1508
D. W. Zhang et al./Chemical Papers 69 (11) 1500–1511 (2015)
Table 5. (continued)
Compound
Spectral data
VIId
VIIe
VIIf
IR (KBr), ν˜/cm−1: 3130, 3073, 2920, 1730, 1620, 1577, 1540, 1500, 1447, 1408, 1350, 1110, 1051, 926, 866, 756, 694,
674, 555
1H NMR (300 MHz, CDCl3), δ: 8.64 (t, J = 1.8 Hz, 1H, 3-nitrophenyl H2), 8.43 (d, J = 1.4 Hz, 1H, 3-nitrophenyl
H4), 8.37–8.27 (m, 1H, 3-nitrophenyl H6), 8.23–8.14 (m, 1H, 3-nitrophenyl H5), 7.77–7.61 (m, 2H, 2-chlorophenyl
H3, H6), 7.54–7.45 (m, 1H, 2-chlorophenyl H5), 7.38 (dd, J = 11.7 Hz, 3.8 Hz, 1H, 2-chlorophenyl H4), 6.82 (s, 1H,
isoxazolyl H4), 6.74 (s, 1H, isoxazolyl H4), 4.83 (d, J = 0.9 Hz, 4H, CH2)
13C NMR ((CD3)2SO, 125 MHz), δ: 169.8, 167.7, 161.2, 160.7 (isoxazolyl C1, C3), 148.6, 132.9, 132.5 (3-
nitrophenyl C1, C3, C6), 131.1, 131.0 (2-chlorophenyl C2, C3), 130.6 (3-nitrophenyl C2), 130.5, 130.1, 127.9, 127.2
(2-chlorophenyl C1, C4, C5, C6), 124.7, 121.8 (3-nitrophenyl C4, C5), 105.1, 101.5 (isoxazolyl C2), 63.6, 63.5 (CH2)
HRMS, m/z: 412.0686 (calc. 412.0701) [M + H]+
IR (KBr), ν˜/cm−1: 3130, 3092, 2920, 1730, 1620, 1577, 1540, 1500, 1460, 1430, 1350, 1090, 999, 906, 869, 810, 739,
694, 501
1H NMR (300 MHz, CDCl3), δ: 8.61 (s, 1H, 3-nitrophenyl H2), 8.30 (s, 1H, 3-nitrophenyl H4), 8.15 (s, 1H, 3-
nitrophenyl H6), 7.75 (d, J = 2.1 Hz, 1H, 3-nitrophenyl H5), 7.72 (s, 1H, 4-chlorophenyl H2), 7.66 (s, 1H, 4-
chlorophenyl H6), 7.44 (s, 2H, 4-chlorophenyl H3, H5), 6.73 (s, 1H, isoxazolyl H4), 6.62 (s, 1H, isoxazolyl H4), 4.82
(d, J = 4.4 Hz, 4H, CH2)
13C NMR ((CD3)2SO, 125 MHz), δ: 169.8, 168.9, 161.6, 160.7 (isoxazolyl C1, C3), 148.6, 136.3, 132.5, 130.5 (3-
nitrophenyl C1, C2, C3, C6), 130.1, 129.3, 128.1, 127.1 (4-chlorophenyl C), 124.8, 121.8 (3-nitrophenyl C4, C5),
101.7, 101.6 (isoxazolyl C2), 63.6, 63.5 (CH2)
HRMS, m/z: 411.9960 (calc. 412.0701) [M + H]+
IR (KBr), ν˜/cm−1: 3132, 2866, 1869, 1734, 1531, 1352, 1229, 1090, 1003, 822, 696
1H NMR (300 MHz, CDCl3), δ: 8.64–8.60 (m, 1H, 3-nitrophenyl H2), 8.32 (ddd, J = 8.2 Hz, 2.1 Hz, 0.9 Hz, 1H,
3-nitrophenyl H4), 8.20–8.15 (m, 1H, 3-nitrophenyl H6), 7.82–7.76 (m, 2H, 4-fluorophenyl H2, H6), 7.67 (t, J =
8.0 Hz, 1H, 3-nitrophenyl H5), 7.19–7.11 (m, 2H, 4-fluorophenyl H3, H5), 6.73 (s, 1H, isoxazolyl H4), 6.61 (s, 1H,
isoxazolyl H4), 4.81 (d, J = 8.6 Hz, 4H, CH2)
13C NMR ((CD3)2SO, 125 MHz), δ: 169.8, 168.7 (isoxazolyl C1), 164.9 (4-fluorophenyl C4), 162.9, 161.6 (isoxazolyl
C3), 160.7, 132.5, 130.5, 130.1 (3-nitrophenyl C1, C2, C3, C6), 128.8, 128.7, 124.9, 124.8 (4-fluorophenyl C1, C2,
C4, C6), 121.8, 116.2 (3-nitrophenyl C4, C5), 116.0 (4-fluorophenyl C3, C5), 101.6, 101.5 (isoxazolyl C2), 63.6, 63.5
(CH2)
HRMS, m/z: 396.0991 (calc. 396.0996) [M + H]+
VIIg
IR (KBr), ν˜/cm−1: 3111, 2926, 1699, 1533, 1348, 1097, 910, 694
1H NMR (300 MHz, CDCl3), δ: 8.62 (s, 2H, 3-nitrophenyl H2), 8.32 (d, J = 7.3 Hz, 2H, 3-nitrophenyl H4), 8.18 (d,
J = 7.7 Hz, 2H, 3-nitrophenyl H6), 7.67 (t, J = 8.0 Hz, 2H, 3-nitrophenyl H5), 6.74 (s, 2H, isoxazolyl H4), 4.84 (s,
4H, CH2)
13C NMR ((CD3)2SO, 125 MHz), δ: 169.9, 160.7 (isoxazolyl C1, C3), 148.7, 132.5, 130.5, 130.2, 124.8, 121.8 (3-
nitrophenyl C), 101.6 (isoxazolyl C2), 63.6 (CH2)
HRMS, m/z: 423.0945 (calc. 423.0941) [M + H]+
VIIIa
IR (KBr), ν˜/cm−1: 3120, 3092, 2960, 2040, 1720, 1600, 1520, 1440, 1350, 1260, 1090, 953, 852, 768, 698, 579, 486
1H NMR (300 MHz, CDCl3), δ: 8.36–8.26 (m, 2H, 4-nitrophenyl H3, H5), 7.97 (d, J = 9.0 Hz, 2H, 4-nitrophenyl H2,
H6), 7.86 (dd, J = 7.7 Hz, 1.7 Hz, 1H, 2-methoxyphenyl H6), 7.48–7.36 (m, 1H, 2-methoxyphenyl H4), 7.09–6.95
(m, 2H, 2-methoxyphenyl H3, H5), 6.84 (s, 1H, isoxazolyl H4), 6.70 (s, 1H, isoxazolyl H4), 4.80 (d, J = 4.2 Hz, 4H,
CH2), 3.89 (s, 3H, OCH3)
13C NMR ((CD3)2SO, 125 MHz), δ: 170.1, 167.0, 160.7, 160.2 (isoxazolyl C1, C3), 157.2 (2-methoxyphenyl C2),
148.8, 134.9 (4-nitrophenyl C1, C4), 131.5, 130.9 (2-methoxyphenyl C4, C6), 129.4, 128.9, 127.7, 124.2 (4-nitrophenyl
C2, C3, C5 C6), 121.0, 117.5, 111.5 (2-methoxyphenyl C1, C3, C5), 105.5, 101.6 (isoxazolyl C2), 63.5, 63.3 (CH2),
55.6 (OCH3)
HRMS, m/z: 408.1192 (calc. 408.1197) [M + H]+
VIIIb
IR (KBr), ν˜/cm−1: 3130, 3092, 2940, 1720, 1600, 1520, 1469, 1430, 1340, 1260, 1180, 1090, 1030, 914, 856, 698, 482
1H NMR (300 MHz, CDCl3), δ: 8.32 (d, J = 8.9 Hz, 2H, 4-nitrophenyl H3, H5), 7.97 (d, J = 8.9 Hz, 2H, 4-nitrophenyl
H2, H6), 7.73 (d, J = 8.9 Hz, 2H, 4-methoxyphenyl H2, H6), 6.97 (d, J = 8.8 Hz, 2H, 4-methoxyphenyl H3, H5),
6.70 (s, 1H, isoxazolyl H4), 6.58 (s, 1H, isoxazolyl H4), 4.79 (d, J = 8.0 Hz, 4H, CH2), 3.86 (s, 3H, OCH3)
13C NMR ((CD3)2SO, 125 MHz), δ: 170.6, 169.2 (isoxazolyl C1), 162.0 (4-methoxyphenyl C4), 161.2, 161.0 (isoxa-
zolyl C3), 148.9, 134.9 (4-nitrophenyl C1, C4), 128.6 (4-methoxyphenyl C2, C6), 128.4, 124.8 (4-nitrophenyl C2, C3,
C5, C6), 121.2, 115.0 (4-methoxyphenyl C1, 3C, 5C), 103.1, 102.4 (isoxazolyl C4), 63.2, 63.1 (CH2), 55.8 (OCH3)
HRMS, m/z: 408.1173 (calc. 408.1197) [M + H]+
VIIIc
IR (KBr), ν˜/cm−1: 3130, 3087, 2920, 1730, 1620, 1520, 1430, 1340, 1100, 1000, 852, 810, 698, 513
1H NMR (300 MHz, CDCl3), δ: 8.36–8.26 (m, 2H, 4-nitrophenyl H3, H5), 8.02–7.92 (m, 2H, 4-nitrophenyl H2, H6),
7.72–7.54 (m, 2H, 4-methylphenyl H2, H6 ), 7.26 (d, J = 7.9 Hz, 2H, 4-methylphenyl H3, H5), 6.70 (s, 1H, isoxazolyl
H4), 6.60 (s, 1H, isoxazolyl H4), 4.80 (d, J = 6.6 Hz, 4H, CH2), 2.40 (s, 3H, CH3)
13C NMR ((CD3)2SO, 125 MHz), δ: 169.4, 162.3, 161.0 (isoxazolyl C1, C3), 148.9, 140.5 (4-nitrophenyl C1, C4),
134.9, 132.6, 130.1 (4-methylphenyl C3, C4, C5), 129.1, 128.4 (4-nitrophenyl C2, C6), 127.0, 126.1 (4-methylphenyl
C1, C2, C6), 124.8 (4-nitrophenyl C3 C5), 103.1, 102.6 (isoxazolyl C2), 63.2, 63.1 (CH2), 21.4 (CH3)
HRMS, m/z: 392.1233 (calc. 392.1248) [M + H]+
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