Total synthesis of 1,11- and 3,11-diazasteroids

The 2- and 6-methoxy derivatives of 8-aminoquinoline, as well as 5-aminoisoquinoline, condensed with 2-ethoxycarbonylcyclopentanone to give tricyclic intermediates in 86-90% yield. These secosteroids were cyclized in 35-69% yield with polyphosphoric acid to 2-methoxy-1,11-diaza-, 7-methoxy-1,11-diaza-, and 3,11-diaza-1,3,5,7,9,13-gonahexaen-12-ones, respectively. The latter exhibits slight antileukemic activity.