Med Chem Res
0
0
0
imidazole), 6.74 (s, 1H, H-8), 6.72 (s, 1H, H-3), 6.28 (s,
127.6 (CH, C-4 ), 127.2 (2CH, C-2 , C-6 ), 124.4 (CH,
1
H, H-6), 4.71 (s, 2H, CH2); C NMR (DMSO-d6,
3
1
C-5¢¢¢), 115.8 (CH, C-3¢¢¢), 104.5 (CH, C-3), 104.2 (C,
C-10), 98.5 (CH, C-6), 92.3 (CH, C-8), 66.9 (CH , C-2 );
?
ESI–MS: m/z 389.11 [M?H] . Anal. Calcd. for
0
0
00
100 MHz): d = 182.5 (C, C-4, C=O), 169.3 (C, C-3 ,
C=O), 164.1 (C,C-7), 163.6 (C,C-2), 161.8 (C, C-5), 158.3
2
0
0
(
C, C-9), 151.8 (C, C-2¢¢¢), 130.9 (C, C-1 ), 128.6 (2C, C-3 ,
C-5 ), 127.9 (CH, C-4 ), 127.6 (2CH, C-4 , C-5 ), 127.1
C H N O (388.37), C, 68.04, H, 4.15; N, 7.21. Found:
2 16 2 5
2
0
0
00
00
C,68.12, H, 4.2; N, 7.09.
0 0
(
(
2CH, C2 , C-6 ), 104.6 (CH, C-3), 104.1 (C, C-10), 98.2
00
CH, C-6), 92.8 (CH-C-8), 66.8 (CH , C-2 ); ESI–MS: m/z
2
?
80.12 [M?H] . Anal. Calcd. for C H N O (379.37):
2-(5-Hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)-N-
3
(pyridin-4-yl)acetamide (13f): colourless solid
2
0 17 3 5
C, 63.32; H, 4.52; N, 11.08. Found: C, 63.47; H, 4.76; N,
1
0.99.
The residue was purified by column chromatography
(petroleum ether/EtOAc); yield: 92 %; IR (KBr) mmax 3,333
2
-(5-Hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)-N-
(OH), 3,190 (NH, amide), 1,725 (C=O, C-4), 1,640 (C=O,
(
thiazol-2-yl)acetamide (13d): colourless solid
amide), 1,565 (C=N, pyridine), 1,520 (C–N, amide), 1,310
-
1
1
(C–N, pyridine) cm
;
H NMR (CDCl , 400 MHz):
3
The residue was purified by column chromatography
d = 11.88 (s, 1H, OH), 10.01 (s, 1H, NH), 8.85 (d, 2H,
J = 8.11 Hz, pyridine), 7.94 (d, 2H, J = 8.45 Hz, pyridine),
7.78–7.43 (5H, m, 2-phenyl), 6.74 (s, 1H, H-8), 6.71 (s, 1H,
(petroleum ether/EtOAc); yield: 88 %; IR (KBr) mmax 3,455
(OH), 3,190 (NH amide), 1,700 (C=O, C-4), 1,655 (C=O,
1
3
amide), 1,520 (C=N, thiazole), 1,522 (C–N, amide), 1,075
1
H-3), 6.29 (d, 1H, J = 7.55 Hz, H-6), 4.48 (s, 2H, CH2);
C
-
1
; H NMR
(
N = C–S–C=N), 680 (C–S, thiazole) cm
NMR (CDCl , 100 MHz): 182.1 (C, C-4, C=O), 167.3 (C,
3
0
0
(
CDCl , 400 MHz,): d = 12.51 (s, 1H, NH), 11.91 (s, 1H,
C-3 , C=O), 164.2 (C, C-7), 163.6 (C, C-2), 161.2 (C, C-5),
3
OH), 7.72–7.45 (5H, m, 2-phenyl), 7.43 (d, 1H,
J = 7.98 Hz, H-4 thiazole), 7.29 (d, 1H, J = 7.45 Hz, H-5
thiazole), 6.75 (s, 1H, H-8), 6.70 (s, 1H, H-3), 6.32 (s, 1H,
158.8 (C, C-9), 155.3 (CH, C-4¢¢¢), 150.8 (2CH, C-2¢¢¢, C-6¢¢¢),
130.3 (C, C-1 ), 128.5 (2CH, C-3 , C-5 ), 127.8 (CH, C-4 ,
0
0
0
0
0
0
127. 4 (2CH, C-2 , C-6 ), 109.4 (2CH, C-3¢¢¢, C-5¢¢¢), 104.9
(CH, C-3), 104.1 (C, C-10), 98.5 (CH, C-6), 92.6 (CH, C-8),
1
3
H-6), 4.89 (s, 2H, CH2); C NMR (CDCl , 100 MHz):
3
00
00
?
66.7 (CH , C-2 ); ESI–MS: m/z 389.11 [M?H] . Anal.
1
82.4 (C, C-4, C=O), 169.7 (C, C-3 , C=O), 164.0 (C,
2
C-7), 163.8 (C, C-2), 162.9 (C, C-2¢¢¢), 161.3 (C, C-5),
Calcd. for C H N O (388.37): C, 68.04, H, 4.15, N, 7.21.
22 16 2 5
0
1
58.8 (C, C-9), 132.3(CH, C-4¢¢¢), 130.2 (C, C-1 ), 128.7
2CH, C-3 , C-5 ), 127.9 (CH, C-4 ), 127.3 (2CH, C-2 ,
Found: C, 68.61, H, 4.67, N, 7.77.
0
0
0
0
(
0
C-6 ), 112.3 (CH, C-3¢¢¢), 105.9 (CH, C-3), 104.1 (C, C-10),
2-(5-Hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)-N-(2-
oxo-2-(pyridin-2-yl)ethyl)acet amide (13g): colourless
solid
00
8.2 (CH, C-6), 92.8 (CH, C-8), 66.8 (CH , C-2 ); ESI–
2
9
?
MS: m/z 395.07 [M?H] . Anal. Calcd. for C H N O S
20 14 2 5
(
394.40): C, 60.91, H, 3.58; N, 7.10; S, 8.13. Found: C,
6
0.99, H, 3.61, N, 7.21, S, 8.02.
The residue was purified by column chromatography
(petroleum ether/EtOAc); yield: 71 %; IR (KBr) mmax IR
2
-(5-Hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)-N-
(KBr) mmax 3,555 (OH), 3,220 (NH, amide), 1,723 (C=O,
C-4), 1,680 (C=O, INH), 1,655 (C=O, amide), 1,565 (C=N,
pyridine), 1,520 (C–N, amide), 1,325 (C–N, pyridine)
(
pyridin-2-yl)acetamide (13e): colourless solid
-
1
1
The residue was purified by column chromatography
petroleum ether/EtOAc); yield: 95 %; IR (KBr) mmax
,390, (OH), 3,210 (NH amide), 1,690 (C=O, C-4), 1,645
C=O, amide), 1,570 (C=N, pyridine), 1,525 (C–N, amide),
cm . H NMR (CDCl , 400 MHz): d = 11.85 (s, 1H,
3
(
OH), 9.07 (s, 1H, NH), 8.85 (d, 2H, J = 8.11 Hz, pyri-
dine), 7.94 (d, 2H, J = 8.45 Hz, pyridine), 7.78–7.43 (5H,
m, 2-phenyl), 6.74 (s, 1H, J = 7.71 Hz, H-8), 6.71 (s, 1H,
J = 7.23 Hz, H-3), 6.29 (d, 1H, J = 7.55 Hz, H-6), 4.48
3
(
-
1
1
H
1
4
8
,320 (C–N, pyridine) cm
;
NMR (CDCl3,
1
3
00 MHz,): d = 11.87 (s, 1H, OH), 10.08 (s, 1H, NH),
.55 (d, 1H, J = 8.34 Hz, H-6 pyridine), 8.21 (d, 1H,
(s, 2H, CH ), 4.45 (s, 2H, CH ); C NMR (CDCl3,
2 2
0
0
100 MHz,): d = 182.4 (C, C-4, C=O), 168.9 (C, C-3 ,
C=O), 164 (C, C-7), 163.6 (C, C-2), 161.4 (C, C-5), 158.4
(C, C-9), 151 (2CH, C-2¢¢¢, C-6¢¢¢), 142.3 (CH, C-4¢¢¢), 130.6
J = 8.34 Hz, H-3 pyridine), 8.05 (t, 1H, J = 8.22 Hz, H-4
pyridine), 7.78–7.43 (5H, m, 2-phenyl), 7.25 (t, 1H,
J = 7.56 Hz, H-5 pyridine), 6.74 (s, 1H, H-8), 6.73 (s, 1H,
0
0
0
0
(C, C-1 ), 128.5 (2CH, C-2 , C-6 ), 127.6 (CH, C-4 ), 126.9
1
3
0
0
H-3), 6.28 (s, 1H, H-6), 4.65 (s, 2H, CH2); C NMR
0
(2CH, C2 , C-6 ), 119.9 (2CH, C-3¢¢¢, C-5¢¢¢), 104.8 (CH,
C-3), 104.2 (C, C-10), 98.1 (CH, C-6), 92.8 (CH, C-8), 66.8
0
(
CDCl , 100 MHz): 182.7 (C, C-4, C=O), 169.3 (C, C-3 ,
3
0
0
?
(CH , C-2 ); ESI–MS: m/z 431.12 [M?H] . Anal. Calcd.
C=O), 164.0 (C, C-7), 163.3 (C, C-2), 161.4 (C, C-5),
2
1
58.4 (C, C-9), 151.8 (C, C-2¢¢¢), 146.7 (CH, C-6¢¢¢), 138.7
for C H N O (430.41): C, 66.97, H, 4.22, N, 6.51.
24 18 2 6
0
0
0
(
CH, C-4¢¢¢), 130.1 (C, C-1 ), 128.6 (2CH, C-3 , C-5 ),
Found: C, 66.91, H, 4.35, N, 6.67.
1
23