Carcinogenic nitrogen compounds. Part LXI. The Skraup reaction with diamines derived from acenaphthene and anthracene

Abstract

1,5-Diaminoanthracene and 5,6-diaminoacenaphthene readily undergo double Skraup cyclisation to benzo[1,2-h : 4,5-h′]diquinoline and dipyrido[2,3-e : 2,3-h]acenaphthene. Under the same conditions however, 3,6-diaminoacenaphthene gave only a monocyclisation product, 3-aminoindeno[1,7-gh]quinoline, and 3,8-diaminoacenaphthene remained pratically unchanged; this suggests bond fixation in the aromatic framework of these two diamines. N.m.r. spectra were used to ascertain structures of acenaphthene intermediates.