| Abstract: | A new general reaction of wide synthetic interest, involving homolytic δ-aminoalkylation of quinoxaline in acidic medium, is described. Primary and secondary alkylamines, through the corresponding N-chloroamines, and tertiary alkylamines, through the corresponding N-oxides, are used. The mechanism of the reaction, involving intramolecular hydrogen abstraction by amino radical cations, and the unusual selectivity are discussed in terms of nucleophilic character of the alkyl radicals and of polar effects in the aromatic substitution. |
