Efficient methods for the synthesis of 2-hydroxyphenazine based on the Pd-catalyzed N-arylation of aryl bromides.
[reaction: see text] 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 intramolecular 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.
Tietze
Mario
M
Bioorganische Chemie, Institut für Chemie, Universität Hohenheim, Garbenstrasse 30, D-70599 Stuttgart, Germany.
Iglesias
Alberto
A
Merisor
Elena
E
Conrad
Jürgen
J
Klaiber
Iris
I
Beifuss
Uwe
U
D001105:Archaea / Q000737:chemistry / Q000378:metabolism; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D003500:Cyclization; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010619:Phenazines / Q000138:chemical synthesis* / Q000378:metabolism
D006842:Hydrocarbons, Brominated; D010619:Phenazines; D010165:Palladium