Reactions of 5-Methylphenanthridinium Iodide with Nucleophiles and Reaction Products Conversion
- 1 January 1993
- journal article
- Published by Institute of Organic Chemistry & Biochemistry in Collection of Czechoslovak Chemical Communications
- Vol. 58 (2) , 395-403
- https://doi.org/10.1135/cccc19930395
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.Keywords
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