Access to functionalized 3-amino-benzothiophenes using keteniminium intermediates

Lumbroso, Alexandre; Behra, Julien; Kolleth, Amandine; Dakas, Pierre-Yves; Karadeniz, Ulfet; ÇATAK, ŞARON; Sulzer-Mossé, Sarah; De Mesmaeker, Alain

doi:10.1016/j.tetlet.2015.09.103

Access to functionalized 3-amino-benzothiophenes using keteniminium intermediates

Lumbroso A., Behra J., Kolleth A., Dakas P., Karadeniz U., ÇATAK Ş., ...Daha Fazla

Tetrahedron Letters, cilt.56, sa.47, ss.6541-6545, 2015 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 56 Sayı: 47
Basım Tarihi: 2015
Doi Numarası: 10.1016/j.tetlet.2015.09.103
Dergi Adı: Tetrahedron Letters
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.6541-6545
Anahtar Kelimeler: Amino-benzothiophene, DFT calculations, Electrocyclization, Keteniminium salts
Boğaziçi Üniversitesi Adresli: Evet

Özet

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.