Synthesis of new steriod sapogenin derivative withp-toluenesulfonamido aziridine by using the intact skeleton of diosgenin
CHEN Zhan-guo, WEN Hua, ZHOU Li-yan, WANG Yin-jie, LI Wen-li, ZHOU Ji-mei
(College of Chemistry and Materials Science, Shaanxi Normal University, Xi′an 710062, Shaanxi, China)
Abstract:
A steriod sapogenin derivative with p-toluenesulfonamido aziridine has been synthesized by using the intact skeleton of diosgenin.Using p-toluenesulfonamide (TsNH2) and N-bromosuccinimide (NBS) as nitrogen and bromine sources, the bromine and p-toluenesulfonamido groups were simultaneously introduced on the carbon-carbon double bonds of 5,6-positions in the diosgenin skeleton in presence of aluminum powder in dichloromethane at room temperature.The intramolecular nucleophilic substitution reaction in diosgenin skeleton was carried out smoothly using K2CO3 as catalyst in acetone to get nearly quantity yield of target compound at room temperature. The structure of target compound was confirmed by 1H NMR, 13C NMR and elemental analysis.
KeyWords:
diosgenin; intact skeleton; aminohalogenation; aziridine
