7976
N. Chen et al. / Tetrahedron 67 (2011) 7971e7976
(s, 1H), 3.64 (d, J¼11.2 Hz, 1H), 3.62 (d, J¼11.2 Hz, 1H), 1.87 (s, 3H).
13C NMR (100 MHz, CDCl3)
: 200.1, 142.4, 129.0, 128.3, 124.7, 72.1,
(s, 1H), 4.23 (d, J¼11.2 Hz, 1H), 3.93 (d, J¼11.2 Hz, 1H), 1.99 (s, 3H).
13C NMR (100 MHz, CDCl3)
: 200.8, 141.6, 128.9, 128.1, 126.0, 63.6,
d
d
47.6, 26.5. IR (CDCl3)
n
(cmꢂ1): 3131 (NH), 1494 (NeC]S). HRMS
62.9, 29.1. IR (CDCl3) n
(cmꢂ1): 3151 (NH), 1491 (NeC]S). HRMS
(ESI, m/z): calcd for C10H12NS2 [MþH]þ: 210.0406. Found 210.0409.
(ESI, m/z): calcd for C10H12NS2 [MþH]þ: 210.0406. Found 210.0401.
4.4.5. 4,4-Dimethylthiazolidine-2-thione (3a). Colorless crystals,
yield: 67%. Mp 125e128 ꢀC. Lit.16 mp 124.6e125.8 ꢀC. 1H NMR
Acknowledgements
(300 MHz, CDCl3)
6H, 2CH3). 13C NMR (75.5 MHz, CDCl3)
(CH2Cl2),
(cmꢂ1): 3149 (NH), 1490 (NeC]S).
d
: 8.52 (br s, 1H, NH), 4.35 (s, 2H, CH2O), 1.44 (s,
This work was supported by the National Natural Science
Foundation of China (20973013) and the Beijing Natural Science
Foundation (2092022).
d: 188.3, 81.7, 60.2, 26.8. IR
n
4.4.6. 3-Oxa-1-azaspiro[4.6]undecane-2-thione (3b). Colorless crys-
tals, yield, 79%. Mp 110e112 ꢀC. Rf¼0.20 (PE/EA¼4:1). 1H NMR
Supplementary data
(300 MHz, CDCl3) d:9.28(br s,1H, NH), 4.34(s, 2H, CH2),1.98e1.80 (m,
4H, 2CH2CN), 1.66e1.45 (m, 8H, 4CH2). 13C NMR (75.5 MHz, CDCl3)
d:
Copies of 1H and 13C NMR spectra. Supplementary data associ-
ated with this article can be found in the online version, at
InChiKeys of the most important compounds described in this
article.
187.7, 81.3, 66.6, 39.0, 28.7, 22.2. IR (CH2Cl2), n
(cmꢂ1): 3152(NH),1491
(NeC]S). MS (ESI, m/z): 186.0 [MþH]þ, 208.0 [MþNa]þ. HRMS (ESI,
m/z): calcd for C9H16NOS [MþH]þ: 186.0947. Found 186.0952.
4.4.7. 4-Methyl-4-phenylethylthiazolidine-2-thione (3c). Colorless
crystals, yield: 63%. Mp 143e145 ꢀC. Rf¼0.46 (PE/EA¼2:1). 1H NMR
(300 MHz, CDCl3) d: 8.91 (br s,1H, NH), 7.31 (m, 2H, ArHmeta), 7.18 (m,
References and notes
3H, ArHorthoepara), 4.42 (d, J¼9.0 Hz, 1H in CH2S, AB system), 4.29 (d,
J¼9.0 Hz, 1H in CH2S, AB system), 2.68 (m, 2H, CH2Ar), 1.96 (m, 2H,
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CH2C), 1.46 (s, 3H, CH3). 13C NMR (75.5 MHz, CDCl3)
d
: 188.4, 140.2,
128.6, 128.2, 126.3, 80.2, 62.9, 41.6, 30.2, 25.2. IR (CDCl3)
n
(cmꢂ1):
3138 (NH),1490 (NeC]S). MS (ESI, m/z): 222.0 [MþH]þ. HRMS (ESI,
m/z): calcd for C12H16NOS [MþH]þ: 222.0947. Found 222.0946.
4.4.8. 4-Methyl-4-phenyloxazolidine-2-thione (3e). Colorless crys-
tals, yield: 81%. Mp 108e110 ꢀC. 1H NMR (400 MHz, CDCl3)
d: 8.38
(s, 1H, NH), 7.45e7.31 (m, 5H, ArH), 4.63 (d, J¼8.8 Hz, 1H), 4.60 (d,
J¼8.8 Hz, 1H), 1.82 (s, 3H). 13C NMR (101 MHz, CDCl3)
d: 189.2, 141.9,
129.2, 128.4, 124.7, 83.1, 65.1, 26.6. IR (CDCl3)
n
(cmꢂ1): 3142 (NH),
1493 (NeC]S). HRMS (ESI, m/z): calcd for C10H12NOS [MþH]þ:
5. Bachrach, S. M. J. Org. Chem. 2008, 73, 2466e2468.
194.0634. Found 194.0633.
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4.4.9. 5,5-Dimethylthiazolidine-2-thione (4a)17. Colorless crystals,
yield: 20%. Mp 110e112 ꢀC.1H NMR (200 MHz, CDCl3)
d
: 8.40 (br s,1H,
NH), 3.70 (s, 2H, CH2N),1.59 (s, 6H, 2 Me).13C NMR (50 MHz, CDCl3)
201.5, 63.5, 56.9, 28.0. IR (CDCl3)
(cmꢂ1): 3151 (NH),1491 (NeC]S).
8. Yukihito, S.; Masaaki, U.; Ai, S. WO2006051892, 2006.
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d:
n
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4.4.10. 1-Thia-3-azaspiro[4.6]undecane-2-thione (4b). Colorless crys-
tals, yield: 10%. Mp 135e137 ꢀC. 1H NMR (400 MHz, CDCl3)
: 7.91 (s,
1H), 3.68 (s, 2H), 2.18 (dd, J¼14.3, 6.7 Hz, 1H), 1.93 (dd, J¼14.5, 8.6 Hz,
2H), 1.61 (m, 8H). 13C NMR (100 MHz, CDCl3)
: 201.6, 66.1, 62.9, 40.1,
d
d
28.0, 24.0. IR (CDCl3) n
(cmꢂ1): 3150 (NH),1496 (NeC]S). HRMS (ESI,
m/z): calcd for C9H16NS2 [MþH]þ: 202.0718. Found 202.0705.
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4.4.11. 5-Methyl-5-phenylthiazolidine-2-thione (4e). Colorless crys-
tals, yield: 24%. Mp 158e160 ꢀC. 1H NMR (400 MHz, CDCl3)
d: 8.06