Substitution reactions of phenanthro[9,10-d]triazole with benzyl chlorides

Article abstract of DOI:10.1002/jhet.5570350218

The reaction of the potassium salt of phenanthro[9,10-d]triazole and benzyl chloride gave 2-(benzyl)-2H-phenanthro[9,10-d]triazole (2a) in 15% yield. The other regio-isomer, 1-(benzyl)-1H-phenanthro[9,10-d]-triazole (1a), was obtained as a by-product in 3.9% yield. Similar reactions with benzyl chlorides having a methyl, a chloro or a nitro group on the aromatic ring gave the corresponding two products, 1b-j and 2b-j. In all cases, 2b-j were major products in yields of 14-62%, 1b-j were minor ones in yields of 1.4-7.6%. The structures of the isomers were confirmed by X-ray crystal analyses.