Organic & Biomolecular Chemistry
Paper
Flash chromatography (hexane/EtOAc/CH2Cl2 = 5 : 1 : 2) on (26.9 mg, 0.1 mmol). Flash chromatography (hexane/EtOAc/
silica gel gave 5b as a pale-yellow solid (14.0 mg, 0.052 mmol, CH2Cl2 = 2 : 1 : 2) on silica gel gave 6a as a pale-yellow solid
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52% yield), mp 176 °C. H NMR (400 MHz, CDCl3) δ 8.08 (s, (15.40 mg, 0.038 mmol, 38% yield), mp 178–180 °C. H NMR
1H), 7.63 (dd, J = 6.6, 2.9 Hz, 2H), 7.51–7.47 (m, 3H), 7.37 (s, (400 MHz, CDCl3) δ 7.22–7.16 (m, 2H), 7.13 (s, 1H), 6.93 (d, J =
1H), 7.08 (s, 1H), 4.01 (d, J = 5.1 Hz, 6H); 13C NMR (100 MHz, 8.4 Hz, 1H), 6.72 (s, 1H), 6.51 (s, 1H), 3.96 (s, 6H), 3.94 (s, 3H),
CDCl3) δ 181.8, 153.0, 152.6, 149.6, 138.2, 130.5, 129.3, 126.9, 3.89 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 183.3, 163.7, 162.0,
125.8, 125.1, 110.3, 108.8, 56.3, 56.2; HRMS (ESI-QTOF) calcd 151.1, 149.4, 147.8, 141.3, 130.1, 126.6, 120.0, 116.5, 111.3,
for C17H14O3Se 347.0186 ([M + H]+), found 347.0184.
7-Methyl-2-phenyl-4H-selenochromen-4-one (5c). The title calcd for C19H18O5Se 407.0397 ([M + H]+), found 407.0400.
compound was prepared from 1e (22.3 mg, 0.1 mmol). Flash 2-(3,4-Dimethoxyphenyl)-5,6,7-trimethoxy-4H-selenochromen-
chromatography (hexane/EtOAc/CH2Cl2 = 5 : 1 : 2) on silica gel 4-one (6c). The title compound was prepared from 1d (30 mg,
gave 5c as a pale-yellow solid (16.7 mg, 0.075 mmol, 75% 0.1 mmol). Flash chromatography (hexane/EtOAc/CH2Cl2
109.4, 102.9, 99.2, 56.3, 56.1, 56.1, 55.7; HRMS (ESI-QTOF)
=
1
yield), mp 82 °C. H NMR (400 MHz, CDCl3) δ 8.50 (d, J = 8.2 2 : 1 : 2) on silica gel gave 7a as a yellow liquid (17.41 mg,
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Hz, 1H), 7.65–7.61 (m, 2H), 7.51–7.46 (m, 4H), 7.36–7.30 (m, 0.040 mmol, 40% yield). H NMR (400 MHz, CDCl3) δ 7.21 (d,
2H), 2.46 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 182.7, 153.6, J = 11.8 Hz, 2H), 7.13 (s, 1H), 6.94 (d, J = 11.8 Hz, 2H), 3.97 (d,
142.5, 138.2, 137.0, 130.6, 129.9, 129.5, 129.32, 129.28, 128.2, J = 2.0 Hz, 6H), 3.96 (s, 3H), 3.94 (d, J = 1.6 Hz, 6H); 13C NMR
126.9, 125.7, 21.5; HRMS (ESI-QTOF) calcd for C16H12OSe (100 MHz, CDCl3) δ 182.9, 156.6, 156.1, 151.1, 149.5, 148.9,
301.0132 ([M + H]+), found 301.0136.
143.0, 134.0, 130.2, 125.8, 120.9, 119.9, 111.3, 109.4, 105.7,
6-Fluoro-2-phenyl-4H-selenochromen-4-one (5d). The title 62.0, 61.4, 59.2, 56.1, 56.1; HRMS (ESI-QTOF) calcd for
compound was prepared from 1f (22.7 mg, 0.1 mmol). Flash C20H20O6Se 437.0503 ([M + H]+), found 437.0502.
chromatography (hexane/EtOAc/CH2Cl2 = 5 : 1 : 2) on silica gel
gave 5d as a pale-yellow solid (9.5 mg, 0.042 mmol, 42% yield), 4-one (6d). The title compound was prepared from 1d (30 mg,
5,6,7-Trimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-selenochromen-
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mp 155 °C. H NMR (400 MHz, CDCl3) δ 8.32 (dd, J = 9.8, 2.9 0.1 mmol). Flash chromatography (hexane/EtOAc/CH2Cl2
=
Hz, 1H), 7.71 (dd, J = 8.7, 5.0 Hz, 1H), 7.66–7.62 (m, 2H), 2 : 1 : 2) on silica gel gave 7b as a pale-yellow solid (13.96 mg,
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7.53–7.49 (m, 3H), 7.38 (s, 1H), 7.34 (td, J = 8.5, 2.9 Hz, 1H); 0.030 mmol, 30% yield), mp 195–197 °C. H NMR (400 MHz,
13C NMR (100 MHz, CDCl3) δ 181.9 (d, J = 2.3 Hz), 162.4 (d, J = CDCl3) δ 7.19 (s, 1H), 6.93 (s, 1H), 6.83 (s, 2H), 3.97 (d, J = 3.3
248.7 Hz), 154.6, 137.9, 133.6 (d, J = 6.6 Hz), 131.6 (d, J = 2.7 Hz, 6H), 3.93 (s, 9H), 3.91 (s, 3H); 13C NMR (100 MHz, CDCl3)
Hz), 130.9, 130.2 (d, J = 7.3 Hz), 129.4, 126.9, 124.9, 120.2 (d, δ 182.9, 156.7, 156.2, 153.7, 149.1, 143.1, 140.0, 134.0, 133.2,
J = 23.7 Hz), 115.8 (d, J = 22.8 Hz); HRMS (ESI-QTOF) calcd for 126.5, 120.9, 105.7, 104.2, 62.0, 61.4, 61.0, 56.3, 56.2; HRMS
C15H9FOSe 326.9700 ([M + Na]+), found 326.9736.
(ESI-QTOF) calcd for C21H22O7Se 467.0609 ([M + H]+), found
2-Phenyl-6-(trifluoromethyl)-4H-selenochromen-4-one (5e). 467.0605.
The title compound was prepared from 1g (27.7 mg,
0.1 mmol). Flash chromatography (hexane/EtOAc/CH2Cl2
=
5 : 1 : 2) on silica gel gave 5e as a pale-yellow solid (15.2 mg,
Acknowledgements
0.055 mmol, 55% yield), mp 175 °C. 1H NMR (400 MHz,
CDCl3) δ 8.89 (s, 1H), 7.84 (d, J = 8.3 Hz, 1H), 7.76 (d, J = 8.2 We are grateful to Mirae Fine Chemical Co., Ltd and Vismer
Hz, 1H), 7.66–7.62 (m, 2H), 7.54–7.50 (m, 3H), 7.40 (s, 1H); 13
C
Co., Ltd for technical assistance.
NMR (100 MHz, CDCl3) δ 181.7, 154.3, 140.7, 137.6, 131.9,
131.1, 130.3 (q, J = 33.5 Hz), 129.5, 129.3, 127.5 (q, J = 3.4 Hz),
127.4 (q, J = 4.1 Hz), 126.9, 125.6, 123.6 (q, J = 272.6 Hz);
HRMS (ESI-QTOF) calcd for C16H9F3OSe 376.9668 ([M + Na]+),
found 376.9667.
Notes and references
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S. Hendrich and W. Wang, Pharmacol. Ther., 2001, 90, 157;
(c) W. Ren, Z. Qiao, H. Wang, L. Zhu and L. Zhang, Med.
Res. Rev., 2003, 23, 519; (d) H. P. Kim, K. H. Son,
H. W. Chang and S. S. Kang, J. Pharmacol. Sci., 2004, 96,
229; (e) O. Benavente-Garcia and J. Castillo, J. Agric. Food
Chem., 2008, 56, 6185; (f) A. Kumar and R. Pratap, Nat.
Prod. Rep., 2010, 27, 1571; (g) M. Singh, M. Kaur and
O. Silakari, Eur. J. Med. Chem., 2014, 84, 206.
2 C. M. Weekley and H. H. Harris, Chem. Soc. Rev., 2013, 42,
8870.
3 (a) Y.-S. Choi, Y.-J. Kim, J.-Y. Lee, J. Lee and J.-H. Jeong,
Heterocycles, 2014, 89, 2794; (b) Y.-S. Choi, Y.-J. Kim,
S. Yang, J.-H. Jeong, D.-M. Kim, K.-T. Lee and J. H. Ryu,
Int. J. Mol. Sci., 2015, 16, 29574.
2-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-4H-selenochromen-
4-one (6a). The title compound was prepared from 1b
(26.9 mg, 0.1 mmol). Flash chromatography (hexane/EtOAc/
CH2Cl2 = 2 : 1 : 2) on silica gel gave 5a as a pale-yellow solid
1
(24.32 mg, 0.060 mmol, 60% yield), mp 205–206 °C. H NMR
(400 MHz, CDCl3) δ 8.06 (s, 1H), 7.33 (s, 1H), 7.22 (d, J = 8.3
Hz, 1H), 7.15 (s, 1H), 7.06 (s, 1H), 6.95 (d, J = 8.4 Hz, 1H), 4.00
(d, J = 6.8 Hz, 6H), 3.95 (d, J = 6.3 Hz, 6H); 13C NMR (100 MHz,
CDCl3) δ 182.0, 152.9, 152.6, 151.2, 149.6, 149.5, 130.9, 130.4,
125.9, 124.0, 119.9, 111.4, 110.3, 109.5, 108.8, 56.3, 56.2, 56.1;
HRMS (ESI-QTOF) calcd for C19H18O5Se 407.0397 ([M + H]+),
found 407.0391.
2-(3,4-Dimethoxyphenyl)-5,7-dimethoxy-4H-selenochromen-
4-one (6b). The title compound was prepared from 1c
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