Investigation of cationic Claisen-type electrophilic rearrangements of amides

Herein we report an extension of the electrophilic rearrangement of amides to the preparation of α-prenyl-hydrocoumarins, indoles, isoquinolines and dihydro-isoquinolinones. An unusual competitive sulfonyl migration, uncovered upon attempted aza-Claisen rearrangement, is also described. [Display omi...

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Bibliographic Details
Published in:Tetrahedron 2015-09, Vol.71 (35), p.5994-6005
Main Authors: Padmanaban, Mohan, Carvalho, Luísa C.R., Petkova, Desislava, Lee, Ji-Woong, Santos, A. Sofia, Marques, M. Manuel B., Maulide, Nuno
Format: Article
Language:English
Subjects:
Amides
Hydrocoumarin
Isoquinolinone
oxa and aza-Claisen
Rearrangement
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Summary:Herein we report an extension of the electrophilic rearrangement of amides to the preparation of α-prenyl-hydrocoumarins, indoles, isoquinolines and dihydro-isoquinolinones. An unusual competitive sulfonyl migration, uncovered upon attempted aza-Claisen rearrangement, is also described. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.06.027