引用本文:
Xiao Ming JI, He Ping SUN, Hai Wei XU, Hong Min LIU. Synthesis of New Thiazine and Thiosemicarbazone Derivatives from D-Xylose[J]. Chinese Chemical Letters,
2006, 17(12): 1563-1565.
Citation: Xiao Ming JI, He Ping SUN, Hai Wei XU, Hong Min LIU. Synthesis of New Thiazine and Thiosemicarbazone Derivatives from D-Xylose[J]. Chinese Chemical Letters, 2006, 17(12): 1563-1565.
Citation: Xiao Ming JI, He Ping SUN, Hai Wei XU, Hong Min LIU. Synthesis of New Thiazine and Thiosemicarbazone Derivatives from D-Xylose[J]. Chinese Chemical Letters, 2006, 17(12): 1563-1565.
Synthesis of New Thiazine and Thiosemicarbazone Derivatives from D-Xylose
摘要:
1, 2-O-Isopropylidene-5-O-p-toluenesulfonyl-α-D-erythro-pentofuranos-3-ulose 1 was treated with thiourea and aminothiourea to give a D-ribose derivative 2 bearing a 2-amino 1, 3-thiazine ring and a thiosemicarbazone derivative 5, respectively. 2 was acylated with Ac2O and propandioic acid to afford two acylation derivatives 3 and 4, respectively. Reduction of 5 with NaBH4 in methanol produced a hydrothiosemicarbazone derivative 6. The absolute configuration of 2 was confirmed by X-ray crystallographic analysis. The structures of all products were elucidated by IR, NMR and HRMS spectra.
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关键词:
- Thiourea
- / aminothiourea
- / thiazine
- / D-xylose
- / synthesis
English
Synthesis of New Thiazine and Thiosemicarbazone Derivatives from D-Xylose
Abstract:
1, 2-O-Isopropylidene-5-O-p-toluenesulfonyl-α-D-erythro-pentofuranos-3-ulose 1 was treated with thiourea and aminothiourea to give a D-ribose derivative 2 bearing a 2-amino 1, 3-thiazine ring and a thiosemicarbazone derivative 5, respectively. 2 was acylated with Ac2O and propandioic acid to afford two acylation derivatives 3 and 4, respectively. Reduction of 5 with NaBH4 in methanol produced a hydrothiosemicarbazone derivative 6. The absolute configuration of 2 was confirmed by X-ray crystallographic analysis. The structures of all products were elucidated by IR, NMR and HRMS spectra.
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Key words:
- Thiourea
- / aminothiourea
- / thiazine
- / D-xylose
- / synthesis
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