The 1,3-Diazabiphenylene system. synthesis, chemistry, and incorporation into a linearly extended purine analogue

117 p.Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1984.The first synthesis of the 1,3-diazabiphenylene ring system by cobalt-catalyzed cooligomerization of a novel diethynylpyrimidine and bis(trimethylsilyl)acetylene is described. This diazabiphenylene is found to undergo an unusual structural rearrangement on treatment with acid in methanol, providing a substituted isoquinoline. Progress toward the synthesis of the dimensional probe, lin-bcb-adenine, incorporating the 1,3-diazabiphenylene skeleton, is summarized, and the synthesis of a pyrimido{6,5-i}imidazo{4,5-g}cinnoline, via a heteroaromatic cross coupling reaction, is discussed.U of I OnlyRestricted to the U of I community idenfinitely during batch ingest of legacy ETD