Ring contracting sulfur extrusion from oxidized phenothiazine ring systems

Molecules. 2008 Jun 12;13(6):1345-52. doi: 10.3390/molecules13061345.

Abstract

Lithium, used in conjunction with sodium metal, produces a high yield of carbazole when reacted with phenothiazine-5-oxide or phenothiazine-5,5-dioxide. A high yield of 9-ethylcarbazole is also produced when these reagents react with 10-ethylphenothiazine, 10-ethylphenothiazine-5-oxide, and 10-ethylphenothiazine-5,5-dioxide. Degassed Raney nickel produces carbazole in high yield when reacted with phenothiazine and phenothiazine-5-oxide. A moderate yield of 9-ethylcarbazole is produced when n-butyllithium is reacted with 10-ethylphenothiazine-5-oxide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbazoles / chemical synthesis
  • Lithium
  • Nickel
  • Phenothiazines / chemistry*
  • Sulfur

Substances

  • Carbazoles
  • Phenothiazines
  • Sulfur
  • Nickel
  • Lithium
  • phenothiazine