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. shu

Synthesis of New Thiazine and Thiosemicarbazone Derivatives from D-Xylose

New Drug Research & Development Center, Zhenzhou University, Zhengzhou 450052

Received Date: 16 June 2006

Fund Project: We are grateful to the National Natural Science Foundation of China (No. 20472075) for financial support of this work.

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.
- Thiourea,
- aminothiourea,
- thiazine,
- D-xylose,
- synthesis
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