RSC Advances
Paper
ꢂ1
6
4
68 cm ; HRMS (ESI) anal. calcd for C20
H
13
F
3
N
2
NaO
4
m/z Hz), 105.3, 45.9, 22.5 ppm; IR (KBr): 3412, 1745, 1587, 1511, 1284,
+
ꢂ1
25.0719 [M + Na] , found 425.0717.
1134, 826 cm ; HRMS (ESI) anal. calcd for C H BrF NNaO m/z
19
13
3
4
+
3
.1.3 N-((7-Hydroxy-2-oxo-4-(triuoromethyl)-2H-chromen- 477.9872 [M + Na] , found 477.9875.
ꢀ
1
8
(
yl)phenyl)methyl)acetamide) (6b). Mp 251–253 C; H NMR
+ DMSO-d
): d 7.80 (d, J ¼ 9.4 Hz, 1H), 7.49 (d, methyl)-2H-chromen-8-yl)methyl)acetamide (6g). Mp 250–251
J ¼ 8.1 Hz, 1H), 7.36–7.16 (m, 5H), 7.08–6.98 (m, 2H), 6.54 (s,
3.1.8 N-((2,4-Dichlorophenyl)(7-hydroxy-2-oxo-4-(triuoro-
300 MHz, CDCl
3
6
ꢀ
1
C; H NMR (300 MHz, CDCl
7.58–7.48 (m, 3H), 7.32 (d, J ¼ 2.1 Hz, 1H), 7.20 (dd, J ¼ 8.5, 2.1
O exchange): d 7.50 (d, J ¼ 8.9 Hz, 1H), 7.38–7.17 (m, 5H), Hz, 1H), 7.02 (d, J ¼ 8.9 Hz, 1H), 6.98 (d, J ¼ 9.1 Hz, 1H), 6.52 (s,
3 6
+ DMSO-d ): d 10.77 (br s, 1H),
1
1
3 6
H), 2.06 (s, 3H) ppm; H NMR (300 MHz, CDCl + DMSO-d )
(D
2
1
3
7
(
1
1
.04 (d, J ¼ 9.4 Hz, 1H), 7.0 (d, J ¼ 9.1 Hz, 1H), 6.55 (s, 1H), 2.08 1H), 2.05 (s, 3H) ppm; C NMR (75 MHz, CDCl
3 6
+ DMSO-d ): d
1
3
2
s, 3H) ppm; C NMR (75 MHz, CDCl + DMSO-d ): d 168.9, 169.2, 160.23, 158.2, 153.7, 141 (q, J ¼ 31.9 Hz), 136.7, 133.0,
3
6
C–F
2
1
59.8, 158.1, 153.0, 140.9 (q, J
¼ 33 Hz), 140.4, 127.7, 126.3, 132.4, 130.5, 128.5, 125.9, 125.2, 121.3 (q, J ¼ 275 Hz), 113.6,
C–F
C–F
1
3
3
25.8, 124.7, 121.1 (q, J ¼ 276 Hz), 114.5, 113.7, 110.7 (q, J
113.4, 110.5 (q, J
C–F
¼ 5.0 Hz), 105.4, 45.2, 22.3 ppm; IR (KBr):
C–F
C–
ꢂ1
F
¼ 4.6 Hz), 105.5, 46.4, 22.6 ppm; IR (KBr): 3414, 1735, 1576, 3367, 2925, 1725, 1575, 1278, 1152, 1078, 866 cm ; HRMS (ESI)
ꢂ1
+
+
1
284, 1145, 826 cm ; HRMS (ESI) anal. calcd for C19
H
15
F
3
NO
4
anal. calcd for C19
467.9991.
2 3 4
H12Cl F NNaO m/z 467.9987 [M + Na] , found
m/z 378.0947 [M + H] , found 378.0957.
3.1.4 N-((7-Hydroxy-2-oxo-4-(triuoromethyl)-2H-chromen-
3.1.9 N-((3,4-Dimethoxyphenyl)(7-hydroxy-2-oxo-4-(triuoro-
8
1
1
-yl)(4-(triuoromethyl)phenyl)methyl) acetamide (6c). Mp methyl)-2H-chromen-8-yl)methyl)acetamide (6h). Mp 150–
ꢀ
1
ꢀ
1
86–187 C; H NMR (300 MHz, CDCl + DMSO-d ): d 11.08 (br s, 152 C; H NMR (300 MHz, CDCl ): d 10.45 (br s, 1H), 7.55 (d, J ¼
3
6
3
H), 7.93 (d, J ¼ 10.1 Hz, 1H), 7.54–7.46 (m, 5H), 7.06 (d, J ¼ 7.5 9.4 Hz, 1H), 7.46 (d, J ¼ 7.4 Hz, 1H), 7.02–6.94 (m, 2H), 6.91–6.83
Hz, 1H), 7.01 (d, J ¼ 10.1 Hz, 1H), 6.55 (s, 1H), 2.07 (s, 3H) ppm; (m, 2H), 6.76 (d, J ¼ 8.5 Hz, 1H), 6.55 (s, 1H), 3.83 (s, 6H), 2.17
1
3
13
3 6 3 6
C NMR (75 MHz, CDCl + DMSO-d ): d 169.0, 159.4, 157.9, (s, 3H) ppm; C NMR (75 MHz, CDCl + DMSO-d ): d 168.8,
2
2
1
52.9, 144.7, 141.0 (q, JC–F ¼ 32.4 Hz), 126.2, 125.0, 124.9, 124.4 159.4, 158.2, 152.9, 148.2, 147.5, 141.1 (q, JC–F ¼ 35.5 Hz), 132.9,
3
1
1
3
(
q, JC–F ¼ 3.8 Hz), 121.1 (q, JC–F ¼ 275.6 Hz), 114.6, 113.6, 110.7 124.5, 121.3 (q, JC–F ¼ 275 Hz), 118.2, 115.5, 113.7, 110.5 (q, JC–F
3
(q, JC–F ¼ 6.0 Hz), 105.6, 46.2, 22.6 ppm; IR (KBr): 3359, 2927, ¼ 5.8 Hz), 110.0, 105.7, 55.3, 55.3, 46.7, 22.8 ppm; IR (KBr): 3364,
ꢂ1
ꢂ1
1
728, 1654, 1579, 1328, 1280, 1148, 869, 675 cm ; HRMS (ESI) 2924, 1724, 1577, 1280, 1142, 1075 cm ; HRMS (ESI) anal. calcd
+
+
anal. calcd for C H F NNaO m/z 468.0641 [M + Na] , found for C H F NNaO m/z 460.0978 [M + Na] , found 460.0977.
2
0
13
6
4
21 18
3
6
468.0641.
3.1.10 N-((4-Fluorophenyl)(7-hydroxy-2-oxo-4-(triuoro-
3
.1.5 N-((7-Hydroxy-2-oxo-4-(triuoromethyl)-2H-chromen- methyl)-2H-chromen-8-yl)methyl)acetamide (6i). Mp 236–237
ꢀ
ꢀ
1
8
-yl)(4-methoxyphenyl)methyl)acetamide (6d). Mp 123–124 C;
C; H NMR (300 MHz, CDCl
): d 7.65 (d, J ¼ 9.2 Hz, 1H), 7.45 (d, J ¼ 1H), 7.54–7.47 (m, 1H), 7.39–7.29 (m, 2H), 7.07–6.91 (m, 4H),
3
+ DMSO-d
6
): d 7.76 (d, J ¼ 9.2 Hz,
1
H NMR (300 MHz, CDCl
.7 Hz, 1H), 7.24 (d, J ¼ 8.7 Hz, 2H), 6.97 (d, J ¼ 8.9 Hz, 1H), 6.90 6.55 (s, 1H), 2.06 (s, 3H) ppm; C NMR (75 MHz, CDCl
): d 169.0, 162.6, 159.6, 159.3, 158.2, 152.9, 141.3 (q,
3
1
3
8
(
3
1
1
1
3
+
d, J ¼ 9.2 Hz, 1H), 6.80 (d, J ¼ 8.7 Hz, 2H), 6.53 (s, 1H), 3.74 (s, DMSO-d
6
1
3
2
1
H), 2.14 (s, 3H) ppm; C NMR (75 MHz, CDCl
3
+ DMSO-d
6
): d
J
C–F ¼ 31.3 Hz), 136.3, 136.2, 127.6, 127.5, 124.8, 121.1 (q, JC–F
2
3
68.7, 159.5, 158.2, 157.9, 152.8, 141.1 (q, JC–F ¼ 32.4 Hz), ¼ 276.5 Hz), 115.2, 114.5, 114.2, 113.7, 110.6 (q, J
¼ 5.5 Hz),
C–F
1
32.2, 127.0, 124.5, 124.5, 121.1 (q, J ¼ 276 Hz), 115.6, 113.7, 105.6, 46.0, 22.6 ppm; IR (KBr): 3414, 3079, 2924, 1737, 1577,
C–F
3
ꢂ1
13.0, 110.6, 110.5 (q, J
¼ 6.0 Hz), 105.6, 54.6, 46.2, 22.7 1286, 1149, 1084, 830 cm ; HRMS (ESI) anal. calcd for
C–F
+
ppm; IR (KBr): 3378, 2928, 1741, 1578, 1511, 1280, 1142, 822
C
19
H
13
F
4
NNaO
4
m/z 418.0672 [M + Na] , found 418.0672.
ꢂ1
+
cm ; ESI (MS): m/z 430 [M + Na] .
3.1.11 N-((7-Hydroxy-2-oxo-4-(triuoromethyl)-2H-chromen-
.1.6 N-((3-Chlorophenyl)(7-hydroxy-2-oxo-4-(triuoromethyl)- 8-yl)(4-isopropylphenyl)methyl)acetamide (6j). Mp 210–211 C;
ꢀ
3
ꢀ
1
1
2
(
1
(
H-chromen-8-yl)methyl)acetamide (6e). Mp 249–250 C; H NMR
300 MHz, CDCl + DMSO-d
): d 10.98 (br s, 1H), 7.75 (d, J ¼ 9.2 Hz, J ¼ 9.1 Hz, 1H), 7.46 (dd, J ¼ 9.1, 2.2 Hz, 1H), 7.24 (d, J ¼ 8.3 Hz,
H), 7.56–7.49 (m, 1H), 7.33 (s, 1H), 7.29–7.15 (m, 3H), 7.08–6.99 2H), 7.15 (d, J ¼ 8.3 Hz, 2H), 6.98 (d. J ¼ 9.1 Hz, 1H), 6.87 (d, J ¼
3 6
H NMR (300 MHz, CDCl + DMSO-d ): d 10.43 (br s, 1H), 7.54 (d,
3
6
13
m, 2H), 6.56 (s, 1H), 2.08 (s, 3H) ppm; C NMR (75 MHz, CDCl + 9.1 Hz, 1H), 6.54 (s, 1H), 2.93–2.79 (m, 1H), 2.15 (s, 3H), 1.20 (d, J
3
2
13
DMSO-d ): d 169.2, 159.7, 158.1, 143.2, 140.8 (q, J
¼ 34 Hz), ¼ 6.8 Hz, 6H) ppm; C NMR (75 MHz, CDCl + DMSO-d ): d
6
C–F
3
6
1
2
1
1
(
33.0, 129.37, 126.3, 125.8, 125.0, 124.5, 121.2 (q, JC–F ¼ 274 Hz), 168.8, 159.5, 158.3, 152.9, 146.9, 140.8 (q, JC–F ¼ 31 Hz), 137.4,
3
1
15.0, 113.6, 111.1 (q, JC–F ¼ 4.3 Hz), 105.4, 45.9, 22.5 ppm; IR 125.8, 125.7, 124.6, 121.1 (q, JC–F ¼ 275 Hz), 115.5, 113.7, 110.5
3
KBr): 3413, 2923, 1745, 1644, 1511, 1400, 1286, 1078, 825, 547 (q, JC–F ¼ 6.0 Hz), 105.7, 46.6, 32.9, 23.4 (2C), 22.8 ppm; IR (KBr):
ꢂ1
ꢂ1
cm ; HRMS (ESI) anal. calcd for C19
H
13ClF
3
NNaO
4
m/z 434.0377 3412, 2964, 1740, 1581, 1282, 1139, 1078 cm ; HRMS (ESI) anal.
+
+
[
M + Na] , found 434.0378.
calcd for C22
H
20
F
3
NNaO
4
m/z 442.1236 [M + Na] , found
3
.1.7 N-((3-Bromophenyl)(7-hydroxy-2-oxo-4-(triuoromethyl)- 442.1237.
ꢀ
1
2
(
(
6
H-chromen-8-yl)methyl)acetamide (6f). Mp 258–259 C; H NMR
3.1.12 N-((7-Hydroxy-2-oxo-4-(triuoromethyl)-2H-chromen-
ꢀ
1
300 MHz, CDCl + DMSO-d ): d 7.82 (d, J ¼ 9.1 Hz, 1H), 7.55–7.48 8-yl)(phenyl)methyl)benzamide (6k). Mp 104–106 C; H NMR
3
6
m, 2H, Ar-H, NH), 7.35–7.25 (m, 2H), 7.17 (d, J ¼ 7.7 Hz, 1H), 7.05– (300 MHz, CDCl
3
+ DMSO-d
6
): d 8.45 (d, J ¼ 9.2 Hz, 1H), 7.87 (d, J
13
.98 (m, 2H), 6.56 (s, 1H), 2.08 (s, 3H) ppm; C NMR (75 MHz, ¼ 7.0 Hz, 2H), 7.57–7.37 (m, 6H), 7.32–7.21 (m, 4H), 7.05 (d, J ¼
2
13
CDCl
3
+ DMSO-d
6
): d 168.9, 159.8, 157.8, 152.9, 143.2, 140.7 (q, JC–F 9.1 Hz, 1H), 6.59 (s, 1H) ppm; C NMR (75 MHz, CDCl
3
+ DMSO-
): d 165.6, 159.6, 158.1, 152.9, 141.0 (q, JC–F ¼ 32.4 Hz), 140.3,
21.4, 121.3 (q, JC–F ¼ 275.6 Hz), 114.7, 113.6, 110.7 (q, JC–F ¼ 5.8 133.8, 132.1, 131.0, 129.0, 128.0, 127.8, 127.7, 126.5, 126.6, 125.9,
2
¼
32.4 Hz), 129.7, 129.3, 129.1, 128.6, 125.9, 124.8, 124.7, 122.9,
d
6
1
3
1
14504 | RSC Adv., 2014, 4, 14501–14506
This journal is © The Royal Society of Chemistry 2014