M. Khalaj et al.
2 ‑ B e n z y l i d e n e ‑ 5 ‑ p h e n y l ‑ 3 ‑ t o s y l t h i a z o l i d i n e
(4g,C23H21NO2S2) Pale yellow solid; m.p.: 105–107 °C;
yield: 0.37 g (90%); IR (KBr): v̄ =3021, 2978, 1565, 1344,
1310, 1136 cm−1; 1H NMR (500.1 MHz, CDCl3): δ=2.48
CH), 3.19 (1H, dd, 2J=10.5 Hz, 3J=5.3 Hz, CH), 3.31 (1H,
dd, 2J=10.5 Hz, 3J=8.7 Hz, CH), 3.55–3.63 (1H, m, CH),
4.53 (1H, t, 3J=6.1 Hz, CH), 7.17–7.33 (5H, m, 5 CH), 7.39
(2H, d, 3J=6.4 Hz, 2 CH), 7.68 (2H, d, 3J=6.4 Hz, 2 CH)
ppm; 13C NMR (125.7 MHz, CDCl3): δ=15.6 (Me), 24.1
(CH2), 24.5 (Me), 30.3 (CH2), 40.4 (CH2), 43.1 (CH2), 62.5
(CH), 96.3 (CH), 125.4 (CH), 127.6 (2 CH), 129.2 (2 CH),
129.6 (2 CH), 131.6 (2 CH), 134.9 (C), 138.3 (C), 138.9 (C),
159.7 (C) ppm; MS: m/z (%)=387 (M+, 4), 296 (24), 155
(50), 141 (49), 91 (100), 77 (80).
3
(3H, s, Me), 3.95–4.05 (1H, dd, J=11.7 Hz, 3J=7.1 Hz,
2
3
CH), 4.38 (1H, dd, J = 12.4 Hz, J = 5.6 Hz, CH), 4.71
(1H, dd, 2J=12.4 Hz, 3J=9.8 Hz, CH), 5.35 (1H, s, CH),
7.18–7.46 (10H, m, 10 CH), 7.59 (2H, d, 3J=6.7 Hz, 2 CH),
7.71 (2H, d, 3J=6.5 Hz, 2 CH) ppm; 13C NMR (125.7 MHz,
CDCl3): δ = 24.2 (Me), 54.6 (CH), 66.9 (CH), 97.2 (CH),
126.1 (CH), 126.4 (CH), 127.0 (2 CH), 128.3 (2 CH), 128.5
(2 CH), 129.1 (2 CH), 129.5 (2 CH), 130.6 (2 CH), 134.4
(C), 135.9 (C), 138.8 (C), 139.7 (C), 153.6 (C) ppm; MS:
m/z (%) = 407 (M+, 7), 296 (22), 294 (57), 155 (44), 77
(100), 54 (48).
4‑Benzyl‑2‑(furan‑2‑ylmethylene)‑3‑tosylthiazolidine
(4k,C22H21NO3S2) Pale yellow solid; m.p.: 94–96 °C; yield:
0.38 g (92%); IR (KBr): v̄ =3030, 2982, 1664, 1563, 1372,
13,218, 1144 cm−1; 1H NMR (500.1 MHz, CDCl3): δ=2.45
2
3
(3H, s, Me), 2.78 (1H, dd, J=11.2 Hz, J=5.4 Hz, CH),
2.93 (1H, dd, 2J=11.2 Hz, 3J=9.7 Hz, CH), 3.15 (1H, dd,
2J=12.4 Hz, 3J=4.9 Hz, CH), 3.33 (1H, dd, 2J=12.4 Hz,
3J=8.9 Hz, CH), 3.72–3.79 (1H, m, CH), 5.35 (1H, s, CH),
6.67 (1H, t, 3J=6.3 Hz, CH), 6.97 (1H, d, 3J=6.7 Hz, CH),
7.16–7.33 (5H, m, 5 CH), 7.40 (2H, d, 3J=6.5 Hz, 2 CH),
2‑Benzylidene‑4‑methyl‑5‑phenyl‑3‑tosylthiazolidine
(4h,C24H23NO2S2) Yellow powder; m.p.: 143–145 °C; yield:
0.36 g (85%); IR (KBr): v̄ =3026, 2981, 1562, 1361, 1321,
1132 cm−1; 1H NMR (500.1 MHz, CDCl3): δ=1.38 (3H, d,
3J=5.8 Hz, Me), 2.45 (3H, s, Me), 3.60 (1H, d, 3J=6.2 Hz,
CH), 3.87 (1H, d, 3J=6.2 Hz, CH), 5.33 (1H, s, CH), 7.17–
7.46 (10H, m, 10 CH), 7.58 (2H, d, 3J=6.5 Hz, 2 CH), 7.69
3
3
7.69 (2H, d, J = 6.5 Hz, 2 CH), 7.80 (1H, d, J = 6.3 Hz,
CH) ppm; 13C NMR (125.7 MHz, CDCl3): δ= 24.3 (Me),
39.1 (CH2), 45.2 (CH2), 67.3 (CH), 95.1 (CH), 111.5 (CH),
112.2 (CH), 125.8 (CH), 127.6 (2 CH), 128.1 (2 CH), 129.2
(2 CH), 129.5 (2 CH), 134.1 (C), 137.6 (C), 137.9 (C), 145.7
(CH), 153.6 (C), 164.9 (C) ppm; MS: m/z (%)=411 (M+, 5),
300 (19), 221 (35), 155 (52), 91 (100), 67 (51).
3
(2H, d, J = 6.7 Hz, 2 CH) ppm; 13C NMR (125.7 MHz,
CDCl3): δ = 15.6 (Me), 24.3 (Me), 58.4 (CH), 68.4 (CH),
96.5 (CH), 125.3 (CH), 126.1 (CH), 127.2 (2 CH), 127.5 (2
CH), 128.1 (2 CH), 128.9 (2 CH), 129.7 (2 CH), 131.4 (2
CH), 134.2 (C), 134.9 (C), 138.7 (C), 141.3 (C), 151.2 (C)
ppm; MS: m/z (%) = 421 (M+, 1), 406 (12), 251 (29), 190
(40), 155 (57), 77 (100).
4‑Benzyl‑3‑tosyl‑2‑[(trimethylsilyl)methylene]thiazolidine
(4l,C21H27NO2S2Si) Pale yellow solid; m.p.: 78–80 °C; yield:
0.28 g (68%); IR (KBr): v̄ =3041, 2971, 1641, 1547, 1326,
1309, 1107 cm−1; 1H NMR (500.1 MHz, CDCl3): δ=0.01
(9H, s, 3 Me), 2.44 (3H, s, Me), 2.75 (1H, dd, 2J=11.8 Hz,
2‑Benzylidene‑5‑methyl‑5‑phenyl‑3‑tosylthiazolidine
(4i,C24H23NO2S2) Yellow powder; m.p.: 102–104 °C; yield:
0.29 g (70%); IR (KBr): v̄ =3026, 2982, 1563, 1365, 1334,
1148 cm−1; H NMR (500.1 MHz, CDCl3): δ = 1.78 (3H,
3J = 7.1 Hz, CH), 2.93 (1H, dd, J = 11.8 Hz, J = 4.5 Hz,
CH), 3.15 (1H, dd, 2J=10.8 Hz, 3J=8.5 Hz, CH), 3.34 (1H,
dd, 2J=10.8 Hz, 3J=4.9 Hz, CH), 3.76–3.84 (1H, m, CH),
4.78 (1H, s, CH), 7.17–7.30 (5H, m, 5 CH), 7.37 (2H, d,
1
2
3
2
s, Me), 2.45 (3H, s, Me), 4.33 (1H, d, J = 10.6 Hz, CH),
4.65 (1H, d, 2J=10.6 Hz, CH), 5.25 (1H, s, CH), 7.18–7.47
(10H, m, 10 CH), 7.61 (2H, d, 3J=6.4 Hz, 2 CH), 7.69 (2H,
d, 3J=6.5 Hz, 2 CH) ppm; 13C NMR (125.7 MHz, CDCl3):
δ=24.2 (Me), 27.3 (Me), 57.3 (C), 68.4 (CH2), 97.6 (CH),
125.3 (CH), 126.0 (2 CH), 126.3 (CH), 127.7 (2 CH), 128.6
(2 CH), 128.8 (2 CH), 129.3 (2 CH), 130.4 (2 CH), 134.3
(C), 135.7 (C), 139.4 (C), 151.0 (C), 154.8 (C) ppm; MS:
m/z (%) = 421 (M+, 6), 406 (15), 344 (31), 266 (42), 155
(64), 77 (100).
3J=6.7 Hz, 2 CH), 7.69 (2H, d, 3J=6.7 Hz, 2 CH) ppm; 13
C
NMR (125.7 MHz, CDCl3): δ=1.1 (3 Me), 23.9 (Me), 37.1
(CH2), 41.8 (CH2), 69.9 (CH), 84.7 (CH), 126.4 (CH), 128.0
(2 CH), 128.6 (2 CH), 129.5 (2 CH), 129.8 (2 CH), 134.9
(C), 138.6 (C), 139.5 (C), 178.3 (C) ppm; MS: m/z (%)=417
(M+, 4), 306 (22), 221 (34), 155 (46), 91 (100), 77 (68).
4 ‑ B e n z y l ‑ 2 ‑ b u t y l i d e n e ‑ 3 ‑ t o s y l t h i a z o l i d i n e
(4j,C21H25NO2S2) Yellow powder; m.p.: 84–86 °C; yield:
0.29 g (76%); IR (KBr): v̄ =3025, 2961, 1567, 1371, 1319,
References
1
1145 cm−1; H NMR (500.1 MHz, CDCl3): δ = 0.88 (3H,
1. Li H, Liu J, Yan B, Li Y (2009) Tetrahedron Lett 50:2353
2. Yoo WJ, Lia CJ (2008) Adv Synth Catal 350:1503
3. Patil NT, Raut VS (2010) J Org Chem 75:6961
3
t, J = 6.1 Hz, Me), 1.42–1.53 (2H, m, CH2), 2.26–2.37
(2H, m, CH2), 2.40 (3H, s, Me), 2.85 (1H, dd, 2J=10.7 Hz,
2
3
3J = 5.5 Hz, CH), 3.02 (1H, dd, J = 10.7 Hz, J = 8.9 Hz,
4. Pappo R, Collins PW (1972) Tetrahedron Lett 13:2627
1 3