Access to functionalized 3-amino-benzothiophenes using keteniminium intermediates

[Display omitted] 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...

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Bibliographic Details
Published inTetrahedron letters Vol. 56; no. 47; pp. 6541 - 6545
Main Authors Lumbroso, Alexandre, Behra, Julien, Kolleth, Amandine, Dakas, Pierre-Yves, Karadeniz, Ulfet, Catak, Saron, Sulzer-Mossé, Sarah, De Mesmaeker, Alain
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 25.11.2015
Elsevier
Subjects
Amino-benzothiophene
Chemistry
Chemistry, Organic
DFT calculations
Electrocyclization
Keteniminium salts
Physical Sciences
Science & Technology
Electrocyclization
Amino-benzothiophene
Keteniminium salts
DFT calculations
DENSITY FUNCTIONALS
MILD
EFFICIENT ACCESS
CYCLOBUTENIMINIUM SALTS
CYCLOBUTANONE
DERIVATIVES
PALLADIUM-CATALYZED AMINATION
AMIDES
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Summary:[Display omitted] 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.09.103