Jul-Aug 2006
Microwave Induced Synthesis of the Thiazolidine-2,4-dione Motif
901
7
.69 (m, 2H, ArH), 7.68 (s, 1H, =CHAr), 13.90(bs, 1H, NH).
13.7 (bs, 1H, NH); MS: m/z (%) found 235.8 (100), calcd 236
(M-H) . 176.6, 131.0.
-
-
MS: m/z (%) found 238.0 (100), calcd 238 (M-H) . 189.2, 131.0,
06.0.
Anal. Calcd. for C H FNOS : C, 50.19; H, 2.53; N, 5.85.
1
Anal. Calcd. for C H NO S : C, 50.62; H, 2.97; N, 5.90.
1
0
7
2 2
Found: C, 50.45; H, 2.69; N, 5.72.
10
6
2
Found: C, 49.88; H, 2.61; N, 5.73.
(Z)-5-(4-Benzyloxy-3-methoxybenzylidene)-thiazolidine-2,4-
(Z)-5-(4-Chlorobenzylidene)-thiazolidine-2,4-dione (4).
dione (10).
This compound was obtained according to the above general
This compound was obtained according to the above general
procedure for Knoevenagel condensation reaction as a pale
yellow solid; mp 221-223 °C; H NMR: ꢀ (ppm) 3.84 (s, 3H,
procedure for Knoevenagel condensation reaction as a white
1
1
crystals; mp 255-257 °C; H NMR: ꢀ (ppm) 7.39 (m, 2H, ArH),
7
.67 (m, 2H, ArH), 7.88 (s, 1H, =CHAr), 12.58 (bs, 1H, NH);
OCH ), 5.15 (s, 2H, OCH ), 7.14-7.23 (m, 3H, ArH), 7.36 (m,
3
2
-
MS: m/z (%) found 238.0 (100), calcd 238 (M-H) . (M-H)+2
5H, ArH), 7.75 (s, 1H, =CHAr), 12.51 (bs, 1H, NH); MS: m/z
3
7
34
18
-
(37.21%, 1 Cl + 1 S + 2 O), 201.0, 167.0, 116.2.
(%) found 340.0 (100), calcd 340 (M-H) .325.1, 289.0, 248.8,
Anal. Calcd. for C H ClNO S: C, 50.11; H, 2.52; N, 5.84.
116.2, 91.0, 76.5.
10
6
2
Found: C, 50.11; H, 2.59; N, 5.69.
Anal. Calcd. for C H NO S: C, 63.33; H, 4.43; N, 4.10.
1
8
15
4
Found: C, 63.48; H, 4.40; N, 4.23.
(Z)-5-(4-Chlorobenzylidene)-2-thioxo-thiazolidine-4-one (5).
(
Z)-5-(4-Benzyloxy-3-methoxybenzylidene)-2-thioxo-
This compound was obtained according to the above general
thiazolidine-4-one (11).
procedure for Knoevenagel condensation reaction as a pale
1
yellow solid; mp 227-230 °C; H NMR: ꢀ (ppm) 7.41(m, 2H,
This compound was obtained according to the above general
ArH), 7.65 (m, 2H, ArH), 7.86 (s, 1H, =CHAr), 13.74 (bs, 1H,
procedure for Knoevenagel condensation reaction as a pink
-
1
NH); MS: m/z (%) found 253.8 (100), calcd 254 (M-H) . (M-
solid; mp 216-219 °C; H NMR: ꢀ (ppm) 3.84 (s, 3H, OCH ),
3
3
7
34
18
H)+2 (41.38%, 1 Cl + 2 S + 1 O), 119.2, 131.0.
5.15 (s, 2H, OCH ), 7.16-7.24 (m, 3H, ArH), 7.36 (m, 5H, ArH),
2
Anal. Calcd. for C H ClNOS : C, 46.97; H, 2.36; N, 5.48.
Found: C, 47.12; H, 2.53; N, 5.31.
7.71 (s, 1H, =CHAr), 13.86 (bs, 1H, NH); MS: m/z (%) found
356.01 (100), calcd 356 (M-H) . 272.0, 162.1, 91.0, 76.5.
10
6
2
-
Anal. Calcd. for C H NO S : C, 60.48; H, 4.23; N, 3.92.
Found: C, 60.58; H, 4.15; N, 3.79.
1
8
15
3 2
(Z)-5-(4-Methoxybenzylidene)-thiazolidine-2,4-dione (6).
This compound was obtained according to the above general
(
Z)-5-(3-Hydroxybenzylidene)-thiazolidine-2,4-dione (12).
procedure for Knoevenagel condensation reaction as a yellow
1
solid; mp 217-219 °C; H NMR: ꢀ (ppm) 3.81(s, 3H, OCH ),
This compound was obtained according to the above general
3
7
1
.09 (m, 2H, ArH), 7.56 (m, 2H, ArH), 7.75 (s, 1H, =CHAr),
procedure for Knoevenagel condensation reaction as a cream
solid; mp 291-294 °C; H NMR: ꢀ (ppm) 6.8-7.1 (m, 3H, ArH),
1
2.49 (bs, 1H, NH); MS: m/z (%) found 234.0 (100), calcd 234
-
(M-H) . 163.0, 120.0, 116.2.
7.3 (m, 1H, ArH), 7.72 (s, 1H, =CHAr), 9.96 (s, 1H, ArOH),
-
Anal. Calcd. for C H NO S: C, 56.16; H, 3.86; N, 5.95.
12.62 (bs, 1H, NH); MS: m/z (%) found 220.0, calcd 220 (M-H)
11
9
3
Found: C, 55.91; H, 4.06; N, 5.89.
.149.2 (100), 116.2
Anal. Calcd. for C H NO S: C, 54.29; H, 3.19; N, 6.33.
Found: C, 54.10; H, 3.30; N, 6.29.
1
0
7
3
(Z)-5-(4-Methoxybenzylidene)-2-thioxo-thiazolidine-4-one (7).
This compound was obtained according to the above general
(
Z)-5-(3-Hydroxybenzylidene)-2-thioxo-thiazolidine-4-one (13).
procedure for Knoevenagel condensation reaction as yellow
1
crystals; mp 233-235 °C; H NMR: ꢀ (ppm) 3.82 (s, 3H, OCH ),
This compound was obtained according to the above general
3
7
1
.10 (m, 2H, ArH), 7.56 (m, 2H, ArH), 7.62 (s, 1H, =CHAr),
procedure for Knoevenagel condensation reaction as a yellow
solid; mp 258-261°C; H NMR: ꢀ (ppm) 6.94 (m, 3H, ArH),
1
3.72 (bs, 1H, NH); MS: m/z (%) found 250.0 (100), calcd 250
-
(M-H) . 105.0, 131.0, 92.0.
7.34 (m, 1H, ArH), 7.73 (s, 1H, =CHAr), 9.98 (s, 1H, ArOH),
13.82 (bs, 1H, NH); MS: m/z (%) found 237.8, calcd 238
Anal. Calcd. for C H NO S : C, 52.57; H, 3.61; N, 5.57.
11
9
2 2
+
Found: C, 52.59; H, 3.74; N, 5.35.
(M+H) . 205.0, 149.2, 131.0 (100).
Anal. Calcd. for C H NO S : C, 50.62; H, 2.97; N, 5.90.
Found: C, 50.51; H, 2.75; N, 5.89.
1
0
7
2 2
(Z)-5-(4-Hydroxybenzylidene)-thiazolidine-2,4-dione (8).
This compound was obtained according to the above general
(
Z)-5-Benzylidene-thiazolidine-2,4-dione (14).
procedure for Knoevenagel condensation reaction as a yellow
1
solid; mp >300 °C; H NMR: ꢀ (ppm) 6.92 (m, 2H, ArH), 7.40 (m,
This compound was obtained according to the above general
2
1
1
H, ArH), 7.68 (s, 1H, =CHAr), 10.28 (s, 1H, ArOH), 12.42 (bs,
H, NH); MS: m/z (%) found 220.2 (100), calcd 220 (M-H) .
48.2, 120.1.
procedure for Knoevenagel condensation reaction as a pale
yellow crystals; mp 248-250 °C; H NMR: ꢀ (ppm) 7.47 - 7.59
-
1
(m, 5H, ArH), 7.79(s, 1H, =CHAr), 12.62 (bs, 1H, NH); MS:
-
Anal. Calcd. for C H NO S: C, 54.29; H, 3.19; N, 6.33.
m/z (%) found 204.0 (100), calcd 204 (M-H) . 132.4, 116.2,
10
7
3
Found: C, 54.10; H, 3.30; N, 6.29.
41.4.
Anal. Calcd. for C H NO S: C, 58.52; H, 3.44; N, 6.82.
Found: C, 58.69; H, 3.51; N, 6.77.
1
0
7
2
(Z)-5-(4-Hydroxybenzylidene)-2-thioxo-thiazolidine-4-one (9).
This compound was obtained according to the above general
(
Z)-5-Benzylidene-2-thioxo-thiazolidine-4-one (15).
procedure for Knoevenagel condensation reaction as a pink
1
solid; mp 287-290 °C; H NMR: ꢀ (ppm) 6.92 (m, 2H, ArH),
This compound was obtained according to the above general
7
.42 (m, 2H, ArH), 7.58 (s, 1H, =CHAr), 10.44 (s, 1H, ArOH),
procedure for Knoevenagel condensation reaction as a yellow