Reaction of chlorodithiophosphoric acid pyridiniumbetaine with adamantane derivatives containing amino group

Reactions of chlorodithiophosphoric acid pyridiniumbetaine, py.PS2Cl (I) with 1-aminoadamantane (amantadine, Am) and 1-amino-3,5-dimethyladamantane (memantine, Mem), 1-(adamant-1-yl)ethylamine (rimantadine, Rim), and 1-aminomethyladamantane (amAd) were studied. New compounds – N,N′,N′′,N′′′-tetrakis(adamant-1-yl)trithiophosphoric acic tetraamide (II), N,N′,N′′,N′′′-tetrakis(3,5-dimethyladamant-1-yl)trithiophosphoric acid tetraamide (III), chlorodithiophosphoric acid 1-(adamant-1-yl)ethylamide pyridiniumbetaine (IV), pyridinium salt of 1,3-bis(adamant-1-yl)ethane-2,4-mercapto-2,4-dithioxo-1,3-diaza-2λ5,4λ5-diphosphetidine (V), N,N′,N′′,N′′′-tetrakis(adamant-1-ylmethyl)trithiophosphoric acid tetraamide (VI), and pyridinium salt of 1,2-bis(adamant-1-ylmethane)-4-mercapto-2,4-dithioxo-1-aza-3-thia-2λ5,4λ5-diphosphetidine (VII) – were prepared and characterized either/or by 31P NMR and infrared spectroscopy, the substances II a IV by X-ray diffraction analysis, III, V, VI, VII by MALDI TOF MS.

Reactions of chlorodithiophosphoric acid pyridiniumbetaine, py.PS2Cl, with 1-aminoadamantane (amantadine, Am) and 1-amino-3,5-dimethyladamantane (memantine, Mem), 1-(adamant-1-yl)ethylamine (rimantadine, Rim), and 1-aminomethyladamantane (amAd) were studied. New compounds of the trithiophosphoric acic tetraamide, diphosphetidine or azathiadiphosphetidine (in the form of pyridinium salts) types were prepared and characterized either/or by 31P NMR, MALDI TOF MS and infrared spectroscopies or X-ray diffraction analysis.Figure optionsDownload as PowerPoint slide