
TY  - JOUR
A1  - Cameron, DW 
A1  - Deutscher, KR 
A1  - Feutrill, GI 
A1  - Hunt, DE 
T1  - Synthesis of azaanthraquinones: homolytic substitution of pyridines
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1982
VL  - 35
IS  - 7
SP  - 1451
EP  - 1468
KW  - 
UR  - https://doi.org/10.1071/CH9821451 
N2  - 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). 
ER  -

