.68 (s, 3H), 7.12 (s, 1H), 7.53 (d, J = 8.7 Hz, 2H), 8.28 (d, J = 9 Hz, 2H).
13C NMR (75 MHz, CDCl3): δ 148.1, 146.6, 137.0, 131.6, 128.4, 128.2,
124.2, 31.9, 13.9.
5-(4-Methoxyphenyl)-1,2-dimethyl-1H-imidazole (3j).20
1
Pale yellow solid. Mp: 112À113 °C. H NMR (300 MHz, CDCl3):
δ 2.36 (s, 3H), 3.41 (s, 3H), 3.76 (s, 3H), 6.90 (d, J = 9 Hz, 2H), 7.21
(d, J = 9 Hz, 2H). 13C NMR (75 MHz, CDCl3): δ 159.2, 145.4, 133.2,
130.0, 125.3, 122.9, 114.0, 55.3, 31.1, 13.7.
4-(1-Methyl-1H-imidazol-5-yl)-1-phenyl-1H-pyrazole (5d).
Yellow oil. H NMR (300 MHz, CDCl3): δ 3.58 (s, 3H), 7.30 (d,
2-(5-Methylthiophene-2-yl)benzonitrile (3k).21 Pale yellow
oil. 1H NMR (300 MHz, CDCl3): δ 2.54 (d, J = 0.9 Hz, 3H), 6.81 (dd,
J = 3.6, 0.9 Hz, 1H), 7.30À7.36 (m, 1H), 7.47 (d, J = 3.6 Hz, 1H),
7.55À7.57 (m, 2H), 7.70 (d, J = 7.5 Hz, 1H). 13C NMR (75 MHz,
CDCl3): δ 142.3, 137.8, 137.0, 134.3, 132.9, 129.2, 127.7, 127.0, 126.6,
119.1, 109.4, 15.4.
1
J = 0.9 Hz, 1H), 7.21 (t, J = 7.5 Hz, 1H), 7.34À7.39 (m, 3H), 7.61 (d, J =
7.5 Hz, 2H), 7.69 (s, 1H), 7.90 (s, 1H). 13C NMR (75 MHz, CDCl3):
δ 155.1, 153.1, 147.6, 147.5, 130.7, 129.8, 129.4, 128.9, 128.2, 127.7,
127.3, 125.0, 123.7, 123.3, 121.2, 111.3, 103.0. HRMS (EI+): m/z calcd
for C13H12N4 M+ 224.1062, found 224.1068.
2-Methyl-5-(3-methylphenyl)thiophene (3l).22 Pale yellow
oil. 1H NMR (300 MHz, CDCl3): δ 2.46 (s, 3H), 2.58 (s, 3H), 6.79À
6.80 (m, 1H), 7.13À7.18 (m, 2H), 7.32 (t, J = 7.5 Hz, 1H), 7.44À7.46
(m, 2H). 13C NMR (75 MHz, CDCl3): δ 142.2, 139.3, 138.4, 134.7,
128.8, 127.9, 126.3, 126.2, 122.9, 122.7, 21.5, 15.5.
1-Methyl-5-(thiophene-2-yl)-1H-imidazole (5e). Brown oil.
1H NMR (300 MHz, CDCl3): δ 3.71 (s, 3H), 7.08À7.12 (m, 2H), 7.18
(d, J = 1.2 Hz, 1H), 7.36 (dd, J = 4.8, 1.5 Hz, 1H), 7.51 (s, 1H). 13C NMR
(75 MHz, CDCl3): δ 139.2, 130.6, 129.2, 127.9, 127.6, 126.2, 125.9,
32.6. HRMS (EI+): m/z calcd for C8H8N2S M+ 164.0408, found
164.0401.
2-Methyl-5-(4-nitrophenyl)thiophene (3m).22 Yellow solid.
Mp: 130À131 °C. 1H NMR (300 MHz, CDCl3): δ 2.55 (d, J = 0.9 Hz,
3H), 6.81 (dd, J = 3.6, 1.2 Hz, 1H), 7.29 (d, J = 3.6 Hz, 1H), 7.65 (d, J =
9 Hz, 2H), 8.20 (d, J = 9 Hz, 2H). 13C NMR (75 MHz, CDCl3): δ 146.2,
143.0, 140.8, 139.1, 127.0, 125.8, 125.3, 124.4, 15.6.
1,2-Dimethyl-5-(thiophene-2-yl)-1H-imidazole (5f).26 Yel-
1
low oil. H NMR (300 MHz, CDCl3): δ 2.35 (s, 3H), 3.48 (s, 3H),
6.94À6.95 (m, 2H), 6.99À7.02 (m, 1H), 7.25 (dd, J = 8.1, 1.2 Hz, 1H).
13C NMR (75 MHz, CDCl3): δ 146.3, 131.5, 127.5, 127.3, 126.4, 126.3,
125.8, 31.2, 13.7.
5-(4-Methoxyphenyl)-4-methylthiazole (3n).7 Yellow oil. 1H
NMR (300 MHz, CDCl3): δ 2.51 (s, 3H), 3.83 (s, 3H), 6.95 (d, J = 8.7 Hz,
2H), 7.36 (d, J = 8.7 Hz, 1H), 8.63 (s, 1H). 13C NMR (75 MHz, CDCl3):
δ 159.4, 149.7, 147.9, 131.7, 130.5, 124.2, 114.2, 55.3, 16.0.
4-(1,2-Dimethyl-1H-imidazol-5-yl)-1-phenyl-1H-pyrazole
(5g). Yellow oil. H NMR (300 MHz, CDCl3): δ 2.34 (s, 3H), 3.46
1
(s, 3H), 6.89 (s, 1H), 7.35À7.41 (m, 3H), 7.61À7.64 (m, 2H), 7.67
(s, 1H), 7.88 (s, 1H), 8.14 (d, J = 8.4 Hz, 1H), 8.34 (s, 1H), 9.31 (d, J =
1.2 Hz, 1H). 13C NMR (75 MHz, CDCl3): δ 145.7, 140.1, 139.8, 129.5,
126.8, 126.0, 125.9, 124.9, 119.1, 113.4, 31.1, 13.7. HRMS (EI+): m/z
calcd for C14H14N4 M+ 238.1218, found 238.1228.
4-(4-Methylthiazol-5-yl)benzaldehyde (3o). Yellow oil. 1H
NMR (300 MHz, CDCl3): δ 2.52 (s, 3H), 7.56 (d, J = 8.4 Hz, 2H), 7.87
(d, J = 8.1 Hz, 2H), 8.70 (s, 1H), 7.63 (d, J = 8.4 Hz, 2H), 9.98 (s, 1H).
13C NMR (75 MHz, CDCl3): δ 191.4, 151.4, 149.8, 138.1, 135.3, 130.0,
129.6, 126.7, 16.4. HRMS (EI+): m/z calcd for C12H10O2 M+ 186.0681,
found 186.0672.
2-(1,2-Dimethyl-1H-imidazol-5-yl)pyridine (5h).27 Yellow
1
oil. H NMR (300 MHz, CDCl3): δ 2.47 (s, 3H), 3.91 (s, 3H), 7.15
4-(Thiophene-2-yl)benzaldehyde (3p).23 White solid. Mp:
73À74 °C. 1H NMR (300 MHz, CDCl3): δ 7.02 (dd, J = 5.1, 3.9 Hz,
1H), 7.28 (dd, J = 5.1, 1.2 Hz, 1H), 7.34 (dd, J = 3.6, 1.2 Hz, 1H), 7.63
(d, J = 8.4 Hz, 2H), 7.76 (d, J = 8.4 Hz, 2H), 9.88 (s, 1H). 13C NMR
(75 MHz, CDCl3): δ 191.4, 142.7, 140.1, 135.1, 130.5, 128.5, 126.9,
126.0, 125.1.
(ddd, J = 7.5, 4.8, 1.2 Hz, 1H), 7.31 (s, 1H), 7.52 (dt, J = 8.1, 0.9 Hz, 1H),
7.69 (td, J = 7.8, 1.8, 1H), 8.58À8.61 (m, 1H). 13C NMR (75 MHz,
CDCl3): δ 150.6, 148.9, 147.8, 136.6, 131.8, 127.9, 121.8, 121.3, 31.9, 13.4.
3-(5-Methylthiophene-2-yl)quinoline (5i).28 Pale yellow
solid. Mp: 124À125 °C. 1H NMR (300 MHz, CDCl3): δ 2.46 (d, J =
0.9 Hz, 3H), 6.71 (dd, J = 3.6, 1.2 Hz, 1H), 7.20 (d, J = 3.6 Hz, 1H), 7.44
(td, J = 6.9, 1.2 Hz, 1H), 7.57À7.63 (m, 1H), 7.67À7.70 (m, 1H),
8.05À8.07 (m, 2H), 9.11 (d, J = 2.4 Hz, 1H). 13C NMR (75 MHz,
CDCl3): δ 148.3, 147.0, 140.9, 138.2, 130.4, 129.2, 128.9, 128.0, 127.8,
127.7, 127.1, 126.6, 124.3, 15.5. HRMS (EI+): m/z calcd for C10H8ClNS
M+ 209.0066, found 209.0072.
3-(5-Methylfuran-2-yl)benzaldehyde (3q). Brown oil. 1H
NMR (300 MHz, CDCl3): δ 2.27 (s, 3H), 5.97À5.98 (m, 1H), 6.52
(d, J = 3.3 Hz, 1H), 7.39 (t, J = 4.8 Hz, 1H), 7.59 (dt, J = 7.5, 1.5 Hz, 1H),
7.74 (dt, J = 7.8, 1.8 Hz, 1H), 7.99 (t, J = 1.5 Hz, 1H), 9.91 (s, 1H).
13C NMR (75 MHz, CDCl3): δ 192.3, 152.8, 150.8, 136.8, 132.1, 129.3,
128.8, 127.7, 124.2, 108.0, 107.3, 13.7.
2-Chloro-5-(5-methylthiophene-2-yl)pyridine (5j). Pale yel-
low solid. Mp: 94À95 °C. 1H NMR (300 MHz, CDCl3): δ 2.50 (d, J =
0.9 Hz, 3H), 6.74 (dd, J = 3.6, 0.9 Hz, 1H), 7.11 (d, J = 3.6 Hz, 1H), 7.26
(dd, J = 8.4, 0.6 Hz, 1H), 7.71 (dd, J = 8.4, 2.7 Hz, 1H), 8.53 (d, J =
4-(Benzo[d]thiazol-2-yl)benzaldehyde (3r).24 Yellow solid.
1
Mp: 132À133 °C. H NMR (300 MHz, CDCl3): δ 7.35À7.39 (m,
2H), 7.56À7.59 (m, 1H), 7.76À7.79 (m, 1H), 7.97 (d, J = 8.7 Hz, 2H),
8141
dx.doi.org/10.1021/jo201516v |J. Org. Chem. 2011, 76, 8138–8142