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16.16.5.1.2 Phenazines by Oxidative Condensation of 4,5-Dihalobenzene-1,2-diamines

DOI: 10.1055/sos-SD-116-01265

Ambhaikar, N. B.Science of Synthesis Knowledge Updates, (20202196.

A one-pot, scalable synthesis of a series of fluorescent 7,8-dihalophenazine-2,3-diamines 8 involves oxidative condensation of 4,5-dihalobenzene-1,2-diamines 7 under aqueous conditions promoted by iron(III) chloride (Scheme 5).[‌27‌] The resulting phenazinediamines offer an opportunity as intermediates to construct polyfunctional phenazines and extended polyheteroacenes. The equimolar amount of acetone suppresses the formation of undesired hydroxylation products that may typically arise otherwise under aqueous conditions during the oxidation process and thereby allows for selective formation of the 7,8-dihalo-2,2-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]phenazine derivatives 8 in good to excellent yields. Formation of both undesired phenazine-2,3-amines and their related hydroxylated derivatives can be completely avoided under these optimized conditions. The methodology has been demonstrated up to a few grams and it is specific for 4,5-dihalobenzene-1,2-diamines 7 as substrates.

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