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Synlett 2009(4): 648-650  
DOI: 10.1055/s-0028-1087918
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Novel One-Pot, Four-Component Synthesis of 3-Alkyldithiocarbonyl-oxa­zolidines from Aminoethanols, Ketones, Carbon Disulfide, and Halides

Fang-bin Hana,b, Ze-mei Ge*b, Tie-ming Chengb, Run-tao Li*a,b
a State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, P. R. of China
b School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. of China
Fax: +86(10)82716956; e-Mail: lirt@mail.bjmu.edu.cn;
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Publication History

Received 30 September 2008
Publication Date:
16 February 2009 (online)

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Abstract

A novel one-pot, four-component synthesis of 3-alkyl­dithiocarbonyloxazolidine derivatives from aminoethanols, ketones, carbon disulfide, and halides was developed. A series of substituted 3-alkyldithiocarbonyloxazolidine derivatives were synthesized in excellent yields utilizing this newly developed method.

Key words

four-component synthesis - aminoethanol - 3-alkyl­dithiocarbonyloxazolidines - dithiocarbamate - anhydrous K3PO4

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Li, R. T. unpublished results.

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Typical Procedure for the Synthesis of Compounds 3
To a solution of aminoethanol (2 mmol) in acetone (10 mL) was added anhyd K3PO4 (4 mmol), and the reaction mixture was stirred at r.t. for 30 min. CS2 (4 mmol) was then added dropwise. The reaction mixture was stirred for an additional 20 min, and halide (2 mmol) was then added. Stirring was continued at r.t. until the reaction was completed (monitored by TLC). The precipitate was filtered and washed with acetone. The solvent was evaporated under reduced pressure, and the residue was purified by chromatography on a silica gel column (PE-EtOAc) to give the desired compounds 3.
Selected Data for Compound 3f
White solid; mp 104-106 ˚C. ¹H NMR (300 MHz, CDCl3): δ = 1.83 (s, 6 H), 2.81 (t, J = 7.8 Hz, 2 H), 3.30 (t, J = 8.1 Hz, 2 H), 3.82 (t, J = 6.3 Hz, 2 H), 4.06 (t, J = 6.3 Hz, 2 H), 7.26-7.49 (m, 10 H). MS (EI, 70 eV): m/z (%) = 396 (6) [M]+, 204 (7), 193 (7), 177 (55), 165 (15), 144 (57), 118 (25), 86 (100). Anal. Calcd for C23H26N2OS2: C, 66.63; H, 6.10; N, 7.06. Found: C, 66.71; H, 6.10; N, 7.03.
Selected Data for Compound 3h Light yellow oil. ¹H NMR (300 MHz, CDCl3): δ = 1.30 (t, J = 7.2 Hz, 3 H), 1.83 (s, 6 H), 3.93 (t, J = 6.3 Hz, 2 H), 4.10 (t, J = 6.3 Hz, 2 H), 4.13 (s 2 H), 4.23 (q, J = 7.2 Hz, 2 H). Anal. Calcd for C10H17NO3S2: C, 45.60; H, 6.51; N, 5.32. Found: C, 45.45; H, 6.57; N, 5.36.