Synthesis of New Thiazine and Thiosemicarbazone Derivatives from D-Xylose  

作　　者：Xiao Ming JI He Ping SUN Hai Wei XU Hong Min LIU 

机构地区：[1]New Drug Research ＆ Development Center, Zhenzhou University, Zhengzhou 450052

出　　处：《Chinese Chemical Letters》2006年第12期1563-1565,共3页中国化学快报（英文版）

基　　金：the National Natural Science Foundation of China(No.20472075)for financial support of this work.

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 Ac20 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.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 Ac20 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.

关 键 词：THIOUREA aminothiourea THIAZINE D-XYLOSE synthesis. 

分 类 号：O623.542[理学—有机化学] O626[理学—化学]