N-heterocyclization of naphthylamines with 1,2- and 1,3-diols catalyzed by an iridium chloride/BINAP system.
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 IrCl(3) 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 IrCl(3) was proposed.
Aramoto
Hiroomi
H
Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering & High Technology Research Center, Kansai University, Suita, Osaka 564-8680, Japan.
Obora
Yasushi
Y
Ishii
Yasutaka
Y
D000438:Alcohols / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry; D007495:Iridium / Q000737:chemistry*; D009281:Naphthalenes / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry
D000438:Alcohols; D000588:Amines; C406943:BINAP, 2-naphthol; D002712:Chlorides; D006571:Heterocyclic Compounds; D007211:Indoles; D009281:Naphthalenes; D011804:Quinolines; C538735:iridium chloride; D007495:Iridium; C030374:indole; C037219:quinoline