3984 J ournal of Medicinal Chemistry, 2004, Vol. 47, No. 16
Rao et al.
H-2, H-6), 7.24-7.39 (m, 3H, phenyl H-3, H-4, H-5), 7.41 (d, J
) 8.2 Hz, 2H, 4-methanesulfonylphenyl H-2, H-6), 7.75 (d, J
) 8.2 Hz, 2H, 4-trifluoromethylphenyl H-2, H-6), 7.81 (d, J )
8.2 Hz, 2H, 4-methanesulfonylphenyl H-3, H-5), 8.03 (d, J )
8.2 Hz, 2H, 4-trifluoromethylphenyl H-3, H-5). Anal. (C25H17
F3O4S): C, H.
yphenyl H-2, H-6), 7.86 (d, J ) 8.8 Hz, 2H, methanesulfo-
nylphenyl H-3, H-5). Anal. (C25H19FO5S): C, H.
6-(4-Eth oxyp h en yl)-3-(4-m eth a n esu lfon ylp h en yl)-4-(4-
flu or op h en yl)p yr a n -2-on e (12i). The product was obtained
as a yellow solid by oxidation of 11i in the presence of aqueous
Oxone solution (0.19 g, 75.7%): mp 243-245 °C; IR (film):
1703 (CdO), 1310, 1152 (SO2) cm-1; 1H NMR (CDCl3): δ 1.45
(t, J ) 7.0 Hz, 3H, OCH2CH3), 2.98 (s, 3H, SO2CH3), 4.00 (q,
J ) 7.0 Hz, 2H, OCH2CH3), 6.64 (s, 1H, pyranone H-5), 6.88
(dd, J 3 ) 8.5, J 3 ) 8.5 Hz, 2H, 4-fluorophenyl H-3, H-5),
-
6-(4-Meth oxyp h en yl)-3-(4-m eth a n esu lfon ylp h en yl)-4-
p h en ylp yr a n -2-on e (12e). The product was obtained as a
yellow solid by oxidation of 11e in the presence of aqueous
Oxone solution (0.20 g, 86.2%): mp 218-220 °C; IR (film):
1705 (CdO), 1315, 1157 (SO2) cm-1; 1H NMR (CDCl3): δ 3.03
(s, 3H, SO2CH3), 3.89 (s, 3H, OCH3), 6.77 (s, 1H, pyranone H-5),
6.99 (d, J ) 8.2 Hz, 2H, 4-methoxyphenyl H-3, H-5), 7.12-
7.16 (m, 2H, phenyl H-2, H-6), 7.22-7.38 (m, 3H, phenyl H-3,
H-4, H-5), 7.40 (d, J ) 8.5 Hz, 2H, 4-methanesulfonylphenyl
H-2, H-6), 7.78 (d, J ) 8.2 Hz, 2H, 4-methoxyphenyl H-2, H-6),
7.87 (d, J ) 8.2 Hz, 2H, 4-methanesulfonylphenyl H-3, H-5);
13C NMR (CDCl3): δ 44.5 (SO2CH3), 55.5 (OCH3), 103.5
(pyranone C-5), 114.4 (4-methoxyphenyl C-3, C-5), 119.5
(pyranone C-3), 123.1 (4-methoxyphenyl C-1), 126.9 (phenyl
C-3, C-5), 128.5, 128.5 and 128.7 (4-methoxyphenyl C-2, C-6;
4-methanesulfonylphenyl C-2, C-6; phenyl C-2, C-6), 129.2
(phenyl C-4), 131.9 (4-methanesulfonylphenyl C-3, C-5), 137.0
(phenyl C-1), 139.0 (4-methanesulfonylphenyl C-1), 140.1 (4-
methanesulfonylphen
HH
FH
6.90 (d, J ) 8.8 Hz, 2H, 4-ethoxyphenyl H-3, H-5), 7.07 (dd,
J 3 ) 8.5, J 4 ) 5.2 Hz, 2H, 4-fluorophenyl H-2, H-6), 7.31
HH
FH
(d, J ) 9.0 Hz, 2H, 4-methanesulfonylphenyl H-2, H-6), 7.73
(d, J ) 8.8 Hz, 2H, 4-ethoxyphenyl H-2, H-6), 7.77 (d, J ) 9.0
Hz, 2H, 4-methanesulfonylphenyl H-3, H-5). Anal. (C26H21
FO5S): C, H.
-
6-(4-Me t h a n e su lfon ylp h e n yl)-3,4-d ip h e n ylp yr a n -2-
on e (12j). The product was obtained as a yellow solid by
oxidation of 11j in the presence of aqueous Oxone solution
(0.18 g, 82.8%): mp 178-180 °C; IR (film): 1716 (CdO), 1306,
1
1159 (SO2) cm-1; H NMR (CDCl3): δ 3.12 (s, 3H, SO2CH3),
6.97 (s, 1H, pyranone H-5), 7.16-7.39 (m, 10H, phenyl H-2,
H-3, H-4, H-5, H-6), 8.07 (d, J ) 8.8 Hz, 2H, 4-methanesulfo-
nylphenyl H-2, H-6), 8.10 (d, J ) 8.8 Hz, 2H, 4-methanesulfo-
nylphenyl H-3, H-5). Anal. (C24H18O4S): C, H.
4-(4-Me t h a n e su lfon ylp h e n yl)-3,6-d ip h e n ylp yr a n -2-
on e (12k ). The product was obtained as a yellow solid by
oxidation of 11k in the presence of aqueous Oxone solution
(0.16 g, 76.3%): mp 188-190 °C; IR (film): 1723 (CdO), 1315,
yl C-4), 154.7 (pyranone C-4), 159.5 (4-methoxyphenyl C-4),
161.9 (pyranone C-6), 162.1 (pyranone C-2). Anal. (C25H20
O5S): C, H.
-
6-(4-Ethoxyphenyl)-3-(4-methanesulfonylphenyl)-4-phen-
ylp yr a n -2-on e (12f). The product was obtained as a yellow
solid by oxidation of 11f in the presence of aqueous Oxone
solution (0.18 g, 78.5%): mp 250-252 °C; IR (film): 1698 (Cd
1
1157 (SO2) cm-1; H NMR (CDCl3): δ 3.05 (s, 3H, SO2CH3),
6.78 (s, 1H, pyranone H-5), 7.15-7.18 (m, 2H, phenyl H-2,
H-6), 7.21-7.26 (m, 3H, phenyl H-3, H-4, H-5), 7.37 (d, J )
8.5 Hz, 2H, 4-methanesulfonylphenyl H-2, H-6), 7.48-7.52 (m,
3H, phenyl H-3, H-4, H-5), 7.86 (d, J ) 8.5 Hz, 2H, 4-meth-
anesulfonylphenyl H-3, H-5), 7.90-7.93 (m, 2H, phenyl H-2,
H-6). Anal. (C24H18O4S): C, H.
1
O), 1313, 1142 (SO2) cm-1; H NMR (CDCl3): δ 1.44 (t, J )
7.0 Hz, 3H, OCH2CH3), 3.03 (s, 3H, SO2CH3), 4.08 (q, J ) 7.0
Hz, 2H, OCH2CH3), 6.77 (s, 1H, pyranone H-5), 6.97 (d, J )
8.8 Hz, 2H, 4-ethoxyphenyl H-3, H-5), 7.11-7.14 (m, 2H,
phenyl H-2, H-6), 7.25-7.31 (m, 3H, phenyl H-3, H-4, H-5),
7.39 (d, J ) 8.2 Hz, 2H, 4-methanesulfonylphenyl H-2, H-6),
7.78 (d, J ) 8.2 Hz, 2H, 4-ethoxyphenyl H-2, H-6), 7.85 (d, J
) 8.2 Hz, 2H, 4-methanesulfonylphenyl H-3, H-5); 13C NMR
(CDCl3): δ 14.7 (OCH2CH3), 44.5 (SO2CH3), 63.8 (OCH2CH3),
103.4 (pyranone C-5), 114.9 (4-ethoxyphenyl C-3, C-5), 119.4
(pyranone C-3), 123.2 (4-ethoxyphenyl C-1), 126.9 (phenyl C-3,
C-5), 128.5, 128.5, and 128.7 (4-ethoxyphenyl C-2, C-6; 4-meth-
anesulfonylphenyl C-2, C-6; phenyl C-2, C-6), 129.2 (phenyl
C-4), 132.0 (4-methanesulfonylphenyl C-3, C-5), 137.0 (phenyl
C-1), 139.0 (4-methanesulfonylphenyl C-1), 140.1 (4-methane-
sulfonylphenyl C-4), 154.7 (pyranone C-4), 159.6 (4-ethoxyphen-
yl C-4), 161.5 (pyranone C-6), 162.1 (pyranone C-2). Anal.
(C26H22O5S): C, H.
6-(4-Methylphenyl)-4-(4-methanesulfonylphenyl)-3-phen-
ylp yr a n -2-on e (12l). The product was obtained as a oil by
oxidation of 11l in the presence of aqueous Oxone solution
(0.17 g, 78.7%): IR (film): 1695 (CdO), 1317, 1148 (SO2) cm-1
;
1H NMR (CDCl3): δ 2.44 (s, 3H, CH3), 3.05 (s, 3H, SO2CH3),
6.74 (s, 1H, pyranone H-5), 7.12-7.17 (m, 2H, phenyl H-2,
H-6), 7.18-7.31 (m, 3H, phenyl H-3, H-4, H-5), 7.34 (d, J )
8.4 Hz, 2H, 4-methylphenyl H-3, H-5), 7.37 (d, J ) 8.2 Hz,
2H, 4-methanesulfonylphenyl H-2, H-6), 7.79 (d, J ) 8.2 Hz,
2H, 4-methylphenyl H-2, H-6), 7.82 (d, J ) 8.2 Hz, 2H,
4-methanesulfonylphenyl H-3, H-5). Anal. (C25H20O4S): C, H.
6-(4-Eth ylph en yl)-4-(4-m eth an esu lfon ylph en yl)-3-ph en -
ylp yr a n -2-on e (12m ). The product was obtained as a yellow
solid by oxidation of 11m in the presence of aqueous Oxone
solution (0.19 g, 85%): mp 173-175 °C; IR (film): 1709 (Cd
1
O), 1315, 1157 (SO2) cm-1; H NMR (CDCl3): δ 1.26 (t, J )
6-(4-Fluorophenyl)-3-(4-methanesulfonylphenyl)-4-phen-
ylp yr a n -2-on e (12g). The product was obtained as a yellow
solid by oxidation of 11g in the presence of aqueous Oxone
solution (0.18 g, 79.6%): mp 294-296 °C; IR (film): 1709 (Cd
7.6 Hz, 3H, CH2CH3), 3.05 (s, 3H, SO2CH3), 2.71 (q, J ) 7.6
Hz, 2H, CH2CH3), 6.74 (s, 1H, pyranone H-5), 7.18-7.25 (m,
5H, phenyl H-2, H-3, H-4, H-5, H-6), 7.26 (d, J ) 8.5 Hz, 2H,
4-ethylphenyl H-3, H-5), 7.37 (d, J ) 8.2 Hz, 2H, 4-methane-
sulfonylphenyl H-2, H-6), 7.82-7.86 (m, 4H, 4-methanesulfo-
1
O), 1320, 1145 (SO2) cm-1; H NMR (CDCl3): δ 3.04 (s, 3H,
SO2CH3), 6.82 (s, 1H, pyranone H-5), 7.12-7.14 (m, 2H, phenyl
H-2, H-6), 7.15 (dd, J 3 ) 8.2, J 3 ) 8.2 Hz, 2H, 4-fluorophen-
HH
FH
nylphenyl H-3, H-5; 4-ethylphenyl H-2, H-6). Anal. (C26H22
O4S): C, H.
-
yl H-3, H-5), 7.20-7.35 (m, 3H, phenyl H-3, H-4, H-5), 7.40
(d, J ) 8.2 Hz, 4-methanesulfonylphenyl H-2, H-6), 7.80 (d, J
6-(4-Tr iflu or om eth ylph en yl)-4-(4-m eth an esu lfon ylph en -
yl)-3-p h en ylp yr a n -2-on e (12n ). The product was obtained
as a yellow solid by oxidation of 11n in the presence of aqueous
Oxone solution (0.19 g, 75.4%): mp 203-205 °C; IR (film):
1705 (CdO), 1315, 1145 (SO2) cm-1; 1H NMR (CDCl3): δ 3.05
(s, 3H, SO2CH3), 6.86 (s, 1H, pyranone H-5), 7.14-7.19 (m,
2H, phenyl H-2, H-6), 7.23-7.35 (m, 3H, phenyl H-3, H-4, H-5),
7.38 (d, J ) 8.8 Hz, 2H, 4-methanesulfonylphenyl H-2, H-6),
7.74 (d, J ) 8.5 Hz, 2H, 4-trifluoromethylphenyl H-2, H-6),
7.77 (d, J ) 8.8 Hz, 2H, 4-methanesulfonylphenyl H-3, H-5),
8.01 (d, J ) 8.5 Hz, 2H, 4-trifluoromethylphenyl H-3, H-5).
Anal. (C25H17F3O4S): C, H.
) 8.2 Hz, 4-methanesulfonylphenyl H-3, H-5), 7.91 (dd, J 3
HH
) 8.2, J 4 ) 5.2 Hz, 2H, 4-fluorophenyl H-2, H-6). Anal.
FH
(C24H17FO4S): C, H.
6-(4-Meth oxyp h en yl)-3-(4-m eth a n esu lfon ylp h en yl)-4-
(4-flu or op h en yl)p yr a n -2-on e (12h ). The product was ob-
tained as a yellow solid by oxidation of 11h in the presence of
aqueous Oxone solution (0.21 g, 88%): mp 224-226 °C; IR
(film): 1709 (CdO), 1315, 1158 (SO2) cm-1; 1H NMR (CDCl3):
δ 3.04 (s, 3H, SO2CH3), 3.88 (s, 3H, OCH3), 6.73 (s, 1H,
pyranone H-5), 6.95 (dd, J 3
) 8.5, J 3
) 8.5 Hz, 2H,
HH
FH
4-fluorophenyl H-3, H-5), 6.97 (d, J ) 8.2 Hz, 2H, 4-methoxy-
phenyl H-3, H-5), 7.09 (dd, J 3 ) 8.5, J 4 ) 5.2 Hz, 2H,
6-(4-Meth oxyp h en yl)-4-(4-m eth a n esu lfon ylp h en yl)-3-
p h en ylp yr a n -2-on e (12o). The product was obtained as a
yellow solid by oxidation of 11o in the presence of aqueous
HH
FH
4-fluorophenyl H-2, H-6), 7.39 (d, J ) 8.8 Hz, 2H, 4-methane-
sulfonylphenyl H-2, H-6), 7.81 (d, J ) 8.2 Hz, 2H, 4-methox-