Heterocyclic imines and amines. Part 18. Conversion of o-cyanobenzyl cyanide into isoquinoline, benzylisoquinoline, and azachrysene products

Abstract

With sodamide in formamide, o-cyanobenzyl cyanide dimerises in the two ways possible: it also adds formamide to yield 1-amino-3-formamidoisoquinoline (2). Each dimer undergoes cycloisomerisation: thus 1-amino-3-o-cyanobenzyl-4-cyanoisoquinoline (5a) and 6,11-diamino-12-cyanobenzo[c]phenanthridine (9) were isolated. o-Cyanobenzyl cyanide with sodium methoxide afforded (5a) very slowly in methanol but much more rapidly in dimethyl sulphoxide–methanol.