Collection of Czechoslovak Chemical Communications - digital archive 

Abstract

Reactions of 5-methylphenanthridinium iodide (I) with oxygen, nitrogen, and carbon nucleophiles, respectively, were studied. 5-Methylphenanthridinium iodide (I) yielded in the basic aqueous medium 5-methyl-6-phenanthridone (II) and 5,6-dihydro-5-methylphenanthridine (III). By NMR spectroscopy in the D₂O-CD₃CN solution 5,6-dihydro-6-deuteroxy-5-methylphenanthridine (IVb) (pseudobase) was observed as an immediate unstable product. 5-Methylphenanthridinium iodide (I) gave the corresponding adducts with methoxide and ethoxide anions, morpholine, piperidine, pyrrolidine, cyanide anion and acetone. Their structure was determined by IR, ¹H and ¹³C NMR spectroscopy. Reactions of 5,6-dihydro-5-methyl-6-morpholinophenanthridine (VII) were followed by NMR spectroscopy. Morpholino adduct VII gave in the CD₃CN-D₂O solution pseudobase (IVb) and its products of disproportionation: oxophenanthridine II and dihydrophenanthridine III. Treatment of 5,6-dihydro-5-methyl-6-morpholinophenanthridine (VII) with H₂O/D₂O in (CH₃)₂CO/(CD₃)₂CO led to CH₃COCH₂-/CD₃COCD₂- adduct XIa/XIb formation, respectively.