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Ring contracting sulfur extrusion from oxidized phenothiazine ring systems.

Steven C Farmer1, Seth H Berg

  • 1Department of Chemistry, Sonoma State University, 1801 East Cotati Avenue, Rohnert Park, California 94928, USA. farmers@sonoma.edu

Molecules (Basel, Switzerland)
|July 4, 2008
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Summary

Lithium and sodium metal efficiently synthesize carbazole derivatives from phenothiazine oxides. Degassed Raney nickel also yields carbazole, while n-butyllithium produces 9-ethylcarbazole.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Phenothiazine derivatives are important in various chemical applications.
  • Efficient synthesis routes for carbazole and its derivatives are of significant interest.

Purpose of the Study:

  • To explore novel synthetic pathways for carbazole and 9-ethylcarbazole.
  • To evaluate the efficacy of lithium, sodium metal, and Raney nickel in these transformations.

Main Methods:

  • Reaction of phenothiazine-5-oxide and phenothiazine-5,5-dioxide with lithium and sodium metal.
  • Reaction of 10-ethylphenothiazine, 10-ethylphenothiazine-5-oxide, and 10-ethylphenothiazine-5,5-dioxide with lithium and sodium metal.
  • Reaction of phenothiazine and phenothiazine-5-oxide with degassed Raney nickel.
  • Reaction of 10-ethylphenothiazine-5-oxide with n-butyllithium.

Main Results:

  • High yields of carbazole were obtained from phenothiazine-5-oxide or phenothiazine-5,5-dioxide using lithium and sodium metal.
  • High yields of 9-ethylcarbazole were achieved with various ethylphenothiazine precursors using lithium and sodium metal.
  • Degassed Raney nickel effectively produced carbazole from phenothiazine and phenothiazine-5-oxide.
  • Moderate yields of 9-ethylcarbazole were observed with n-butyllithium and 10-ethylphenothiazine-5-oxide.

Conclusions:

  • Lithium and sodium metal offer a high-yield route to carbazole and 9-ethylcarbazole from specific phenothiazine precursors.
  • Degassed Raney nickel is a viable reagent for carbazole synthesis.
  • n-Butyllithium can be used for moderate synthesis of 9-ethylcarbazole.