Investigation of cationic Claisen-type electrophilic rearrangements of amides

Mohan Padmanaban; Luísa C.R. Carvalho; Desislava Petkova; Jiwoong Lee; A. Sofia Santos; M. Manuel B. Marques; Nuno Maulide

doi:10.1016/j.tet.2015.06.027

Investigation of cationic Claisen-type electrophilic rearrangements of amides

Mohan Padmanaban, Luísa C.R. Carvalho, Desislava Petkova, Jiwoong Lee, A. Sofia Santos, M. Manuel B. Marques, Nuno Maulide

10 Citations (Scopus)

Abstract

Abstract 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.

Original language	English
Journal	Tetrahedron
Volume	71
Issue number	35
Pages (from-to)	5994-6005
Number of pages	12
ISSN	0040-4020
DOIs	https://doi.org/10.1016/j.tet.2015.06.027
Publication status	Published - 25 Jul 2015
Externally published	Yes

Keywords

Amides
Hydrocoumarin
Isoquinolinone
Rearrangement
oxa and aza-Claisen

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10.1016/j.tet.2015.06.027

Cite this

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title = "Investigation of cationic Claisen-type electrophilic rearrangements of amides",

abstract = "Abstract 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.",

keywords = "Amides, Hydrocoumarin, Isoquinolinone, Rearrangement, oxa and aza-Claisen",

author = "Mohan Padmanaban and Carvalho, {Lu{\'i}sa C.R.} and Desislava Petkova and Jiwoong Lee and Santos, {A. Sofia} and Marques, {M. Manuel B.} and Nuno Maulide",

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doi = "10.1016/j.tet.2015.06.027",

language = "English",

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TY - JOUR

T1 - Investigation of cationic Claisen-type electrophilic rearrangements of amides

AU - Padmanaban, Mohan

AU - Carvalho, Luísa C.R.

AU - Petkova, Desislava

AU - Lee, Jiwoong

AU - Santos, A. Sofia

AU - Marques, M. Manuel B.

AU - Maulide, Nuno

PY - 2015/7/25

Y1 - 2015/7/25

N2 - Abstract 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.

AB - Abstract 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.

KW - Amides

KW - Hydrocoumarin

KW - Isoquinolinone

KW - Rearrangement

KW - oxa and aza-Claisen

U2 - 10.1016/j.tet.2015.06.027

DO - 10.1016/j.tet.2015.06.027

M3 - Journal article

SN - 0040-4020

VL - 71

SP - 5994

EP - 6005

JO - Tetrahedron

JF - Tetrahedron

IS - 35

ER -

Investigation of cationic Claisen-type electrophilic rearrangements of amides

Abstract

Keywords

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