Molecules 2018, 23, 600
7 of 14
1-Isopropyl-3-(7-methoxy-2-oxo-4-(trifluoromethyl)-2H-chromen-6-yl) urea (5c). Light yellow solid; yield: 54.2%;
m.p. 224 ◦C; 1H-NMR (500 MHz, DMSO)
: 8.66 (s, 1H), 8.07 (s, 1H), 7.20 (s, 1H), 6.90 (d, J = 7.2 Hz, 1H)
6.80 (s, 1H), 3.99 (s, 3H), 3.82–3.72 (m, 1H), 1.10 (d, J = 6.4 Hz, 6H); 13C-NMR (126 MHz, DMSO)
δ
,
δ:
159.45, 154.74, 152.11, 150.28, 140.42 (q, J = 31.5 Hz), 128.03, 122.16 (q, J = 275.94 Hz), 113.43 (q, J = 5.0 Hz),
111.36 (q, J = 2.52 Hz), 106.06, 100.11, 57.22, 41.36, 23.41; ESI-MS m/z: 345.30 [M + Na]+ (calculated for
C15H16F3N2O4, 345.21).
1-(tert-Butyl)-3-(7-methoxy-2-oxo-4-(trifluoromethyl)-2H-chromen-6-yl) urea (5d). yellow solid; Yield: 31.1%;
m.p. 237 ◦C; 1H-NMR (500 MHz, CDCl3)
δ
: 8.54 (s, 1H), 6.87 (s, 1H), 6.83 (s, 1H), 6.64 (s, 1H), 4.90 (s, 1H),
3.93 (s, 3H), 1.40 (s, 9H); 13C-NMR (126 MHz, CDCl3)
δ: 159.76 (q, J = 6.2 Hz), 152.2 (q, J = 22.68 Hz), 151.92
(q, J = 5.5 Hz), 150.76 (q, J = 7.3 Hz), 142.11 (q, J = 32.76 Hz), 127.15 (q, J = 12.2 Hz), 121.57 (q, J = 275.94 Hz),
113.46 (q, J = 2.52 Hz), 112.58 (q, J =5.04 Hz), 106.85, 98.98 (q, J = 6.2 Hz), 56.33, 51.03, 29.31; HR-ESI-MS
m/z: 381.1038 [M + Na]+ (calculated for C16H17F3N2NaO4, 381.1038).
1-Hexyl-3-(7-methoxy-2-oxo-4-(trifluoromethyl)-2H-chromen-6-yl) urea (5e). Light yellow solid; yield: 31.2%;
◦
1
m.p. 143 C; H-NMR (500 MHz, CDCl3)
(t, J = 5.0 Hz, 1H), 3.89 (s, 3H), 3.28 (q, J = 5 Hz, 2H), 1.58–1.48 (m, 2H), 1.38–1.20 (m, 6H), 0.85 (t, J = 6.6 Hz,
3H); 13C-NMR (126 MHz, CDCl3)
: 159.73, 154.77, 151.80, 150.85, 142.13 (q, J = 32.76 Hz), 126.90, 122.63
δ: 8.68 (s, 1H), 7.29 (s, 1H), 6.82 (s, 1H), 6.63 (s, 1H), 5.47
δ
(q, J = 122.37 Hz), 113.61 (q, J = 1.26 Hz), 112.66 (q, J = 5.04 Hz), 106.90, 98.98, 56.38, 40.53, 31.50, 29.99, 26.56,
22.57, 14.00; HR-ESI-MS m/z: 409.1346 [M + Na]+ (calculated for C18H21F3N2NaO4, 409.1351).
1-Cyclopentyl-3-(7-methoxy-2-oxo-4-(trifluoromethyl)-2H-chromen-6-yl) urea (5f). Light yellow solid; yield:
◦
1
43.6%; m.p. 225 C; H-NMR (500 MHz, DMSO)
(d, J = 6.9 Hz, 1H), 6.81 (s, 1H), 4.00 (s, 3H), 3.97-3.91 (m, 1H), 1.90–1.81 (m, 2H), 1.72–1.48 (m, 4H),
1.45–1.31 (m, 2H); 13C-NMR (126 MHz, DMSO)
: 159.49, 155.02, 152.10, 150.30, 140.42 (q, J = 32.76 Hz),
δ: 8.68 (s, 1H), 8.07 (s, 1H), 7.21 (s, 1H), 7.01
δ
128.04, 122.29(q, J = 273.42 Hz),113.52 (q, J = 1.26 Hz), 111.34 (q, J = 2.52 Hz), 106.10, 100.18, 57.27, 51.28,
33.30, 23.59; HR-ESI-MS m/z: 393.1033 [M + Na]+ (calculated for C17H17F3N2NaO4, 393.1038).
1-Cyclohexyl-3-(7-methoxy-2-oxo-4-(trifluoromethyl)-2H-chromen-6-yl) urea (5g). Light yellow solid; yield
◦
1
48.9%; m.p. 265 C; H-NMR (500 MHz, DMSO)
(d, J = 7.5 Hz, 1H), 6.82 (s, 1H), 3.99 (s, 3H), 3.54–3.45 (m, 1H),1.86–1.76 (m, 2H), 1.72–1.63 (m, 2H),
1.37–1.11 (m, 6H); 13C-NMR (126 MHz, DMSO)
: 159.48, 154.70, 152.14, 150.29, 140.42 (q, J = 31.5 Hz),
δ: 8.68 (s, 1H), 8.13 (s, 1H), 7.23 (s, 1H), 6.95
δ
128.06, 122.28(q, J = 275.94 Hz), 113.49(q, J = 6.3 Hz), 111.40 (q, J = 2.52 Hz), 106.09, 100.18, 57.27, 48.02,
33.35, 25.70, 24.71; HR-ESI-MS m/z: 407.1191 [M + Na]+ (calculated for C18H19F3N2NaO4, 407.1195).
1-(2-(3-(Prop-1-en-2-yl)phenyl)propan-2-yl)-3-(7-methoxy-2-oxo-4-(trifluoromethyl)-2H-chromen-6-yl) urea
◦
(
5h). Light yellow solid; yield: 20.0%; m.p. 228–229 C; 1H-NMR (500 MHz, DMSO)
δ
: 8.52 (s, 1H), 8.29
(s, 1H), 7.50 (s, 1H), 7.47 (s, 1H), 7.39–7.29 (m, 3H), 7.22 (s, 1H), 6.79 (s, 1H), 5.38 (s, 1H), 5.08 (s, 1H)
4.01 (s, 3H), 2.11 (s, 3H), 1.62 (s, 6H); 13C-NMR (126 MHz, DMSO)
: 159.43, 154.39, 152.20, 150.33,
,
δ
148.72, 143.45, 140.62, 140.34 (q, J = 31.5 Hz), 128.54, 128.04, 124.66, 123.56, 122.22 (q, J = 275.94 Hz),
122.21, 113.47 (q, J = 6.3 Hz), 112.89, 111.22, 106.03, 100.21, 57.29, 55.01, 30.25, 22.01; HR-ESI-MS m/z:
483.1504 [M + Na]+ (calculated for C24H23F3N2NaO4, 483.1508).
1-Phenethyl-3-(7-methoxy-2-oxo-4-(trifluoromethyl)-2H-chromen-6-yl) urea (5i). Light yellow solid; yield:
◦
1
41.7%; m.p. 222 C; H-NMR (500 MHz, DMSO)
7.27–7.24 (m, 2H), 7.23–7.18 (m, 2H), 6.99 (t, J = 5.1 Hz, 1H), 6.82 (s, 1H), 3.98 (s, 3H), 3.38
(q, J = 6.6 Hz, 2H), 2.75 (t, J = 7.0 Hz, 2H) : 159.46, 155.48, 152.21, 150.38,
13C-NMR (126 MHz, DMSO)
δ: 8.68 (s, 1H), 8.22 (s, 1H), 7.36–7.29 (m, 2H),
;
δ
140.40 (q, J = 31.5 Hz), 139.96, 129.17, 128.84, 127.96, 126.57, 122.28 (q, J = 275.94 Hz), 113.53 (q, J = 6.3Hz)
,
111.57 (q, J = 1.26 Hz), 106.09, 100.21, 57.25, 40.92, 36.20; HR-ESI-MS m/z: 429.1038 [M + Na]+ (calculated
for C20H17F3N2NaO4, 429.1038).
1-(2-Chlorophenyl)-◦3-(7-methoxy-2-oxo-4-(trifluoromethyl)-2H-chromen-6-yl) urea (5j). Yellow solid; yield:
1
45.0%; m.p. 231 C; H-NMR (500 MHz, DMSO)
δ
: 9.76 (s, 1H), 8.64 (s, 1H), 8.52 (s, 1H), 7.96
(s, 1H), 7.68–7.44 (m, 2H), 7.33 (d, J = 6.2 Hz, 1H), 7.27 (s, 1H), 6.83 (s, 1H), 4.03 (s, 3H); 13C-NMR