Efficient Methods for the Synthesis of 2-Hydroxyphenazine Based on the Pd-Catalyzed N-Arylation of Aryl Bromides

Publikations-Art
Zeitschriftenbeitrag (peer-reviewed)
Autoren
Tietze, M.; Iglesias, A.; Merisor, E.; Conrad, J.; Klaiber, I.; Beifuss, U.
Erscheinungsjahr
2005
Veröffentlicht in
Org. Lett.
Band/Volume
7/8
DOI
0.1021/ol050198y
Seite (von - bis)
1549-1552
Abstract

Substituted diphenylamines can be synthesized by Pd(0)-catalyzed N-arylation using o-nitroanilines and nitro-substituted aryl bromides for a substrate. Cyclization of the diphenylamines by various methods, including the intramol. Pd(0)-catalyzed N-arylation, produces 2-methoxyphenazine which can easily be deprotected to give 2-hydroxyphenazine. This phenazine is required to synthesize methanophenazine, a novel redoxactive cofactor isolated from methanogenic archaea.

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