The Journal of Organic Chemistry
Page 8 of 13
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0.55 (petroleum ether/ ethyl acetate, 12/1); 1H NMR (400MHz, CDCl3): δ 2.41 (s, 3H), 7.28 (d, J = 8.0 Hz, 2H), 7.36 (t, J = 7.6 Hz, 1H), 7.48 (t, J
= 7.6 Hz, 1H), 7.88 (d, J = 7.6 Hz, 1H), 7.97 (t, J = 8.4 Hz, 2H), 8.05 (d, J = 8.4 Hz, 1H); 13C NMR(100MHz, CDCl3): δ 21.5, 121.5, 123.0, 125.0,
126.2, 127.4 (2C), 129.7 (2C), 130.9, 134.9, 141.4, 154.1, 168.2; FTIR (film, cm-1): 2913, 1477, 1433, 839, 757; HRMS (EI) m/z calcd for
C14H11NS: 225.0612, found 225.0606.
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2-(2-ethoxyphenyl)benzothiazole(3i)19: The product was isolated as a colorless solid in 71% yield (181 mg), m.p. = 123.5-126.1 °C, TLC Rf = 0.36
(petroleum ether/ ethyl acetate, 8/1); 1H NMR (400MHz, CDCl3): δ 1.64 (t, J = 6.8 Hz, 3H), 4.27 (q, J = 6.8 Hz, 2H), 7.02 (d, J = 8.0 Hz, 1H),
7.11 (t, J = 7.6 Hz, 1H), 7.36 (t, J = 7.6 Hz, 1H), 7.42 (t, J = 7.6 Hz, 1H), 7.48 (t, J = 7.6 Hz, 1H), 7.93 (d, J = 8.4 Hz, 1H), 8.08 (d, J = 8.4 Hz,
1H), 8.55 (d, J = 7.6 Hz, 1H); 13C NMR(100MHz, CDCl3): δ 14.9, 64.9, 112.2, 120.9, 121.2, 122.2, 122.7, 124.5, 125.8, 129.4, 131.7, 136.1,
152.0, 156.6, 163.2; MS (m/z) 255 (M+).
2-(2,4-dimethoxyphenyl)benzothiazole(3j)20: The product was isolated as a colorless solid in 60% yield (162 mg), m.p. = 125.6-127.3 °C, TLC Rf
= 0.35 (petroleum ether/ ethyl acetate, 4/1); 1H NMR (400MHz, CDCl3): δ 3.87 (s, 3H), 4.01 (s, 3H), 6.56 (s, 1H), 6.66 (d, J = 8.8 Hz, 1H), 7.33 (t,
J = 7.2 Hz, 1H), 7.46 (t, J = 7.6 Hz, 1H), 7.89 (d, J = 7.6 Hz, 1H), 8.04 (d, J = 8.4 Hz, 1H), 8.46 (d, J = 8.8 Hz, 1H); 13C NMR(100MHz, CDCl3):
δ 55.5, 55.6, 98.4, 105.8, 115.5, 121.1, 122.2, 124.1, 125.7, 130.7, 135.6, 152.1, 158.5, 162.8, 163.3; MS (m/z) 271 (M+).
2-(2-methoxyphenyl)benzothiazole(3k)18: The product was isolated as a colorless solid in 63% yield (152 mg), m.p. = 120.2-121.8 °C, TLC Rf =
0.40 (petroleum ether/ ethyl acetate, 8/1); 1H NMR (400MHz, CDCl3): δ 4.03 (s, 3H), 7.04 (d, J = 8.4 Hz, 1H), 7.13 (t, J = 7.6 Hz, 1H), 7.36 (t, J
= 7.6 Hz, 1H), 7.44-7.48 (m, 2H), 7.92 (d, J = 8.0 Hz, 1H), 8.09 (d, J = 8.4 Hz, 1H), 8.53 (d, J = 8.0 Hz, 1H); 13C NMR(100MHz, CDCl3): δ 55.6,
111.5, 121.1, 121.2, 122.1, 122.7, 124.5, 125.8, 129.4, 131.7, 136.0, 152.0, 157.1, 163.1; FTIR (film, cm-1): 2994, 1603, 1481, 831, 757; HRMS
(EI) m/z calcd for C14H11NOS: 241.0561, found 241.0552.
2-(naphthalen-1-yl)benzothiazole(3l)18: The product was isolated as a yellow oil in 67% yield (174 mg), TLC Rf = 0.55 (petroleum ether/ ethyl
acetate, 12/1); 1H NMR (400MHz, CDCl3): δ 7.43 (t, J = 7.6 Hz, 1H), 7.52-7.57 (m, 3H), 7.61 (t, J = 7.6 Hz, 1H), 7.91 (d, J = 8.0 Hz, 2H), 7.96 (t,
J = 8.4 Hz, 2H), 8.19 (d, J = 8.0 Hz, 1H), 8.93 (d, J = 8.4 Hz, 1H); 13C NMR(100MHz, CDCl3): δ 121.3, 123.5, 124.9, 125.2, 125.8, 126.2, 126.5,
127.6, 128.4, 129.3, 130.5, 130.7, 131.0, 133.9, 135.4, 154.1, 167.6; HRMS (EI) m/z calcd for C17H11NS: 261.0612, found 261.0604.
2-(naphthalen-2-yl)benzothiazole(3m)15:The product was isolated as a colorless solid in 68% yield (177 mg), m.p. = 99.2-101.7 °C, TLC Rf = 0.56
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