Month 2015
Synthesis of 2-Arylbenzothiazoles by Copper-Catalyzed One-Pot Three-Component
Reactions in Water
5-Fluoro-2-phenylbenzothiazole [6a] (n). Purified by flash
chromatography (petroleum ether/ethyl acetate 100:1), white
solid. 1H NMR (400 MHz, CDCl3): 8.08–8.11 (m, 2H), 7.79
(m, 2H), 7.53 (m, 3H), 7.15–7.20 (m, 1H); 13C NMR
(100 MHz, CDCl3): 170.55, 163.15, 160.73, 155.10, 154.98,
133.36, 131.29, 130.44, 129.10, 127.54, 122.33, 122.23,
114.00, 113.75, 109.48, and 109.24; MS (EI, m/z): 229 [M+].
6-Fluoro-2-phenylbenzothiazole [6a] (o). Purified by flash
chromatography (petroleum ether/ethyl acetate 100:1), white
solid. 1H NMR (400 MHz, CDCl3): 8.02–8.09 (m, 3H), 7.59–
7.62 (dd, J = 8.1, 2.4 Hz, 1H), 7.51–7.53 (m, 3H), 7.23–7.29 (m,
1H). 13C NMR (100 MHz, CDCl3): 167.82, 161.71, 159.27,
150.77, 136.09, 133.35, 131.07, 129.10, 127.45, 124.18, 124.09,
115.10, 114.86, 108.00, and 107.73; MS (EI, m/z): 229 [M+].
6-Chloro-2-phenylbenzothiazole [2g] (p). Purified by flash
chromatography (petroleum ether/ethyl acetate 100:1), white
H.-F.; Wu, W.-Q.; Zeng, W.; Wu, X.; Org Lett 2013, 15, 1598; (g)
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1
solid. H NMR (400 MHz, CDCl3): 8.01–8.11 (m, 2H), 7.98 (d,
J = 8.8 Hz, 1H), 7.90 (s, 1H), 7.46–7.53 (m, 4H); 13C NMR
(100 MHz, CDCl3): 168.56, 152.68, 136.22, 133.21, 131.27,
131.07, 129.11, 127.55, 127.15, 123.94, and 121.25; MS (EI,
m/z): 245.5 [M+].
5-Fluoro-2-(3,4-dimethoxyphenyl)benzothiazole [6a] (q). Purified
by flash chromatography (petroleum ether/ethyl acetate 100:1), white
1
solid. H NMR (400 MHz, CDCl3): 7.80 (dd, J= 8.8, 5.1 Hz, 1H),
7.75–7.69 (m, 2H), 7.60 (dd, J= 8.4, 1.9 Hz, 1H), 7.15 (d,
J= 2.4 Hz, 1H), 6.96 (d, J= 8.4 Hz, 1H), 4.04 (s, 3H), 3.98 (s, 3H);
13C NMR (100 MHz, CDCl3): 170.39, 163.14, 160.72, 155.11,
151.81, 149.36, 130.25, 126.39, 122.15, 122.05, 121.19, 113.57,
113.32, 111.01, 109.71, 109.12, 108.89, 56.14, and 56.07; MS (EI,
m/z): 289 [M+].
Acknowledgments. We are grateful to the Natural Science
Foundation of China (nos. 21072132, 21272161, 21372163),
and the Ministry of Education of China (no. 20120181110050)
for financial support.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet