Synthesis of phenazine derivatives for use as precursors to electrochemically generated bases

Abstract

1,6-Disubstituted phenazine derivatives for use as precursors to electrochemically generated bases have been synthesized from readily available starting materials. Reaction of 1,6-dihydroxyphenazine with 1,10-diododecane, 1,11-diiodo-3,6,9-trioxaundecane or (R,R)-(−)-1,2-bis(3-iodopropoxy)cyclohexane gave planar chiral phenazinophanes containing ether-linked bridges; molecular structures of all these compounds have been determined by X-ray crystallography. Substituted 1,6-diaminophenazines were prepared by palladium-mediated amination of 1,6-dichlorophenazine and acylation of 1,6-diaminophenazine followed by reduction. Reaction of 1,6-bis(alkylamino)phenazines with sebacoyl chloride gave planar chiral phenazinophanes containing amide-linked bridges.