Reactions of 5-methylphenanthridinium iodide with nucleophiles and reaction products conversion.
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Reactions of 5-methylphenanthridinium iodide with nucleophiles
and reaction products conversion.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. H-1 and C-13 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.