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13 Analytical and Spectroscopic Data
of Selected Compounds:
Compound 9:
white solid; mp 147-149 ˚C. ¹H
NMR (300 MHz, DMSO-d
6): δ = 9.20
(br s, 1 H), 6.94 (d, J = 8.4
Hz, 2 H), 6.71 (d, J = 7.9 Hz,
1 H), 6.63 (d, J = 8.4 Hz, 2
H), 6.52 (d, J = 7.9 Hz, 1 H),
5.94 (s, 2 H), 3.82 (s, 3 H), 3.56 (s, 2 H), 3.41 (br s, 1 H), 2.54-2.63
(m, 4 H). ¹³C NMR (75 MHz, DMSO-d
6): δ = 155.44,
147.90, 141.40, 136.26, 130.49, 129.45, 125.94, 122.06, 115.07,
102.30, 100.89, 59.47, 50.51, 47.68, 35.00. HRMS: m/z [M+] calcd
for C17H19NO4: 301.1314; found:
301.1302.
Compound 10: colorless
oil. ¹H NMR (300 MHz, CDCl3):
δ = 6.98-7.02
(m, 2 H), 6.74-6.80 (m, 2 H), 6.51-6.53 (m, 2
H), 5.94 (d, J = 3.0 Hz, 2 H),
5.20 (br s, 1 H), 4.63 (s, 1 H), 4.42 (s, 1 H), 4.01 (d, J = 7.8 Hz, 3 H), 3.41-3.50
(m, 2 H),
2.70-2.84 (m, 2 H). ¹³C
NMR (75 MHz, CDCl3): δ = 155.04, 154.84,
150.02, 149.85, 142.43, 142.12, 136.59, 136.53, 130.63, 130.35,
130.24, 129.91, 123.83, 122.10, 120.70, 119.93, 116.01, 115.83,
103.24, 102.95, 101.62, 101.52, 60.04, 59.90, 48.63, 44.59, 34.75,
32.38. HRMS: m/z [M+] calcd
for C19H18F3NO5: 397.1137;
found: 397.1125.
Compound 11:
yellow crystals; mp 142-144 ˚C. ¹H
NMR (300 MHz, CDCl3): δ = 6.94 (m,
1 H), 6.81 (m, 1 H),
6.21-6.27 (m, 3 H), 5.90
(s, 2 H), 4.91 (d, J = 5.7 Hz,
2 H), 4.03 (d, J = 8.0 Hz, 3
H), 3.88 (m, 2 H), 2.36 (t, J = 6.3
Hz, 2 H). ¹³C NMR (75 MHz, CDCl3): δ = 185.65,
185.43, 157.95 (m), 153.18, 152.95, 149.36, 149.32, 141.94, 141.05, 137.25,
136.06, 130.97, 130.46, 127.49, 127.48, 122.57, 122.16, 118.74,
118.55, 114.92, 114.74, 104.94, 104.39, 102.08, 101.73, 60.21, 49.16,
48.71, 45.65 (d, J = 3.4 Hz), 44.64,
40.47 (d, J = 3.4 Hz), 40.00,
35.47, 33.90. HRMS:
m/z [M+] calcd
for C19H16F3NO5: 395.0981;
found: 395.0968.
Compound 12: white crystals; mp 175-177 ˚C
(lit.¹6 mp 177-178 ˚C). ¹H
NMR (300 MHz, DMSO-d
6): δ = 7.86
(d, J = 10.3 Hz, 1 H), 6.93
(s, 1 H), 5.90-5.94 (m, 3 H), 4.03 (d, J = 17.3
Hz, 1 H), 3.88 (s, 3 H), 3.64 (d, J = 17.3
Hz, 1 H), 3.46 (m, 1 H), 3.36 (m, 1 H), 2.81 (m, 1 H), 2.48 (m,
1 H), 2.30 (m, 1 H), 2.13 (m, 2 H). ¹³C
NMR (75 MHz, DMSO-d
6): δ = 197.93,
150.97, 147.91, 140.49, 137.45, 133.57, 127.89, 117.62, 100.71,
97.34, 67.96, 59.00, 57.41, 53.69, 44.48, 44.48, 39.78. HRMS: m/z [M+] calcd
for C17H17NO4: 299.1158; found:
299.1151.
Compound 13: white crystals;
mp 102-104 ˚C. ¹H NMR (600
MHz, DMSO-d
6): δ = 6.67
(s, 1 H), 6.38 (dd, J = 10.2, 2.1
Hz, 1 H), 5.88 (ABq, 2 H), 5.61 (d, J = 10.2
Hz, 1 H), 4.90 (br s, 1 H), 4.16 (m, 1 H), 4.06 (d, J = 17.3 Hz, 1 H), 3.86 (s,
3 H), 3.62 (d, J = 17.3 Hz,
1 H), 3.22 (m, 1 H), 3.02 (dd, J = 13.2,
3.4 Hz, 1 H), 2.77 (m, 1 H), 1.98 (m, 1 H), 1.92 (m, 1 H), 1.82
(m, 1 H), 1.42 (m, 1 H). ¹³C NMR (75
MHz, DMSO-d
6): δ = 147.53,
140.30, 139.77, 133.12, 132.69, 127.65, 117.03, 100.42, 97.14, 65.88,
65.82, 58.86, 57.74, 52.70, 44.73, 43.91, 34.37. HRMS: m/z [M+] calcd
for C17H19NO4: 301.1314; found:
301.1316. The NOESY experiment was recorded on a Bruker Avance DPX-600 MHz
spectrometer at 300.3 K with F2 acquisition parameters D1 = 2.00
s and D8 = 0.89 s using DMSO-d
6 as solvent.
Compound 2: white crystals; mp 165-167 ˚C
(dec.). ¹H NMR (300 MHz, CDCl3): δ = 6.56
(s, 1 H), 6.52 (d, J = 10.0 Hz,
1 H), 5.95 (dd, J = 10.0, 5.1
Hz, 1 H), 5.85 (ABq, 2 H), 4.35 (m, 1 H), 4.28 (d, J = 17.3
Hz, 1 H), 3.97 (s, 3 H), 3.85 (d, J = 17.3
Hz, 1 H), 3.43 (m, 2 H), 2.90 (m, 1 H), 2.15 (m, 2 H), 1.94 (m,
1 H), 1.76 (m, 1 H). ¹³C NMR (75 MHz, CDCl3): δ = 148.23,
140.93, 138.83, 133.45, 131.68, 127.64, 116.42, 100.62, 96.79, 63.72,
62.62, 59.14, 58.40, 53.56, 44.22, 43.68, 32.39. HRMS: m/z [M+] calcd
for C17H19NO4: 301.1314; found:
301.1307.
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