N-Heterocyclization of Naphthylamines with 1,2-and 1,3-Diols Catalyzed by an Iridium Chloride/BINAP System

被引：77
|
作者：
Aramoto, Hiroomi
Obora, Yasushi
Ishii, Yasutaka [1 ]
机构：
[1] Kansai Univ, Fac Chem Mat & Bioengn, Dept Chem & Mat Engn, Osaka 5648680, Japan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 02期
关键词：
PRIMARY ALCOHOLS; KETONES; CYCLIZATION; QUINOLINES;
D O I：
10.1021/jo801966u
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：628 / 633
页数：6
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