- N-Heterocyclization of naphthylamines with 1,2- And 1,3-Diols catalyzed by an iridium Chloride/BINAP system
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Benzoquinoline derivatives were successfully synthesized by iridium-catalyzed N-heterocyclization of naphthylamines with diols. For instance, the reaction of 1-naphthylamine with 1,3-propanediol catalyzed by IrCl3 combined with BINAP as a ligand produced 7,8-benzoquinoline in quantitative yield. The VV-heterocyclization reaction was found to be markedly influenced by the ligands employed. Benzoindoles were also synthesized by the same strategy from napthylamines with 1,2-diols. A reaction mechanism for the N-heterocyclization of naphthylamines with 1,3-diols by IrCl3 was proposed.
- Aramoto, Hiroomi,Obora, Yasushi,Ishii, Yasutaka
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scheme or table
p. 628 - 633
(2009/06/28)
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