300
X. Xu et al. / Journal of Fluorine Chemistry 126 (2005) 297–300
0
3.3.6. Syntheses of 2-(4-fluorophenylimino)-tetrahydro-
thiazolidine (3f)
0.36H, H-20 and H-60), 7.10 (q, 1H, J4 5 = 8.9 Hz,
J6 5 = 8.9 Hz, J3 5 = 8.3 Hz, H-5 ). IR (KBr) (cmꢀ1):
3150 (NH), 2950, 2875, 1620 (C=N), 1600, 1500, 1300,
1260, 1230 (C–S), 1000, 820. MS (EI, 70 eV): m/z (%): 260
(79.16) [M], 245 (100.00) [M ꢀ CH3], 213 (6.70)
[M ꢀ SCH3], 172 (28.62), 147 (12.96), 88 (29.87), 55
(29.98). HRMS Calcd. for C11H11F3N2S 260.0595. Found:
260.0612.
0
0
0
0 0
Yield 84%, mp 153–154 8C. 1H NMR (CD3COCD3,
500 MHz) d: 3.32 (t, 2H, J = 7.2 Hz, H-5), 3.92 (s, 2H, H-4),
7.01 (m, 2H, H-30 and H-50), 7.40 (br S, 2H, H-20 and H-60).
IR (KBr) (cmꢀ1): 3125 (NH), 2800, 1630 (C=N), 1600, 1500
(Ph), 1300, 1200, 1180, 780, 620. MS (EI, 70 eV): m/z (%):
196 (93.04) [M], 168 (11.72) [M ꢀ CH2=CH2], 149 (12.52)
[M ꢀ SCH3], 136 (100.00) [M ꢀ C2H4S], 122 (32.36)
[M ꢀ C2H4NS], 109 (22.65) [M ꢀ C3H5NS], 95 (17.34).
HRMS Calcd. for C9H9 FN2S 196.0470. Found: 196.0479.
Acknowledgement
3.3.7. Syntheses of 2-(2,3,4-trifluorophenylimino)-
tetrahydro-thiazolidine (3g)
This work was partly supported by Shanghai Education
Committee, National Natural Science Foundation of China,
and Minister of Science and Technology (2001AA235011;
2003CB114405).
Yield 80%, mp 151–152 8C. 1H NMR (CD3COCD3,
500 MHz) d: 3.39 (t, 2H, J = 7.0 Hz, H-5), 3.74 (t, 2H,
J = 7.0 Hz, H-4), 6.90 (br S, 1H, H-60), 7.06 (q, 1H,
0
0
0
0
0 0
J
4 5 = 10.4 Hz, J6 5 = 10.4 Hz, J3 5 = 9.2 Hz, H-5 ). IR
(KBr) (cmꢀ1): 3150 (NH), 2850, 1650 (C=N), 1630,
1600, 1500, 1450 (Ph), 1320, 1230, 1040, 980. MS (EI,
70 eV): m/z (%): 232 (100.00) [M], 213 (77.11) [M ꢀ F],
185 (13.55) [M ꢀ SCH3], 172 (88.86) [M ꢀ SC2H4], 158
(25.37): [M ꢀ C2H4NS], 145 (12.94), 61 (9.61). HRMS
Calcd. for C9H7F3N2S 232.0282. Found: 232.0296.
References
[1] O. Ando, H. Satake, K. Itoil, A. Sato, M. Nakajima, H. Haruyama, Y.
Ohkuma, T. Kinoshita, R. Enokita, J. Antibiot. 44 (1991) 1165–1168.
[2] O. Ando, M. Nakajima, M. Kifune, H. Fang, K. Tanzawa, Biochim.
Biophys. Acta 1244 (1995) 295–302.
[3] Y. Kobayashi, Carbohydr. Res. 315 (1999) 3–15.
[4] Y. Kobayashi, H. Miyazaki, M. Shiozaki, J. Antibiot. 47 (1994) 932–
938.
3.3.8. Syntheses of 2-(2,3,4-trifluorophenylimino)-4-ethyl-
4-hydroxymethyl-thiazolidine (3h)
[5] T. Nakayama, T. Amachi, S. Murao, T. Sakai, T. Shin, P.T. Kenny, T.
Iwashita, M. Zagorski, H. Komura, K. Nomoto, J. Chem. Soc., Chem.
Commun. (1991) 919–920.
Yield 52%, mp 165–166 8C. 1H NMR (CD3COCD3,
500 MHz) d: 1.00 (t, 3H, J = 7.5 Hz, CH3), 1.78 (q, 2H,
J = 7.5 Hz, CH2), 3.31 (d, 1H, J = 11.1 Hz, Ha(b)-5), 3.53 (d,
1H, J = 11.1 Hz, Hb(a)-5), 3.56 (d, 1H, J = 11.1 Hz,
CH2a(2b)OH), 3.71 (d, 1H, J = 11.1 Hz, CH2b(2a)OH), 6.87
[6] T. Iwase, E. Higashide, H. Yamamoto, M. Shitata, J. Antibiot. 24
(1971) 107–113.
[7] O. Ando, M. Klfune, M. Nakajima, Biosci. Biotechnol. Biochem. 59
(1995) 711–712.
(br S, 0.6H, H-60), 7.05 (q, 1H, J2 5 = 9.1 Hz, J4 5 = 10.1 Hz,
0
0
0 0
[8] B.M. Trost, D.L. Van Vrankon, J. Am. Chem. Soc. 115 (1993) 444–
458.
J3 5 = 8.4 Hz, H-5 ). IR (KBr) (cmꢀ1): 3300 (OH), 3100,
2875, 1630 (C–N), 1500 (Ph), 1250 (C–S), 1220, 1050, 980,
820. MS (EI, 70 eV) m/z (%): 290 (7.33) [M], 259 (100.00)
[M ꢀ CH2OH], 231 (36.64): [M ꢀ C3H7O], 172 (6.08), 102
(24.29), 87 (9.46). HRMS Calcd. for C12H13F3N2OS
290.0701. Found: 290.0702.
0
0
0
[9] J. Li, F. Lang, B. Ganem, J. Org. Chem. 63 (1998) 3403–3410.
[10] S. Ogawa, C. Uchida, Chem. Lett. (1993) 173–176.
[11] C. Uchida, T. Yamagishi, S. Ogawa, J. Chem. Soc., Prekin Trans. I
(1994) 589–602.
[12] K. Yoshiyuki, M. Hideki, S. Masao, J. Org. Chem. 59 (1994)
813–822.
[13] M. Hudlicky, Chemistry of Organic Fluorine Compounds II, American
Chemical Society, Washington, DC, 1995, p. 979, 1145.
[14] Z. Li, X. Qian, G. Song, Z. Li, J. Fluorine Chem. 108 (2001) 143–146.
[15] Z. Li, X. Qian, Org. Prep. Proc. Int. 32 (2000) 571–573.
[16] K. Hostettmann, J.B. Harborne, P.M. Dey, Methods in Plant Biochem-
istry, vol. 6, Academic Press, London, UK, 1991, pp. 33–46.
3.3.9. Syntheses of 2-(2,3,4-trifluorophenylimino)-4,4-
dimethyl-thiazolidine (3i)
Yield 73%, mp 195–196 8C. 1H NMR (CD3COCD3,
500 MHz) d: 1.43 (s, 6H, CH3), 3.22 (s, 2H, H-5), 6.81 (br S,