1,3-Heterazolidines-2-heterounsaturated compounds derived from ephedrines

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• 作者：Alejandro Cruz ; Rosalinda Contreras ; Itzia I. Padilla-Mart&#xed ; nez and Minerva Juá ; rez-Juá ; rez
• 刊名：Tetrahedron: Asymmetry
• 出版年：2006
• 出版时间：19 June 2006
• 年：2006
• 卷：17
• 期：10
• 页码：1499-1505
• 全文大小：248 K

文摘

Herein, a direct and easy method for preparing 2-oxo-, 2-thione- or 2-imine-1,3-heterazolidines derived from ephedrines and norephedrines are reported. The method is based on solvent free heating of ephedrines with oxocyanate or thiocyanate salts (180–200 °C). In the reactions with potassium oxocyanate in refluxing ethanol, it was possible to isolate ureidic derivatives. The structure and stereochemistry of the compounds were determined by ¹H, ¹³C NMR, IR spectroscopies and mass spectrometry. Ureidic derivatives, cis-1,5-dimethyl-4-phenyl-imidazolidine-2-thione and trans-4-methyl-5-phenyl-thiazolidine-2-one are new compounds. Ephedrineurea, cis-1,5-dimethyl-4-phenyl-imidazolidine-2-thione and trans-4-methyl-5-phenyl-thiazolidine-2-one were also studied by X-ray diffraction.