Y. M. Xia et al./Chemical Papers 68 (3) 384–391 (2014)
Table 3. Spectral data of newly prepared compounds
389
Compound
Spectral data
−
III
IR, ν˜ /cm 1: 2950, 2848, 1764, 1643, 1580, 1508, 1220
1
H NMR (500 MHz, DMSO-d6), δ: 3.84 (s, 3H, OCH3), 4.82 (s, 2H, CH2), 7.05–7.07 (d, 1H, J = 8 Hz, ArH), 7.42
s, 1H, ArH), 7.50–7.52 (d, 1H, J = 8.0 Hz, ArH), 9.84 (s, 1H, CH—O), 11.46 (s, 1H, COOH)
C NMR (DMSO-d6, 125 MHz), δ: 56.0 (OCH3), 65.2 (CH2), 110.5, 112.7, 126.1, 130.5, 149.6, 152.9, 170.1 (COOH),
91.9 (CH—O)
HRMS, m/z (found/calc.): 210.0542/210.0528 (M+, C10H10O5)
(
1
3
1
−
IV
V
IR, ν˜ /cm 1: 2856, 1739, 1677, 1590, 1508, 1226
1
H NMR (500 MHz, CDCl3), δ: 3.84 (s, 3H, OCH3), 3.98 (s, 3H, OCH3), 4.82 (s, 2H, CH2), 6.89–6.90 (d, 1H, J =
.0 Hz, ArH), 7.23 (s, 1H, ArH), 7.46–7.47 (d, 1H, J = 8.0 Hz, ArH), 9.89 (s, 1H, CH—O)
C NMR (125 MHz, CDCl3), δ: 52.5 (OCH3), 56.2 (OCH3), 65.9 (CH2), 109.8, 112.3, 126.2, 131.2, 149.9, 152.5,
68.6 (C—O), 190.9 (CH—O)
HRMS, m/z (found/calc.): 224.0663/224.0685 (M+, C11H12O5)
8
13
1
IR, ν˜ /cm 1: 1743, 1598, 1512, 1216
−
1
H NMR (500 MHz, CDCl3), δ: 3.32 (s, 6H, C(OCH3)2), 3.79 (s, 3H, OCH3), 3.90 (s, 3H, OCH3), 4.70 (s, 2H,
CH2COO), 5.32 (s, 1H, CH), 6.81 (s, 1H, ArH), 6.94 (d, 1H, J = 8.0 Hz, ArH), 7.02 (d, 1H, J = 8.0 Hz, ArH)
13
C NMR(125 MHz, CDCl3), δ: 52.3 (OCH3), 52.8 (OCH3), 55.9 (OCH3), 66.3 (OCH3), 75.7 (CH2), 103.4 (CH),
10.4, 112.7, 119.8, 132.7, 147.6, 149.8, 171,6 (C—O)
HRMS, m/z (found/calc.): 270.1125/270.1103 (M+, C13H18O6)
1
IR, ν˜ /cm 1: 2832, 1684, 1591, 1509, 1266
−
VI
1
H NMR (500 MHz, CDCl3), δ: 3.30 (s, 3H, OCH3), 3.84 (s, 3H, ArOCH3), 6.02 (s, 2H, OCH2), 7.18–7.40 (m, 3H,
ArH), 9.83(s, 1H, CH—O)
1
3C NMR (125 MHz, CDCl3), δ: 55.6 (OCH3), 56.1 (ArOCH3), 95.2 (OCH2), 108.4, 109.5, 124.6, 130.5, 150.3,
1
55.7, 191.5 (CH—O)
HRMS, m/z (found/calc.): 196.2129/196.2103 (M+, C10H12O4)
−
VII
VIII
IR, ν˜ /cm 1: 2849, 1716, 1680, 1593, 1504, 1267
1
H NMR (500 MHz, CDCl3), δ: 3.47 (s, 3H, OCH3), 3.74 (s, 3H, OCH3), 3.77 (s, 3H, OCH3), 4.02 (s, 3H, OCH3),
.22 (s, 2H, CH2OCH3), 6.88–7.52 (m, 6H, ArH), 7.23 (s, 1H, CH), 9.85 (s, 1H, CH—O)
5
13
C NMR (125 MHz, CDCl3), δ: 52.9 (CH3), 55.6 (CH3), 56.4 (2 × CH3), 94.9 (CH2), 111.6, 113.7, 116.4, 124.7,
1
25.7, 126.1, 128.2, 129.4, 131.9, 132.3, 137.4, 148.1, 149.4, 150.7, 161.4 (CO), 191.9 (CH—O)
+
HRMS, m/z (found/calc.): 386.1352/386.1366 (M , C21H22O7)
IR, ν˜ /cm 1: 3024, 2956, 1715, 1596, 1510, 1260
−
1
H NMR (500 MHz, CDCl3), δ: 1.32 (t, 3H, J = 7.0 Hz, CH2CH3), 3.49 (s, 3H, OCH3), 3.73 (s, 3H, OCH3), 3.74
(s, 3H, OCH3), 3.94 (s, 3H, OCH3), 4.24 (q, 2H, J = 7.0 Hz, CH2CH3), 5.21 (s, 2H, OCH2OCH3), 6.32 (d, 1H, J
=
15.0 Hz, ArCHCH), 6.73–7.40 (m, 6H, ArH), 7.24 (s, 1H, CH), 7.57 (d, 1H, J = 15.0 Hz, ArCHCH)
C NMR (125 Hz, CDCl3), δ: 14.4, 52.6 (OCH3), 55.5 (OCH3), 55.9 (OCH3), 56.2 (OCH3), 60.5 (CH2), 95.0
1
3
(
1
CH2), 111.0, 111.3, 113.8, 115.3, 116.9, 122.1, 124.8, 126.4, 128.1, 129.5, 137.9, 144.2, 147.5, 148.0, 149.1, 149.4,
63.9 (C—O), 167.1 (C—O)
HRMS, m/z (found/calc.): 456.1792/456.1784 (M+, C25H28O8)
IR, ν˜ /cm 1: 3027, 2944, 1690, 1594, 1511, 1256
−
IX
1
H NMR (500 MHz, DMSO-d6), δ: 3.51 (s, 3H, OCH3), 3.92 (s, 3H, OCH3), 3.94 (s, 3H, OCH3), 5.31 (s, 2H,
OCH2OCH3), 6.43 (d, 1H, J = 15.0 Hz, ArCHCHCOO), 7.23 (s, 1H, CH), 6.73–7.4 (m, 6H, ArH), 7.50 (d, 1H, J =
1
5.0 Hz, ArCH—CHCOO), 11.62 (s, 2H, 2 × COOH)
13
C NMR (125 Hz, DMSO-d6), δ: 55.8 (OCH3), 56.4 (OCH3), 56.5 (OCH3), 95.0 (CH2), 112.2, 113.7, 113.9, 116.6,
18.2, 122.7, 124.4, 126.9, 127.1, 129.5, 138.9, 144.4, 147.7, 147.8, 149.2, 149.9, 161.6 (CO), 168.4 (C—O)
1
+
HRMS, m/z (found/calc.): 414.1330/414.1315 (M , C22H22O8)
IR, ν˜ /cm 1: 3322, 3300, 3015, 2915, 2889, 2806, 1670, 1594, 1513
−
XI
1
H NMR (500 MHz, CDCl3), δ: 2.79 (t, 2H, J = 7.0 Hz, ArCH2), 3.55 (t, 2H, J = 7.0 Hz, CH2N), 5.21 (s, 1H,
ArOH), 6.32 (s,1H, NH), 6.79 (d, 2H, J = 8.5 Hz, ArH), 7.09 (d, 2H, J = 8.5 Hz, ArH), 8.15 (s, 1H, CH—O)
1
3
C NMR (125 Hz, CDCl3), δ: 35.2 (CH2), 39.2 (CH2), 161.4, 130.3, 115.7, 130.3, 115.9, 132.6, 203.9 (CH—O)
HRMS, m/z (found/calc.): 165.0772/165.0790 (M+, C9H11NO2)
IR, ν˜ /cm 1: 3324, 3012, 2917, 2880, 2811, 1674, 1591, 1510, 1365, 1253
−
XII
1
H NMR (500 MHz, CDCl3), δ: 1.50–1.90 (m, 6H, CH2CH2CH2), 2.79 (t, 2H, J = 7.0 Hz, ArCH2), 3.55 (m, 2H,
CH2), 3.91 (t, 2H, J = 7.0 Hz, CH2N), 5.39 (s,1H, OCH), 6.30 (s,1H, NH), 6.99 (d, 2H, J = 8.0 Hz, ArH), 7.12 (d,
2
H, J = 8.0 HZ, ArH), 8.11 (s, 1H, CH—O)
1
3
C NMR (125 Hz, CDCl3), δ: 19.0, 25.4, 30.5, 34.8, 39.5, 62.3, 96.6, 116.9 (2 × Ar), 129.8 (2 × Ar), 131.6, 161.3,
07.2 (CH—O)
HRMS, m/z (found/calc.): 249.1384/249.1365 (M+, C14H19NO3)
2
IR, ν˜ /cm 1: 3332, 3282, 3036, 2932, 1591, 1253, 1510
−
XIII
1
H NMR (500 MHz, CDCl3), δ: 1.59–1.87 (m, 6H, CH2CH2CH2), 2.57 (t, 2H, J = 7.0 Hz, ArCH2), 2.72 (t, 2H,
J = 7.0 Hz, CH2N), 3.50–3.78 (m, 2H, CH2), 5.40 (s, 1H, OCH), 6.92 (d, 2H, J = 7.5 Hz, ArH), 7.10 (d, 2H, J =
7
.5 Hz, ArH)
1
3
C NMR (125 Hz, CDCl3), δ: 19.2, 25.2, 30.4, 35.5, 44.1, 62.0, 96.4, 116.8 (2 × Ar), 129.9 (2 × Ar), 133.7, 155.4
HRMS, m/z (found/calc.): 221.1435/221.1416 (M+, C13H19NO2)