Phenanthridine

• Benzo [ c] quinoline
• 3,4- Benzoquinolin

Light brown crystalline solid

Fixed

104-107 ° C

349 ° C at 1025 hPa

Soluble in methanol

Risk

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Phenanthridine is a chemical compound from the group of nitrogen-containing heterocycles.

Production and representation

Phenanthridine was first synthesized in 1889 by Jules Pictet and H. Amé January Ankersmit from benzalaniline by pyrolysis in the glow tube. Its derivatives are naturally occurring in Amaryllidoideae.

In the Pictet -Hubert reaction, (1899 ) the compound formed by the reaction of a 2- aminobiphenyl -formaldehyde adduct ( a N-acyl -o- xenylamin ) with zinc chloride at elevated temperatures. The reaction conditions were used in 1931 by Morgan and Walls by replacement of metal by using phosphorus oxychloride and nitrobenzene ( nitrobenzene ) as the solvent. For this reason, the reaction is also called Morgan Walls reaction.

The reaction is similar to Bishler -Napieralski reaction and Pictet -Spengler reaction. The production beginning with phenanthraquinone, N- methylcarbazole, Fluorenonoxim or Phenanthridonen is possible.

Halogenated Benzylarylaminen phenanthridine and its derivatives can be synthesized via aryne intermediate.

Properties

Phenanthridine is a light brown crystalline solid. Phenanthridine and its derivatives are tertiary bases and form acid mono-acid salts.

Use

Phenanthridine alkaloids is the basic structure of some (for example, fagaronine, more hydrobenzo [ c] phenanthridines ), drugs (e.g. isometamidium ) and other chemical compounds (e.g., ethidium bromide ) dar.