POLYAZAPOLYCYCLICS BY CONDENSATION OF ALDEHYDES WITH AMINES .2. FORMATION OF 2,4,6,8,10,12-HEXABENZYL-2,4,6,8,10,12-HEXAAZATETRACYCLO[5.5.0.0/5.9/0/3,11]DODECANES FROM GLYOXAL AND BENZYLAMINES

The condensation of glyoxal with benzylamine leads to 2, 4, 6, 8, 10, 12-hexabenzyl-2, 4, 6, 8, 10, 12-tetraazatetra-cyclo[5.5.0.05.9.03, 11]dodecane (2a) in solvents such as acetonitrile or methanol with formic acid catalyst. Six phenyl-substituted derivatives of 2a have been prepared and the scope of the reaction has been examined. Intermediates l, 2,-bis(benzylamino)-l, 2-ethanediol (6) and N, N’-dibenzyl-1, 2-ethanediimine (7) have been prepared and the mechanism of their conversion to 2a is discussed. In the absence of acid catalysts, the glyoxal hemiacetal derivative 2, 3-dihydroxyl, 4-dioxane reacts with benzylamine or 4-pyridylmethylamine in acetonitrile solvent to produce 9, 10-bis(arylmethyl)-9, 10-diaza-l, 4, 5, 8-tetraoxaperhydroanthracenes 13a, b. © 1990, American Chemical Society. All rights reserved.