Polyaza heterocycles. Part 3. Halogenation of 1-substituted quinoxalino[2,3-c]cinnolines: mechanistic implications
Abstract
Since it has been proposed that halogenation of quinoxalino[2,3-c]cinnolines at C-10, using hydrogen chloride or bromide in chloroform, occurs through initial protonation of the substrate at N-12, attempts have been made to inhibit this protonation by the introduction of an additional substituent at C-1. Where this substituent is chloro, bromo or methyl, chlorination still occurs preferentially at C-10, although the yield and the reaction rate decrease along the series, lending weight to the mechanistic proposal.