Citation: Tang Lei, Yang Maoxiang, Ma Fuli, Li Xueqiang, Wei Mengxue. Syntheses of Artemisone-aminodithioformate Hybrid Compounds[J]. Chemistry, ;2017, 80(9): 884-887. shu

Syntheses of Artemisone-aminodithioformate Hybrid Compounds

Tang Lei ¹ ,
Yang Maoxiang ¹ ,
Ma Fuli ^1,, ,
Li Xueqiang ^1,2 ,
Wei Mengxue ^1,2,,

1.
College of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021
2.
Ningxia Engineering Research Center for Natural Medicines, Yinchuan 750021

Corresponding author: Ma Fuli, lixq@nxu.edu.cn Wei Mengxue, weimengxue@nxu.edu.cn
Received Date: 18 March 2017
Accepted Date: 11 May 2017

Figures(1)

A practical preparation of artemisone-aminodithioformate hybrid compounds was achieved from dihydroartemisinin and thiomorpholine. The dihydroartemisinin was treated with oxalyl chloride followed by mixing the mixture with a solution of thiomorpholine in dichloromethane, efficiently affording the artemisinin-thiomorpholine complex. Then oxidation of the raw mixture with hydrogen peroxide in the presence of sodium tungstate gave the artemisone 1 with 48% yield for three steps. The artemisone 1 was alkylated with a silyl protected 6-iodo-1-hexanol, then desilylation and iodination of the alkylate compound successfully delivered the corresponding iodide 2α, and the total yield for these three steps was 22.1%. Finally, introduction of the piperazidines into the artemisone motif was realized with carbon disulphide as the linkage, where four artemisone-aminodithioformate hybrid compounds (3a~3d) were obtained from a triethylamine promoted one-pot reaction of iodide 2α, piperazidine and carbon disulphide from room temperature to reflux. The structures of all the synthetic compounds are identified by ¹H NMR, ¹³C NMR, IR and HR-ESI-MS.
- Dihydroartemisinin,
- Synthesis,
- Artemisone,
- Aminodithioformate
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