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Formation of Indoles, Dihydroisoquinolines, and Dihydroquinolines by Ruthenium-Catalyzed Heterocyclizations

Alejandro Varela-Fernández, Jesús A. Varela, Carlos Saá*

*Departamento de Química Orgánica y Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS), Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain, Email: carlos.saausc.es

A. Varela-Fernández, J. A. Varela, C. Saá, Synthesis, 2012, 44, 3285-3295.

DOI: 10.1055/s-0032-1316539 (free Supporting Information)


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Abstract

Indoles, dihydroisoquinolines, and dihydroquinolines were efficiently prepared by ruthenium-catalyzed heterocyclizations of aromatic homo- and bis-homopropargyl amines or amides in the presence of pyridine. These regioselective 5-endo and 6-endo cyclizations most probably occur by nucleophilic trapping of key ruthenium-vinylidene intermediates.

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Key Words

heterocyclizations, indoles, isoquinolines, quinolones, ruthenium, vinylidenes


ID: J66-Y2012-3460