Studies on the reaction of benzoyl peroxide with NN-disubstituted aromatic amines and related compounds. Part V. Preparation of 5,11-disubstituted 5,6,11,12-tetrahydrophenhomazines from α-diamines

Abstract

NN′-Dialkyl-NN′-diaryl- and NNN′N′-tetra-aryl-methanediamines, when treated with weak acids in chloroform solution, afford 5,11-disubstituted 5,6,11,12-tetrahydrophenhomazines. The reaction, which is of preparative value, appears to involve decomposition of the α-diamine to give an iminium ion, which then attacks a second molecule of the diamine. In the presence of excess of NN-dimethylaniline the latter is attacked in the para-position by the iminium ion. 1,2,3,4-Tetrahydro-1,6-dimethyl-3-p-tolylquinazoline, when treated with methyl bromide, also yields a phenhomazine of the same type.