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.

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收藏

页码：628 / 633

页数：6

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