Multiple Diamine-Dialdehyde Condensations. Synthesis of Heterocyclic Dodecalenes.

Article abstract of DOI:10.1021/jo00328a005

The diamine-dialdehyde condensation of biphenyl-2,6,2',6'-tetracarbaldehyde (6) and 2,2'-diaminobiphenyl (3) in benzene (TsOH catalyst) gave the tetra Schiff base 9,15,24,30-tetraazahexabenzododecalene (4). 10,14,25,29-Tetraazadodecalene (5) was prepared analogously from 2,6,2',6'-tetraaminobiphenyl (7) and biphenyl-2,2'-dicarbaldehyde (2).The condensation of 6 with o-phenylenediamine and with 2,3-diaminonaphthalene afforded "hydride shift" products 10 and 13.The geometries of 4 and 5 are briefly discussed.