ACCEPTED MANUSCRIPT
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5-(6-chloropyridin-3-yl)-2-methylthiazole (3b). H NMR (400 MHz, CDCl3) δ
8.55–8.53 (m, Ar-H, 1H), 7.83 (s, Ar-H, 1H), 7.76 (dd, J = 8.3, 2.6 Hz, Ar-H, 1H),
7.36 (dd, J = 8.3, 0.6 Hz, Ar-H, 1H), 2.75 (s, Ar-CH3, 3H).13C NMR (101 MHz,
CDCl3) δ 166.9, 150.6, 147.0, 139.1, 136.2, 133.6, 126.8, 124.5, 19.5.
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5-(6-fluoropyridin-3-yl)-2-methylthiazole (4b). H NMR (400 MHz, CDCl3) δ 8.32
(dd, J = 1.7, 0.8 Hz, Ar-H, 1H), 7.86 (ddd, J = 8.5, 7.4, 2.6 Hz, Ar-H, 1H), 7.74 (s,
Ar-H, 1H), 6.94 (ddd, J = 8.5, 3.1, 0.6 Hz, Ar-H, 1H), 2.70 (s, Ar-CH3, 3H). 13C NMR
(101 MHz, CDCl3) δ 166.4, 164.1, 161.8, 145.1, 145.0, 139.0, 138.9, 138.7, 138.7,
133.5, 125.9, 125.8, 110.0, 109.6, 19.3.
2-methyl-5-(quinolin-4-yl)thiazole (6b). 1H NMR (400 MHz, CDCl3) δ 8.89 (d, J =
4.4 Hz, Ar-H, 1H), 8.17 (dd, J = 8.4, 0.8 Hz, Ar-H, 2H), 7.85 (s, Ar-H, 1H), 7.74 (ddd,
J = 8.5, 6.9, 1.3 Hz, Ar-H, 1H), 7.56 (ddd, J = 8.2, 6.9, 1.3 Hz, Ar-H, 1H), 7.38 (d, J =
4.4 Hz, Ar-H, 1H), 2.81 (s, Ar-CH3, 3H).13C NMR (101 MHz, CDCl3) δ 167.5, 149.6,
148.5, 142.0, 137.4, 132.9, 129.9, 129.6, 127.1, 126.1, 124.8, 121.8, 19.1.
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2-methyl-5-(quinolin-3-yl)thiazole (7b). H NMR (400 MHz, CDCl3) δ 9.09 (d, J =
2.3 Hz, Ar-H, 1H), 8.18 (d, J = 2.2 Hz, Ar-H, 1H), 8.11–8.08 (m, Ar-H, 1H), 7.97 (s,
Ar-H, 1H), 7.83–7.80 (m, Ar-H, 1H), 7.70 (ddd, J = 8.4, 6.9, 1.5 Hz, Ar-H, 1H), 7.56
(ddd, J = 8.1, 6.9, 1.2 Hz, Ar-H, 1H), 2.77 (s, Ar-CH3, 3H).13C NMR (101 MHz,
CDCl3) δ 166.4, 148.6, 147.4, 138.9, 135.4, 132.4, 129.7,127.4, 129.3, 127.8, 127.4,
124.9, 19.5.
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5-(6-methoxypyridin-3-yl)-2,4-dimethylthiazole (1c). H NMR (400 MHz, CDCl3) δ
8.18 (s, Ar-H, 1H), 7.56 (d, J = 8.5 Hz, Ar-H, 1H), 6.76 (d, J = 8.5 Hz, Ar-H, 1H),
3.94 (s, Ar-OCH3, 3H), 2.66 (s, Ar-CH3, 3H), 2.39 (s, Ar-CH3, 3H).13C NMR (101
MHz, CDCl3) δ 163.4, 147.5, 146.7, 139.2, 127.6, 121.4, 110.8, 53.5, 19.1, 15.7.
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2,4-dimethyl-5-(6-methylpyridin-3-yl)thiazole (2c). H NMR (400 MHz, CDCl3) δ
8.51 (d, J = 2.0 Hz, Ar-H, 1H), 7.56 (dd, J = 8.0, 2.4 Hz, Ar-H, 1H), 7.17 (d, J = 8.0
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Hz, Ar-H, 1H), 2.66 (s, 3H), 2.56 (s, Ar-CH3, 3H), 2.41 (s, Ar-CH3, 3H). C NMR
(101 MHz, CDCl3) δ 163.9, 157.5, 148.8, 145.0, 136.5, 127.5, 125.5, 122.9, 24.1, 19.1,
15.8.
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5-(6-fluoropyridin-3-yl)-2,4-dimethylthiazole (4c). H NMR (400 MHz, CDCl3) δ
8.20 (d, J = 2.4 Hz, Ar-H, 1H), 7.76 (ddd, J = 8.4, 7.6, 2.6 Hz, Ar-H, 1H), 6.99–6.90
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(m, Ar-H, 1H), 2.65 (s, Ar-CH3, 3H), 2.37 (s, Ar-CH3, 3H). C NMR (101 MHz,
CDCl3) δ 164.3, 163.9, 161.5, 148.4, 147.4, 147.3, 141.5, 141.4, 126.4, 126.4, 126.0,
125.9, 109.6, 109.2, 19.0, 15.7.
5-(isoquinolin-4-yl)-2,4-dimethylthiazole (5c). 1H NMR (400 MHz, CDCl3) δ 9.27 (s,
Ar-H, 1H), 8.49 (s, Ar-H, 1H), 8.04 (d, J = 8.1 Hz, Ar-H, 1H), 7.83–7.57 (m, Ar-H,
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