The 1,3-Diazabiphenylene system. synthesis, chemistry, and incorporation into a linearly extended purine analogue
D'alarcao, Marc M.
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https://hdl.handle.net/2142/70233
Description
Title
The 1,3-Diazabiphenylene system. synthesis, chemistry, and incorporation into a linearly extended purine analogue
Author(s)
D'alarcao, Marc M.
Issue Date
1984
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Abstract
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.
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