M. Ghazanfarpour-Darjani, A. Khodakarami
136 °C; IR (KBr): vꢀ = 3046, 2981, 1623, 1548, 1338,
d = 0.5 (3 Me), 10.8 (CH2), 24.1 (Me), 29.3 (CH2), 36.6
(CH2), 62.3 (CH), 120.3 (2 CH), 126.7 (CH), 128.0 (2 CH),
130.6 (2 CH), 131.4 (2 CH), 135.2 (C), 141.4 (C), 149.48
(C), 165.8 (C) ppm; EI-MS (70 eV): m/z (%) = 432 (M?,
2), 277 (21), 170 (45), 155 (78), 77 (100).
1
1305, 1109 cm-1; H NMR (500 MHz, CDCl3): d = 2.32
(s, Me), 4.62 (s, CH), 5.38 (s, CH), 7.08-7.31 (m, 15 CH),
3
3
7.35 (d, J = 6.7 Hz, 2 CH), 7.83 (d, J = 6.9 Hz, 2 CH)
ppm; 13C NMR (125.7 MHz, CDCl3): d = 24.0 (Me), 45.1
(CH), 69.6 (CH), 121.2 (2 CH), 126.0 (CH), 127.1 (2 CH),
128.0 (2 CH), 128.2 (CH), 128.5 (CH), 128.7 (2 CH), 129.0
(2 CH), 129.5 (2 CH), 130.3 (2 CH), 132.5 (2 CH), 135.2
(C), 140.8 (C), 142.1 (C), 143.1 (C), 149.4 (C), 164.2
(C) ppm; EI-MS (70 eV): m/z (%) = 484 (M?, 2), 330
(42), 329 (11), 170 (72), 155 (52), 77 (100).
N-[4-[(Benzyloxy)methyl]-3-tosylthiazolidin-2-ylidene]-
benzenamine (8h, C24H24N2O3S2)
The crude product was purified by cold etheric extraction
affording 0.39 g (87 %) 8h. Pale yellow solid; m.p.: 132–
134 °C; IR (KBr): vꢀ = 3052, 2972, 1652, 1551, 1344,
1
1310, 1109 cm-1; H NMR (500 MHz, CDCl3): d = 2.34
N-(4-Benzyl-3-tosylthiazolidin-2-ylidene)benzenamine
(8c, C23H22N2O2S2)
(s, Me), 3.32–3.48 (m, CH2), 4.51–4.79 (m, 2 CH2),
5.26–5.29 (m, CH), 7.11–7.29 (m, 10 CH), 7.31 (d,
3
The crude product was purified by cold etheric extraction
affording 0.38 g (89 %) 8c. Pale yellow solid; m.p.: 100-
102 °C; IR (KBr): vꢀ = 3046, 2978, 1644, 1542, 1346,
3J = 6.7 Hz, 2 CH), 7.82 (d, J = 6.3 Hz, 2 CH) ppm;
13C NMR (125.7 MHz, CDCl3): d = 24.2 (Me), 34.5
(CH2), 69.9 (CH), 71.2 (CH2), 81.1 (CH2), 121.3 (2 CH),
127.1 (CH), 127.5 (2 CH), 128.1 (CH), 129.1 (2 CH), 129.6
(2 CH), 130.1 (2 CH), 131.4 (2 CH), 135.0 (C), 137.4 (C),
143.4 (C), 149.9 (C), 165.7 (C) ppm; EI-MS (70 eV):
m/z (%) = 452 (M?, 2), 297 (18), 170 (70), 155 (51), 91
(100), 77 (62).
1
1312, 1110 cm-1; H NMR (500 MHz, CDCl3): d = 2.34
(s, Me), 2.79–2.85 (m, 2 CH), 3.41–3.47 (m, 2 CH),
5.13–5.16 (m, CH), 7.08–7.29 (m, 10 CH), 7.31 (d,
3
3J = 6.8 Hz, 2 CH), 7.83 (d, J = 6.4 Hz, 2 CH) ppm;
13C NMR (125.7 MHz, CDCl3): d = 24.3 (Me), 35.9
(CH2), 43.7 (CH2), 67.9 (CH), 121.8 (2 CH), 125.3 (CH),
126.7 (2 CH), 127.1 (CH), 127.6 (2 CH), 128.0 (2 CH),
129.8 (2 CH), 131.4 (2 CH), 135.0 (C), 136.3 (C), 142.3
(C), 149.0 (C), 164.7 (C) ppm; EI-MS (70 eV):
m/z (%) = 422 (M?, 5), 267 (18), 155 (69), 91 (100), 77 (58).
N-(4-Benzyl-3-tosylthiazolidin-2-ylidene)-4-methylbenzen-
amine (8k, C24H24N2O2S2)
The crude product was purified by cold etheric extraction
affording 0.39 g (89 %) 8k. Pale yellow solid; m.p.: 101–
103 °C; IR (KBr): vꢀ = 3046, 2977, 1652, 1550, 1343,
1
N-(3-Tosylthiazolidin-2-ylidene)benzenamine
(8f, C16H16N2O2S2)
1310, 1107 cm-1; H NMR (500 MHz, CDCl3): d = 2.29
(s, Me), 2.32 (s, Me), 2.73–2.80 (m, 2 CH), 3.35–3.43 (m, 2
CH), 5.15–5.19 (m, CH), 7.10 (d, 3J = 6.7 Hz, 2 CH),
7.15–7.28 (m, 7 CH), 7.33 (d, 3J = 6.5 Hz, 2 CH), 7.85 (d,
3J = 6.9 Hz, 2 CH) ppm; 13C NMR (125.7 MHz, CDCl3):
d = 23.2 (Me), 24.5 (Me), 36.5 (CH2), 40.3 (CH2), 68.1
(CH), 123.1 (2 CH), 126.0 (CH), 127.1 (2 CH), 127.5 (2
CH), 128.0 (2 CH), 130.6 (2 CH), 132.1 (2 CH), 135.1 (C),
135.7 (C), 139.2 (C), 141.6 (C), 148.3 (C), 165.2 (C) ppm;
EI-MS (70 eV): m/z (%) = 436 (M?, 2), 128 (23), 170
(38), 155 (45), 91 (100), 77 (63).
The crude product was purified by cold etheric extraction
affording 0.31 g (94 %) 8f. Pale yellow solid; m.p.: 86–
88 °C; IR (KBr): vꢀ = 3037, 2977, 1652, 1549, 1342, 1311,
1110 cm-1 1H NMR (500 MHz, CDCl3): d = 2.24 (s,
;
Me), 3.49 (t, 3J = 6.7 Hz, CH2), 4.72 (t, 3J = 6.5 Hz,
3
CH2), 7.10 (d, J = 6.9 Hz, 2 CH), 7.18–7.29 (m, 3 CH),
3
3
7.32 (d, J = 6.5 Hz, 2 CH), 7.81 (d, J = 6.9 Hz, 2 CH)
ppm; 13C NMR (125.7 MHz, CDCl3): d = 24.1 (Me), 34.9
(CH2), 59.8 (CH2), 121.1 (2 CH), 126.0 (CH), 128.2 (2
CH), 130.2 (2 CH), 131.7 (2 CH), 135.8 (C), 142.2 (C),
149.5 (C), 164.9 (C) ppm; EI-MS (70 eV): m/z (%) = 207
(M?, 2), 170 (61), 155 (48), 91 (39), 77 (100).
N-(4-Benzyl-3-tosylthiazolidin-2-ylidene)propan-2-amine
(8l, C20H24N2O2S2)
The crude product was purified by cold etheric extraction
affording 0.29 g (75 %) 8l. Pale yellow solid; m.p.: 67–
69 °C; IR (KBr): vꢀ = 3046, 2977, 1652, 1544, 1349, 1311,
N-[4-[2-(Trimethylsilyl)ethyl]-3-tosylthiazolidin-2-ylidene]-
benzenamine (8g, C21H28N2O2S2Si)
The crude product was purified by cold etheric extraction
affording 0.38 g (89 %) 8g. Pale yellow solid; m.p.: 116–
118 °C; IR (KBr): vꢀ = 3048, 2970, 1648, 1544, 1343,
1108 cm-1 1H NMR (500 MHz, CDCl3): d = 1.15 (d,
;
3J = 7.0 Hz, 2 Me), 2.32 (s, Me), 2.78–2.89 (m, 2 CH),
3.20–3.41 (m, 3 CH), 5.11–5.14 (m, CH), 7.07 (d,
3
1
1311, 1116 cm-1; H NMR (500 MHz, CDCl3): d = 0.08
3J = 6.4 Hz, 2 CH), 7.19 (t, J = 7.1 Hz, CH), 7.25 (d,
(s, 3 Me), 0.79 (t, 3J = 7.1 Hz, CH2), 1.70–1.74 (m, CH2),
2.32 (s, Me), 3.39–3.45 (m, CH2), 5.08–5.12 (m, CH), 7.13
(d, 3J = 6.9 Hz, CH), 7.18 (t, 3J = 7.0 Hz, 2 CH), 7.25 (d,
3J = 6.7 Hz, 2 CH), 7.31 (d, J = 6.5 Hz, 2 CH), 7.82 (d,
3
3J = 6.7 Hz, 2 CH) ppm; 13C NMR (125.7 MHz, CDCl3):
d = 21.1 (2 Me), 24.2 (Me), 37.1 (CH2), 41.5 (CH2), 49.2
(CH), 67.3 (CH), 125.2 (CH), 126.7 (2 CH), 127.3 (2 CH),
128.1 (2 CH), 130.3 (2 CH), 135.8 (C), 137.5 (C), 142.1
3
3J = 6.4 Hz, 2 CH), 7.34 (d, J = 6.8 Hz, 2 CH), 7.83 (d,
3J = 6.5 Hz, 2 CH) ppm; 13C NMR (125.7 MHz, CDCl3):
123