General Papers
ARKIVOC 2013 (iii) 139-164
chloro-2-(2-prop-2-yn-1-yloxy)phenyl)benzoxazole (8b), 10 mg of Cu2O/C and 2.2 mL of Et3N
to give 0.22 g (75%) of 9b as a white solid. The solid residue was purified by crystallization
using (ethyl acetate/hexane). Mp. 171-172oC. IR (film) vmax/cm-1: 763, 3453, 2346, 1452, 1598,
133.2, 2920; 1H NMR (400 MHz, CDCl3) δ/ppm: 8.07 (dd, J 1.7 Hz, J 7.8 Hz, 1H), 7.74 (s, 1H),
7.47 (ddd, J 1.7 Hz, J 7.3 Hz, 1H), 7.47 (d, J 8.4 Hz, 1H), 7.39 (d, J 1.8 Hz, 1H), 7.36 (m, 3H),
7.27 (m, 3H), 7.17 (dd, J 0.7 Hz, J 8.4 Hz, 1H), 7.09 (td, J 1.0 Hz, J 7.7 Hz, 1H), 5.53 (s, 2H),
5.37 (s, 2H). 13C NMR (100 MHz, CDCl3) δ/ppm: 162.2, 157.0, 150.5, 144.9, 140.7, 134.4,
133.2, 131.3, 130.5, 129.2, 128.9, 128.2, 125.0, 122.7, 121.5, 120.4, 116.2, 113.9, 110.9, 63.8,
54.3. Anal. Calcd for C23H17ClN4O2 C, 66.27; H, 4.11; N, 13.44. Found: C, 66.25; H, 4.02; N,
13.47%.
2-[2-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl]-5-chloro-6-nitrobenzoxazole (9c). The
general procedure was followed using 0.08 g (0.61 mmol) of benzyl azide (1a), 0.20 g (0.61
mmol) of 5-chloro-6-nitro-2-(2-prop-2-ynyloxy)phenyl)benzoxazole (8c), 10 mg of Cu2O/C and
2.2 mL of Et3N to give 0.23 g (82%) of 9c as a yellow solid. The solid residue was purified by
crystallization using (ethyl acetate/hexane). Mp. 188-189oC.1H NMR (400 MHz, CDCl3) δ/ppm:
8.07 (dd, J 2.0 Hz, J 8.0 Hz, 1H), 7.89 (s, 1H), 7.67 (s, 1H), 7.60 (s, 1H), 7.5 (ddd, J 1.6 Hz, J
7.2 Hz, J 8.8 Hz, 1H), 7.34-7.31 (m, 3H), 7.23 (dd, J 2.8 Hz, J 7.6 Hz, 2H), 7.18 (d, J 7.6 Hz,
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1H), 7.07 (td, J 1.0 Hz, J 7.6 Hz, J 8.4 Hz, 1H), 5.50 (s, 1H), 5.33 (s, 1H). C NMR (100 MHz,
CDCl3) δ/ppm: 166.5, 157.6, 147.7, 145.8, 144.4, 134.5, 134.3, 131.7, 129.3, 129.1, 128.2,
123.4, 122.6, 122.0, 121.6, 114.9, 113.9, 108.4, 63.6, 54.4. Anal. Calcd for C23H16ClN5O4; C,
59.81; H, 3.49; N, 15.16. Found: C, 59.58; H, 3.29; N, 14.88%.
2-[2-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]-5-bromophenyl]-5-methylbenzoxazole (9d).
The general procedure was followed using 0.079 g (0.58 mmol) of benzyl azide (1a), 0.20 g
(0.58 mmol) of 2-(5-bromo-2-(prop-2-ynyloxy)phenyl)-5-methylbenzoxazole (8d), 10 mg of
Cu2O/C and 2.2 mL of Et3N to give 0.22 g (80%) of 9d as a white solid The solid residue was
purified by flash chromatography using (ethyl acetate/hexane). Mp. 193-195oC. IR (film)
1
vmax/cm-1: 757, 3440, 2345, 1594, 1592, 1033, 2919.3. H NMR (400 MHz, CDCl3) δ/ppm: 8.16
(s, 1H), 7.71 (s, 1H), 7.46 (d, J 8 Hz, 1H), 7.34-7.30 (m, 4H), 7.14-7.21 (m, 3H), 7.05 (d, J 8 Hz,
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1H), 7.01 (d, J 8 Hz, 1H), 5.46 (s, 2H), 5.29 (s, 2H), 2.41 (s, 3H). C NMR (100 MHz, CDCl3)
δ/ppm: 160.0, 155.8, 148.5, 144.5, 141.9, 135.1, 134.4, 134.3, 133.5, 129.2, 128.8, 128.1, 126.5,
122.8, 119.9, 118.6, 115.8, 113.7, 109.7, 64.0, 54.31, 21.5. Anal. Calcd for C24H19BrN4O2; C,
60.64; H, 4.04; N, 11.79. Found: C, 60.66; H, 3.64; N, 11.56%.
2-[2-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyloxy]-5-bromophenyl]benzoxazole (9e). The
general procedure was followed using 0.09 g (0.66 mmol) of benzyl azide (1a), 0.200 g (0.61
mmol) of 2-(5-bromo-2-(prop-2-yn-1-yloxy)phenyl)benzoxazole (8e), 10 mg of Cu2O/C and 2.2
mL of Et3N to give 0.25 g (89%) of 9e as a white solid. The solid residue was purified by
crystallization using (ethyl acetate/hexane). Mp. 179-180oC. IR (film) vmax/cm-1: IR (film)
1
vmax/cm-1: 739, 3440, 2341, 1541, 1613, 1033, 2926; H NMR (400 MHz, CDCl3) δ/ppm: 8.18
(d, J 2.0 Hz, 1H), 7.70 (s, 1H), 7.56 (ddd, J 0.6 Hz, J 3.0 Hz, J 7.5 Hz, 1H), 7.48 (dd, J 2.5 Hz, J
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8.8 Hz, 1H), 7.27 (m, 6H), 7.20 (m, 2H), 7.03 (d, J 8.9 Hz, 1H), 5.46 (s, 2H), 5.30 (s, 2H). C
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