Med Chem Res
0 0 0 0 0 0 0
(E)-1-(6 -Hydroxy-1 ,3 -dimethyl-1 ,2 ,3 ,4 -tetrahydro-
1
,673, 1,718 (3 9 C=O), 2,925 (C–H) and 3,420 (–OH);
1
0 0 0 00
H NMR (400 MHz, DMSO-d ): d 2.37 (3H, s, –CH ),
3
2 ,4 -dioxopyrimidin-5 -yl)-3-[-p-{(1 -(phenyl)-1H-
1 ,2 ,3 -triazol-4 -yl)methoxy}phenyl]-prop-2-ene-1-
one (7d)
6
3
0
0
00 00
00
.20 (6H, s, N–CH ), 5.32 (2H, s, –OCH ), 6.97 (1H, d,
3
2
J = 8.8 Hz, ArH), 7.22 (2H, d, J = 8.8 Hz, ArH), 7.39
(
(
(
2H, d, J = 8.08 Hz, ArH), 7.72–7.79 (3H, m, ArH), 7.98
1H, d, J = 16.1 Hz), 8.39 (1H, d, J = 15.4 Hz) and 8.92
The product 7d was obtained as described earlier in the
general procedure from 4d (200 mg, 1 mmol) and 5
(141 mg, 1 mmol) as a yellow solid. Yield = 56.4 %;
1
3
1H, s); C NMR (100 MHz, DMSO-d ): d 20.63, 27.47,
6
6
1
1
1.11, 77.37, 96.04, 113.25, 114.78, 115.73, 117.07,
17.41, 119.90, 128.02, 130.26, 131.03, 134.06, 143.15,
53.72, 161.50, 181.71 and 206.86; Anal. calcd. for
-
1
m.p. = 238–240 °C; IR mmax (cm ) = 1,173 (C–O),
1,592, 1,660, 1,714 (3 9 C=O), 2,945 (C–H) and 3,656 (–
1
C H N O : C, 63.42, H, 4.90, N, 14.79, Found: C, 63.32,
2
?
H, 4.95, N, 14.80; ESI–MS m/z: [M-H] = 474.4.
OH); H NMR (400 MHz, DMSO-d
6
): d 3.27 (6H, s, N–
), 7.17 (2H, d, J = 8.8 Hz, ArH),
.43–7.51 (1H, m, ArH), 7.55–7.59 (2H, m, ArH), 7.70
5 23 5 5
CH ), 5.30 (2H, s, –OCH
3 2
7
0
0
0
0
0
0
0
(
E)-1-(6 -Hydroxy-1 ,3 -dimethyl-1 ,2 ,3 ,4 -tetrahydro-
0
(2H, d, J = 8.08 Hz, ArH), 7.87 (2H, d, J = 8.04 Hz,
ArH), 7.90 (1H, d, J = 16.11 Hz), 8.35 (1H, d,
0 0 00
2
,4 -dioxopyrimidin-5 -yl)-3-[-p-{(1 -(p-methoxy
0
0
00 00
00
13
J = 16.1 Hz) and 8.94 (1H, s); C NMR (100 MHz,
phenyl)-1H-1 ,2 ,3 -triazol-4 -yl)methoxy}phenyl]-
prop-2-ene-1-one (7b)
DMSO-d
23.07, 124.45, 129.16, 130.29, 131.41, 136.87, 143.32,
152.94, 155.04, 169.79, 188.68 and 210.62; Anal. calcd. for
: C, 62.74, H, 4.61, N, 15.24, Found: C, 62.89,
): d 25.30, 61.25, 79.04, 94.74, 119.86, 120.42,
6
1
The product 7b was obtained as described earlier in the
general procedure from 4b (200 mg, 1 mmol) and 5
C H N O
24 21 5 5
?
(
122 mg, 1 mmol) as a light green solid. Yield = 51.6 %;
-
m.p. = 298–300 °C; IR mmax (cm ) = 1,172 (C–O),
,651, 1,690, 1,717 (3 9 C=O), 2,936 (C–H) and 3,663 (–
H, 4.55, N, 15.78; ESI–MS m/z: [M-H] = 458.4.
1
0 0 0 0 0 0 0
(E)-1-(6 -Hydroxy-1 ,3 -dimethyl-1 ,2 ,3 ,4 -tetrahydro-
1
1
0 0 0 00
OH); H NMR (400 MHz, DMDO-d ): d 3.09 (6H, s, N–
CH ), 3.81 (3H, s, –OCH ) 5.24 (2H, s, –OCH ), 7.07–7.13
3
2 ,4 -dioxopyrimidin-5 -yl)-3-[-p-{(1 -(m-methoxy
phenyl)-1H-1 ,2 ,3 -triazol-4 -yl)methoxy}phenyl]-
prop-2-ene-1-one (7e)
6
0
0
00 00
00
3
2
(
(
4H, m, ArH), 7.48 (2H, d, J = 8.8 Hz, ArH), 7.79–7.81
1
4H, m) and 8.84 (1H, s); C NMR (100 MHz, DMSO-
3
d6): d 27.13, 55.57, 61.30, 77.56, 96.08, 114.89, 115.09,
The product 7e was obtained as described earlier in the
general procedure from 4e (200 mg, 1 mmol) and 5
(122 mg, 1 mmol) as a yellow solid. Yield = 57.9 %;
1
21.85, 122.92, 128.98, 129.31, 129.99, 134.96, 143.48,
1
58.53, 159.34, 163.40, 186.85 and 207.42; Anal. calcd. for
-
1
C H N O : C, 61.34, H, 4.74, N, 14.31, Found: C, 61.66,
2
m.p. = 179–180 °C; IR mmax (cm ) = 1,172 (C–O),
1,590, 1,673, 1,710 (3 9 C=O), 2,939 (C–H) and 3,418 (–
5 23 5 6
?
H, 4.41, N, 14.72; ESI–MS m/z: [M-H] = 490.4.
1
OH); H NMR (400 MHz, DMSO-d ) : d 3.17 (6H, s, N–
6
0
0
0
0
0
0
00
0
0
(
E)-1-(6 -Hydroxy-1 ,3 -dimethyl-1 ,2 ,3 ,4 -tetrahydro-
CH ), 3.83 (3H, s, –OCH ), 5.30 (2H, s, –OCH ), 7.04 (1H,
3 3 2
0
0
2
1
1
,4 -dioxopyrimidin-5 -yl)-3-[-p-{(1 -(p-flourophenyl)-
0
d, J = 5.84 Hz, ArH), 7.17 (2H, d, J = 8.04 Hz, ArH),
7.42–7.47 (3H, m, ArH), 7.69 (2H, d, J = 8.08 Hz, ArH),
7.93 (1H, d, J = 16.1 Hz), 8.35 (1H, d, J = 15.4 Hz) and
0
00 00
00
H-1 ,2 ,3 -triazol-4 -yl)methoxy}phenyl]-prop-2-ene-
-one (7c)
1
3
8
.98 (1H, s); C NMR (100 MHz, DMSO-d ): d 27.92,
6
The product 7c was obtained as described earlier in the
general procedure from 4c (200 mg, 1 mmol) and 5 (133
29.24, 56.08, 60.98, 79.34, 94.24, 106.00, 112.21, 114.65,
115.83, 117.91, 122.82, 127.59, 130.99, 132.47, 137.77,
143.63, 145.70, 150.09, 160.27, 163.65, 182.38 and
mg, 1 mmol) as
m.p. = 258–259 °C; IR mmax (cm ) = 1,172 (C–O),
,593, 1,660, 1,714 (3 9 C=O), 2,947 (C–H) and 3,674 (–
a yellow solid. Yield = 51.1 %;
-
1
204.32; Anal. calcd. for C25H N O : C, 61.34, H, 4.74, N,
23 5 6
1
14.31, Found: C, 61.61, H, 4.75, N, 14.12; ESI–MS m/z:
?
[M-H] = 488.4.
1
OH); H NMR (400 MHz, DMSO-d ): d 3.21 (6H, s, N–
6
CH ), 5.33 (2H, s, –OCH ), 7.21 (2H, d, J = 8.8 Hz, ArH),
3
2
0 0 0 0 0 0 0
(E)-1-(6 -Hydroxy-1 ,3 -dimethyl-1 ,2 ,3 ,4 -tetrahydro-
7
.47 (2H, d, J = 8.8 Hz, ArH), 7.74 (2H, d, J = 8.7 Hz,
ArH), 7.94–8.00 (3H, m), 8.40 (1H, d, J = 16.1 Hz) and
0
0
0
00
2 ,4 -dioxopyrimidin-5 -yl)-3-[-p-{(1 -(m-tolylphenyl)-
00 00 00
1
3
00
8
6
1
1
.97 (1H, s); C NMR (100 MHz, DMSO-d ): d 27.66,
1H-1 ,2 ,3 -triazol-4 -yl)methoxy}phenyl]-prop-2-ene-
1-one (7f)
6
6.77, 79.26, 94.19, 113.48, 115.55, 116.51, 117.08,
22.57, 122.94, 127.66, 130.87, 144.49, 154.13, 161.11,
68.72, 173.45, 188.15 and 205.38; Anal. calcd. for
The product 7f was obtained as described earlier in the general
procedure from 4f (100 mg, 1 mmol) and 5 (67 mg, 1 mmol)
as a yellow solid. Yield = 51 %; m.p. = 257–259 °C; IR
C H FN O : C, 60.37, H, 4.22, N, 14.67, Found: C,
2
4
20
5 5
?
0.60, H, 4.36, N, 14.53; ESI–MS m/z: [M-H] = 478.4.
6
1
23