Journal of Organic Chemistry p. 2462 - 2468 (1985)
Update date:2022-08-17
Topics:
Gibson, Katharine J.
d'Alarcao, Marc
Leonard, Nelson J.
4-Methoxy-1-azabiphenylene and 1-methoxy-2-azabiphenylene have been synthesized from the appropriate precursor diethynylmethoxypyridines via cobalt-catalyzed cooligomerization with bis(trimethylsilyl)acetylene.When 4-methoxy-1,3-diazabiphenylene was transformed into 1,3-dimethoxyisoquinoline in methanolic sodium methoxide at reflux overnight, 1-methoxy-2-azabiphenylene required longer reflux time and 4-methoxy-1-azabiphenylene required forcing conditions for transformations to occur.The transformations product from the latter was shown to be 1,5-dimethoxy-2-benzazocine and that from the former was established by independent synthesis to be 3-methoxy-1-((E)-2-methoxyethenyl)isoquinoline.The impressive disparity in the products obtained from the methoxydiazabiphenylene and the two methoxyazabiphenylenes can be rationalized by consideration of the locus of methanol addition and sequential electrocyclic reactions.
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