Application of FeCl3/Diorganyl Diselenides to Cyclization of o-Alkynyl Anilines: Synthesis of 3-Organoselenyl-(N-methyl)indoles

被引：18

作者：

Speranca, Adriane ^{[1
]}

Godoi, Benhur ^{[2
]}

Menezes, Paulo Henrique ^{[3
]}

Zeni, Gilson ^{[1
]}

机构：

[1] Univ Fed Santa Maria, CCNE, Lab Sintese Reatividade Avaliacao Farmacol & Toxi, BR-97105900 Santa Maria, RS, Brazil

[2] Univ Fed Fronteira Sul, BR-97900000 Cerro Largo, RS, Brazil

[3] Univ Fed Pernambuco, Dept Quim Fundamental, BR-50670901 Recife, PE, Brazil

来源：

SYNLETT | 2013年 / 24卷 / 09期

关键词：

indole; iron salt; cyclization; selenium; LITHIUM-SELENIUM EXCHANGE; CROSS-COUPLING REACTIONS; BIOLOGICAL EVALUATION; DIPHENYL DISELENIDE; DERIVATIVES; ARYLATION; 3-SELENYLINDOLES;

D O I：

10.1055/s-0033-1338427

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this manuscript we described the FeCl3/diorganyl diselenides promoted intramolecular cyclization of o-alkynyl anilines, as an alternative for the construction of functionalized 3-organoselenyl indoles. The cyclization reactions proceeded smoothly at room temperature in the presence of air giving the 3-organoselenyl indoles in good yields. Additionally, the 3-organoselenyl indoles proved to be quite useful as synthetic intermediates for the construction of more functionalized indole units through a selenium-lithium exchange reaction followed by trapping the lithium intermediate with different electrophiles.

引用

页码：1125 / 1132

页数：8