Vol. 24, No. 10, 2013
Fozooni et al.
1651
9
6%. Filtered nanoparticles were washed twice with
CH ); 7.29 (dd, 1H, J 4.9, 3.9 Hz, thienyl); 7.66 (s, 1H,
3
dichloromethane, dried and reused without any significant
deactivation even after five runs.
vinyl); 7.96 (d, 1H, J 5 Hz, ArH); 8.13 (d, 1H, J 8.5 Hz,
13
thienyl); C NMR (126 MHz, DMSO-d ) d 11.9, 115.0,
6
1
29.3, 136.9, 139.6, 140.0, 141.9, 161.1, 169.1; MS m/z 193
+
3
-Methyl-4-(1-phenylmethylidene)-5-isoxazolone (3a,
(100%, M ), 135 (32%), 108 (18%); CHN (C H NO S) calc.
9
7
2
C H NO )
(%) C (55.96), H (3.62), N (7.25); found (%) C (55.85),
H (3.57), N (7.39).
1
1
9
2
-1
Yellow crystal; mp 144-145 ºC; IR (KBr) ν/cm 1753,
1
1
7
636; H NMR (500 MHz, DMSO-d ) d 2.32 (s, 3H, CH );
6
3
.47 (s, 1H, vinyl); 7.53 (dd, 2H, J 7.6, 7.4 Hz, ArH); 7.61
4-[1-(4-Fluorophenyl)methylidene]-3-methyl-5-isoxazolone
(
dd, 1H, J 7.4, 7.4 Hz, ArH); 8.37 (d, 2H, J 7.5 Hz, ArH);
(3f, C H NO F)
11
8
2
1
3
-1
C NMR (126 MHz, DMSO-d ) d 12.0, 120.0, 129.4,
Yellow crystal; mp 139-140 ºC; IR (KBr) ν/cm
6
1
1
32.7, 134.2, 134.4, 150.5, 161.7, 168.3; MS m/z 187 (68%,
+
1727, 1623; H NMR (500 MHz, DMSO-d ) d 2.31 (s,
6
M ), 186 (100%), 128 (85%), 90 (65%).
3H, CH ); 7.24 (dd, 2H, J 8.5, 8.5 Hz, ArH); 7.42 (s, 1H,
3
1
3
vinyl); 8.47 (dd, 2H, J 8.38, 5.58 Hz, ArH); C NMR
(126 MHz, DMSO-d ) d 12.0, (116.8, 117.0 J 22.01 Hz),
2
4
5
-{1-[4-(Dimethylamino)phenyl]methylidene}-3-methyl-
6
CF
-isoxazolone (3b, C H N O )
119.6, 129.29, 137.1, 137.2, 148.7, 161.5, (167.4, 168.4
13
14
2
2
-1
1
+
Red crystal; mp 208-209 ºC; IR (KBr) ν/cm 1729,
J 131.05 Hz); MS m/z 205 (100%, M ), 146 (78%), 147
CF
1
1
636; H NMR (500 MHz, DMSO-d ) d 2.26 (s, 3H,
(54%), 108 (39%), 120 (35%); CHN (C H NO F) calc.
11 8 2
6
CH ); 3.17 (s, 6H, 2CH ); 6.73 (d, 2H, J 9.2 Hz, ArH);
(%) C (64.41), H (3.90), N (6.83); found (%) C (64.28),
H (3.85), N (6.75).
3
3
1
3
7.23 (s, 1H, vinyl); 8.42 (d, 2H, J 8.5 Hz, ArH); C NMR
(
1
126 MHz, DMSO-d ) d 12.1, 40.5, 111.6, 111.9, 121.9,
38.0, 149.6, 154.7, 162.0, 170.5; MS m/z 230 (100%, M ),
6
+
3-Phenyl-4-(1-phenylmethylidene)-5-isoxazolone (3g,
2
15 (6%), 172 (11%), 144 (31%); CHN (C H N O ) calc.
C H NO )
13
14
2
2
16 11
2
-1
(
%) C (67.84), H (6.08), N (12.17); found (%) C (67.71),
Yellow crystal; mp 193-194 ºC; IR (KBr) ν/cm 1753,
1
H (5.94), N (12.33).
1636; H NMR (500 MHz, DMSO-d ) d 7.29 (dd, 2H,
6
J 7.7, 7.5 Hz, ArH); 7.76-7.66 (m, 7H, vinyl, ArH), 8.37
1
3
4
5
-[1-(4-Methoxyphenyl)methylidene]-3-methyl-
(d, 2H, J 7.6 Hz, ArH); C NMR (126 MHz, DMSO-d )
6
-isoxazolone(3c, C H NO )
d 119.2, 127.8, 129.2, 129.4, 129.7, 131.5, 132.8, 134.4,
134.6, 153.2, 164.4, 168.5; MS m/z 249 (100%, M ), 205
(57%), 191 (65%), 102 (100%).
12
11
3
-1
+
Yellow crystal; mp 160-161 ºC; IR (KBr) ν/cm 1753,
1
1
3
612; H NMR (500 MHz, DMSO-d ) d 2.32 (s, 3H, CH );
.96 (s, 3H, OCH ); 7.05 (d, 2H, J 9 Hz, ArH); 7.38 (s, 1H,
6
3
3
13
vinyl); 8.47 (d, 2H, J 9 Hz, ArH); C NMR (126 MHz,
4-{1-[4-(Dimethylamino)phenyl]methylidene}-3-phenyl-
DMSO-d ) d 12.1, 56.1, 115.1 116.8, 126.3, 137.4, 149.7,
5-isoxazolone (3h, C H N O )
6
18 16
2
2
+
-1
1
1
61.7, 165.0, 169.2; MS m/z 217 (100%, M ), 202 (8%),
59 (28%).
Red crystal; mp 142-143 ºC IR (KBr) ν/cm 1729,
1
1636; H NMR (500 MHz, DMSO-d ) d 3.19 (s, 6H,
6
2
CH ); 6.74 (d, 2H, J 9.2 Hz, ArH); 7.41 (s, 1H, vinyl);
3
3
5
-Methyl-4-[1-(4-methylphenyl)methylidene]-
7.57-7.63 (m, 5H, ArH), 8.42 (d, 2H, J 8.1 Hz, ArH);
C NMR (126 MHz, DMSO-d ) d 40.6, 110.4, 111.9,
6
1
3
-isoxazolone(3d, C H NO )
12
11
2
-1
Yellow crystal; mp 132-133 ºC; IR (KBr) ν/cm 1753,
122.2, 129.1, 129.3, 129.4, 130.7, 138.4, 152.1, 154.9,
1
+
1636; H NMR (500 MHz, DMSO-d ) d 2.32 (s, 3H, CH );
165.2, 170.8; MS m/z 292 (100%, M ), 234 (5%), 144
6
3
2
.49 (s, 3H, CH ); 7.35 (d, 2H, J 8.1 Hz, ArH); 7.43 (s, 1H,
(18%), 117 (30%).
3
13
vinyl); 8.32 (d, 2H, J 8.2 Hz, ArH); C NMR (126 MHz,
DMSO-d ) d 12.0, 22.5, 118.9, 130.3, 130.4, 134.6, 146.1,
4-[1-(4-Methoxyphenyl)methylidene]-3-phenyl-
6
+
150.3, 161.6, 168.6; MS m/z 201(100%, M ), 186 (67%), 145
5-isoxazolone (3i, C H NO )
17
13
3
-1
(
50%), 128 (81%); CHN (C H NO ) calc. (%) C (71.66),
Yellow crystal; mp 166-167 ºC; IR (KBr) ν/cm 1753,
12
11
2
1
H (5.47), N (6.96); found (%) C (71.78), H (5.46), N (6.81).
1612; H NMR (500 MHz, DMSO-d ) d 3.96 (s, 3H, OCH );
6
3
7
.04 (d, 2H, J 8.9 Hz, ArH); 7.56 (s, 1H, vinyl); 7.70-7.64
1
3
3
-Methyl-4-[1-(2-thienyl) methylidene]-5-isoxazolone (3e,
(m, 5H, ArH), 8.45 (d, 2H, J 8.9 Hz, ArH); C NMR
C H NO S)
(126 MHz, DMSO-d ) d 56.2, 115.1, 115.8, 126.4, 128.2,
9
7
2
6
-1
Yellow brown crystal; mp 148-149 ºC; IR (KBr) ν/cm
129.2, 129.6, 131.2, 137.7, 152.5, 164.8 165.3, 169.4; MS
1
+
1
753, 1612; H NMR (500 MHz, DMSO-d ) d 2.32 (s, 3H,
m/z 279 (100%, M ), 221 (14%), 132 (16%).
6