Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 2, Pages 628-633Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo801966u
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- Ministry of Education, Culture, Sports, Science and Technology, Japan
- Ministry of Education, Culture, Sports, Science and Technology
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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 N-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.
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