Investigation of cationic Claisen-type electrophilic rearrangements of amides

Mohan Padmanaban; Luisa C. R. Carvalho; Desislava Petkova; Ji-Woong Lee; A. Sofia Santos; Maria Manuel Martinho Sequeira Barata Marques; Nuno Maulide

doi:10.1016/j.tet.2015.06.027

Investigation of cationic Claisen-type electrophilic rearrangements of amides

Mohan Padmanaban, Luisa C. R. Carvalho, Desislava Petkova, Ji-Woong Lee, A. Sofia Santos, Maria Manuel Martinho Sequeira Barata Marques, Nuno Maulide

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

Herein we report an extension of the electrophilic rearrangement of amides to the preparation of a, prenyl-hydrocoumarins, indoles, isoquinolines and dihydro-isoquinolinones. An unusual competitive sulfonyl migration, uncovered upon attempted aza-Claisen rearrangement, is also described. (C) 2015 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	5994-6005
Number of pages	12
Journal	Tetrahedron
Volume	71
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2015.06.027
Publication status	Published - 2 Sept 2015

Keywords

oxa and aza-Claisen
Amides
Rearrangement
Hydrocoumarin
Isoquinolinone
ECHINULIN-TYPE COMPOUNDS
MODEL REACTION
3-ALKYL-1-ALLYLINDOLES
DERIVATIVES
BIOGENESIS
ACYLATION
INDOLES
OLEFINS
SALTS

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10.1016/j.tet.2015.06.027Licence: CC BY-NC-ND

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

abstract = "Herein we report an extension of the electrophilic rearrangement of amides to the preparation of a, prenyl-hydrocoumarins, indoles, isoquinolines and dihydro-isoquinolinones. An unusual competitive sulfonyl migration, uncovered upon attempted aza-Claisen rearrangement, is also described. (C) 2015 Elsevier Ltd. All rights reserved.",

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AU - Padmanaban, Mohan

AU - Carvalho, Luisa C. R.

AU - Petkova, Desislava

AU - Lee, Ji-Woong

AU - Sofia Santos, A.

AU - Marques, Maria Manuel Martinho Sequeira Barata

AU - Maulide, Nuno

N1 - Sem pdf conforme despacho. Fundacao para a Ciencia e Tecnologia (FCT) - (SFRH/BD/63407/2009; REQUIMTE:UID/QUI/50006/2013); Deutsche Forschungsgemeinschaft ( MA 4861/1-1 ; MA 4861/1-2)

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N2 - Herein we report an extension of the electrophilic rearrangement of amides to the preparation of a, prenyl-hydrocoumarins, indoles, isoquinolines and dihydro-isoquinolinones. An unusual competitive sulfonyl migration, uncovered upon attempted aza-Claisen rearrangement, is also described. (C) 2015 Elsevier Ltd. All rights reserved.

AB - Herein we report an extension of the electrophilic rearrangement of amides to the preparation of a, prenyl-hydrocoumarins, indoles, isoquinolines and dihydro-isoquinolinones. An unusual competitive sulfonyl migration, uncovered upon attempted aza-Claisen rearrangement, is also described. (C) 2015 Elsevier Ltd. All rights reserved.

KW - oxa and aza-Claisen

KW - Amides

KW - Rearrangement

KW - Hydrocoumarin

KW - Isoquinolinone

KW - ECHINULIN-TYPE COMPOUNDS

KW - MODEL REACTION

KW - 3-ALKYL-1-ALLYLINDOLES

KW - DERIVATIVES

KW - BIOGENESIS

KW - ACYLATION

KW - INDOLES

KW - OLEFINS

KW - SALTS

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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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