
%0 Journal Article
%A Cameron, DW 
%A Deutscher, KR 
%A Feutrill, GI 
%A Hunt, DE 
%T Synthesis of azaanthraquinones: homolytic substitution of pyridines
%J Australian Journal of Chemistry
%D 1982/07/01
%V 35
%N 7
%P 1451-1468
%K 
%R https://doi.org/10.1071/CH9821451
%U https://www.publish.csiro.au/paper/CH9821451 
%X Synthesis of specific di- and tri-hydroxyazaanthraquinones by Friedel-Crafts procedures is limited by orientational ambiguity and by the lack of reactivity of pyridine derivatives in electrophilic acylation processes; however, suitable pyridines have been made to undergo radical benzoylation and benzylation at unsubstituted positions 2, 4 and 6. In particular, derivatives of pyridine-3-carbo-nitrile have been benzoylated at positions 2 and 4. Ring closure by intramolecular Houben-Hoesch reaction has then led to specifically substituted 1-and 2-azaanthraquinones and thence to the antibiotic bostrycoidin (1). 
