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

Research output: Contribution to journal › Journal article › Research › peer-review

13 Citations (Scopus)

Abstract

Abstract Herein we report an extension of the electrophilic rearrangement of amides to the preparation of ??-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 - 2015
Externally published	Yes

Keywords

Amides
Hydrocoumarin
Isoquinolinone
Rearrangement
oxa and aza-Claisen

Access to Document

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 ??-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",

year = "2015",

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

language = "English",

volume = "71",

pages = "5994--6005",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Pergamon Press",

number = "35",

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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

Y1 - 2015

N2 - Abstract Herein we report an extension of the electrophilic rearrangement of amides to the preparation of ??-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 ??-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

VL - 71

SP - 5994

EP - 6005

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 35

ER -