A Synthetic Route to 2-Alkyl Indoles via Thiophenol-Mediated Ring-Opening of N-Tosylaziridines Followed by Copper Powder-Mediated C-N Cyclization/Aromatization

被引：39

作者：

Sayyad, Masthanvali ^{[1
]}

Nanaji, Yerramsetti ^{[1
]}

Ghorai, Manas K. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 24期

关键词：

PALLADIUM-CATALYZED REACTIONS; ACTIVATED AZIRIDINES; BOND FORMATION; ROOM-TEMPERATURE; DIAZO-COMPOUNDS; DOMINO REACTION; H ACTIVATION; ARYL IODIDES; CYCLIZATION; 2H-AZIRINES;

D O I：

10.1021/acs.joc.5b02251

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple strategy for the syntheses of 2-alkyl indoles via regioselective ring-opening of 2-(2-haloaryl)-3-alkyl-N-tosylaziridines with thiophenol, followed by copper powder-mediated intramolecular C-N cyclization and subsequent aromatization by the elimination of thiophenol, with good yields is described. Utilizing this protocol, 2-carboxyindole has been synthesized easily.

引用

页码：12659 / 12667

页数：9

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