Medicinal Chemistry Research
1H NMR (300 MHz, CDCl3): δ 2.49 (s, 3H), 3.85 (s, 6H),
3.91 (s, 6H), 3.92 (s, 3H), 3.94 (s, 3H), 6.53 (s, 2H), 6.63 (s,
2H), 7.10 (d, 1H, J = 8.14 Hz), 7.19 (d, 1H, J = 8.14 Hz),
7.38 (t, 1H), 7.56 (s, 1H); 13C NMR (75 MHz, CDCl3): δ
19.4, 57.4, 61.5, 114.6, 119.5, 120.5, 123.5, 125.5, 127.6,
138.4, 139.5, 140.5, 140.8, 148.5, 153.5, 157.8, 160.6; MS
(ESI): 492 [M+H]+. Anal. Calcd for C28H29NO7: C, 68.42;
H, 5.95; N, 2.85; Found: C, 68.45; H, 5.97; N, 2.81.
eq) with 2-amino-4-bromophenol 10i, (1.2 mmol, 226 mg,
1.0 eq), Pb(OAc)4 (6 mmol, 266 mg, 5.0 eq) and the crude
product was purified by column chromatography (ethyl
acetate:hexane, 1:1) to afford pure 11i, (456 mg, 64%).
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Mp: 252–254 °C, H NMR (300 MHz, CDCl3): δ 3.82 (s,
6H), 3.85 (s, 6H), 3.91 (s, 3H), 3.93 (s, 3H), 6.54 (s, 2H),
6.63 (s, 2H), 7.32 (d, 1H, J = 7.29 Hz), 7.39 (d, 1H, J =
7.29 Hz), 7.52 (s, 1H), 7.69 (s, 1H); 13C NMR (75 MHz,
CDCl3): δ 56.4, 58.6, 60.4, 62.7, 110.6, 113.4, 114.8,
120.6, 128.5, 129.6, 138.4, 139.7, 140.7, 143.4, 146.5,
146.7, 153.4, 157.4, 160.7; MS (ESI): 557 [M+H]+.
Anal. Calcd for C27H26BrNO7: C, 58.28; H, 4.71; N, 2.52;
Found: C, 58.28; H, 4.69; N, 2.61.
2-(2,2-Bis(3,4,5-trimethoxyphenyl)vinyl)-5-
methoxybenzoxazole (11g)
Compound 11g was prepared by following the method
described for 11a, employing 9 (1.2 mmol, 500 mg, 1.0 eq)
with 2-amino-4-methoxyphenol 10g (1.2 mmol, 167 mg, 1.0
eq), Pb(OAc)4 (6 mmol, 266 mg, 5.0 eq) and the crude product
was purified by column chromatography (ethyl acetate:hexane,
1:1) to afford pure 11g, (436 mg, 67%). Mp: 244–246 °C, 1H
NMR (300 MHz, CDCl3): δ 3.76 (s, 3H), 3.82 (s, 6H), 3.85 (s,
6H), 3.91 (s, 3H), 3.93 (s, 3H), 6.54 (s, 2H), 6.63 (s, 2H), 6.76
(s, 1H), 7.09 (d, 1H, J = 7.24 Hz), 7.32 (d, 1H, J = 7.24 Hz),
7.51 (s, 1H); 13C NMR (75 MHz, CDCl3): δ 54.7, 56.4, 58.6,
60.4, 62.7, 104.6, 106.5, 109.7, 114.5, 120.6, 138.4, 139.6,
140.5, 144.5, 146.4, 153.4, 155.3, 157.3, 159.7; MS (ESI):
508 [M+H]+. Anal. Calcd for C28H29NO8: C, 66.26; H, 5.76;
N, 2.76; Found: C, 66.38; H, 5.74; N, 2.69.
2-(2,2-Bis(3,4,5-trimethoxyphenyl)vinyl)-6-
bromobenzoxazole (11j)
Compound 11j was prepared by following the method
described for the preparation of the 11a, employing 9
(1.2 mmol, 500 mg, 1.0 eq) with 2-amino-5-bromophenol
10j (1.2 mmol, 226 mg, 1.0 eq), Pb(OAc)4 (6 mmol,
266 mg, 5.0 eq) and the crude product was purified by
column chromatography (ethyl acetate:hexane, 1:1) to
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afford pure 11j (461 mg, 64%). Mp: 253–255 °C, H NMR
(300 MHz, CDCl3): δ 3.82 (s, 6H), 3.85 (s, 6H), 3.91 (s,
3H), 3.93 (s, 3H), 6.54 (s, 2H), 6.63 (s, 2H), 7.35 (d, 1H,
J = 7.28 Hz), 7.52 (s, 1H), 7.61–7.65 (m, 2H); 13C NMR
(75 MHz, CDCl3): δ 56.4, 58.6, 60.4, 62.7, 112.4, 114.6,
119.6, 120.6, 122.4, 128.5, 138.5, 139.5, 140.8, 142.3,
152.6, 153.8, 157.8, 160.8; MS (ESI): 557 [M+H]+. Anal.
Calcd for C27H26BrNO7: C, 58.28; H, 4.71; N, 2.52; Found:
C, 58.3; H, 4.72; N, 2.51.
2-(2,2-Bis(3,4,5-trimethoxyphenyl)vinyl)-6-
methoxybenzoxazole (11h)
Compound 11h was prepared by following the method
described for 11a, employing 9 (1.2 mmol, 500 mg, 1.0
eq) with 2-amino-5-methoxyphenol hydrogen chloride
10h (1.2 mmol, 211 mg, 1.0 eq), Pb(OAc)4 (6 mmol,
266 mg, 5.0 eq) and the crude product was purified by
column chromatography (ethyl acetate:hexane, 1:1) to
afford pure 11h (440 mg, 67%). Mp: 243–245 °C, 1H
NMR (300 MHz, CDCl3): δ 3.77 (s, 3H), 3.82 (s, 6H),
3.85 (s, 6H), 3.91 (s, 3H), 3.93 (s, 3H), 6.54 (s, 2H), 6.63
(s, 2H), 6.78 (s, 1H), 7.10 (d, 1H, J = 7.24 Hz), 7.31 (d,
1H, J = 7.24 Hz), 7.51 (s, 1H); 13C NMR (75 MHz,
CDCl3): δ 54.7, 56.4, 58.6, 60.4, 62.7, 96.6, 112.4, 114.5,
120.5, 121.6, 136.5, 138.6, 139.6, 140.6, 153.4, 153.8,
157.8, 158.6, 160.4; MS (ESI): 508 [MH]+. Anal. Calcd
for C28H29NO8: C, 66.26; H, 5.76; N, 2.76; Found: C,
66.18; H, 5.84; N, 2.74.
2-(2,2-Bis(3,4,5-trimethoxyphenyl)vinyl)-6-
chlorobenzoxazole (11k)
Compound 11k was prepared by following the method
described for the preparation of the 11a, employing 9
(1.2 mmol, 500 mg, 1.0 eq) with 2-amino-5-chlorophenol
10k (1.2 mmol, 172 mg, 1.0 eq), Pb(OAc)4 (6 mmol,
266 mg, 5.0 eq) and the crude product was purified by
column chromatography (ethyl acetate:hexane, 1:1) to
afford pure 11k, (466 mg, 71%). Mp: 235–237 °C, 1H
NMR (300 MHz, CDCl3): δ 3.82 (s, 6H), 3.85 (s, 6H),
3.91 (s, 3H), 3.93 (s, 3H), 6.54 (s, 2H), 6.63 (s, 2H), 7.23
(d, 1H, J = 7.26 Hz), 7.40 (d, 1H, J = 7.26 Hz), 7.54 (s,
1H), 7.60 (s, 1H); 13C NMR (75 MHz, CDCl3): δ 56.4,
58.6, 60.4, 62.7, 110.6, 114.5, 119.6, 120.6, 125.6, 129.6,
138.6, 139.8, 140.6, 140.9, 146.5, 153.4, 157.6, 161.6;
MS (ESI): 512 [M+H]+. Anal. Calcd for C27H26BrNO7:
C, 63.34; H, 5.12; N, 2.74; Found: C, 63.36; H, 5.14;
N, 2.71.
2-(2,2-Bis(3,4,5-trimethoxyphenyl)vinyl)-5-
bromobenzoxazole (11i)
Compound 11i was prepared by following the method
described for 11a, employing 9 (1.2 mmol, 500 mg, 1.0