Access to functionalized 3-amino-benzothiophenes using keteniminium intermediates. Issue 47 (25th November 2015)

• Record Type: Journal Article
• Authors: Lumbroso, Alexandre; Behra, Julien; Kolleth, Amandine; Dakas, Pierre-Yves; Karadeniz, Ulfet; Catak, Saron; Sulzer-Mossé, Sarah; De Mesmaeker, Alain
• Is Part Of: Tetrahedron letters. Volume 56:Issue 47(2015)
• Page Start: 6541
• Page End: 6545
• Publication Date: 2015-11-25
• Subjects: Keteniminium salts -- Electrocyclization -- Amino-benzothiophene -- DFT calculations; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.09.103
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: We describe a very efficient access to 3-aminobenzothiophenes using substituted phenylthioacetamides via a 6π-electrocylization of the corresponding keteniminium intermediates. The ease of this electrocyclization allows the use of N -allyl and N -diallyl protecting groups leading to the corresponding primary or secondary amines after mild deprotection.