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δ = 2.42 (3H, s), 2.50 (3H, s), 7.15 (2H, dd, J = 8.2, 0.7 Hz), 7.30–7.35
(3H, m), 7.63 (1H, d, J = 8.1 Hz), 8.12 (1H, d, J = 8.2 Hz); 13C NMR
(125 MHz, in CDCl3): δ 21.6, 21.8, 110.7, 119.2, 124.6, 125.7, 127.4,
129.6, 135.3, 140.0, 141.7, 151.0, 162.8 ppm. m/z (MS): 224
[M+H]+.
6-Nitro-2-phenylbenzo[d]oxazole (3ac): Yellow solid, m.p. 237.5–
238.7 °C. 1H NMR (500 MHz, in CDCl3): δ = 7.55–7.65 (3H, m), 7.84
(1H, d, J = 8.8 Hz), 8.28–8.34 (3H, m), 8.49 (1H, d, J = 2.0 Hz); 13
C
NMR (125 MHz, in CDCl3): δ 107.2. 119.8, 120.8, 126.0, 128.3,
129.2, 132.9, 145.2, 147.4, 149.9, 167.4 ppm. m/z (MS): 241 [M+H]+.
Anal. Calcd for C13H8N2O3: C, 65.00; H, 3.36; N, 11.66. Found: C,
65.16; H, 3.19. N, 11.50%.
6-Nitro-2-p-tolylbenzo[d]oxazole (3ec): Yellow solid, m.p. 160.2–
161.9 °C. 1H NMR (500 MHz, in CDCl3): δ = 2.47 (3H, s), 7.36 (2H,
d, J = 8.0 Hz), 7.80 (2H, d, J = 8.8 Hz), 8.15 (2H, d, J = 8.2 Hz), 8.30
(1H, dd, J = 8.8, 2.1 Hz), 8.45 (1H, d, J = 2.1); 13C NMR (125 MHz,
in CDCl3): δ 21.8, 107.1, 119.5, 120.8, 123.2, 128.2, 129.9, 143.8,
145.0, 147.6, 149.8, 167.7 ppm. m/z (MS): 255 [M+H]+. Anal. Calcd
for C14H10N2O3: C, 66.14; H, 3.96; N, 11.02. Found: C, 65.97; H, 4.12;
N, 11.14%.
2-(4-Bromophenyl)-6-nitrobenzo[d]oxazole (3lc): White solid,
m.p. 175.8–177.3 °C. 1H NMR (500 MHz, in CDCl3): δ = 7.71–7.74
(2H, m), 7.86 (2H, d, J = 8.8 Hz), 8.14–8.17 (2H, m), 8.34 (1H, dd,
J = 8.8, 2.1 Hz), 8.50 (1H, d, J = 2.0 Hz); 13C NMR (125 MHz, in
CDCl3): δ 107.3, 120.0, 121.0, 124.9, 127.9, 129.6, 132.6, 145.4,
147.3, 149.9, 166.5 ppm. m/z (MS): 319, 321 [M+H]+. Anal. Calcd for
C13H7BrN2O3: C, 48.93; H, 2.21; N, 8.78. Found: C, 48.75; H, 2.36; N,
8.90%.
9
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This study was supported by 973 projects (2011CB512005),
the projects of Key Laboratory for the Chemistry and Molecu-
lar Engineering of Medicinal Resources (Guangxi Normal
University), Ministry of Education of China (CMEMR2011-
15), and Guangxi Natural Science Foundation of China
(2011GXNSFD018010 and 2010GXNSFF013001).
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Electronic Supplementary Information
1
Copies of H and 13C NMR spectra of new compounds have
been deposited in the ESI available through stl.publisher.
ingentaconnect.com/content/stl/jcr/supp-data.
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Received 22 February 2012; accepted 30 March 2012
Paper 1201179 doi: 10.3184/174751912X13360692916944
Published online: 4 June 2012
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