Formation of a tetracyclic isoquinoline derivative by rearrangement of a [(bromophenyl)butyryl]oxazolidinone

John Christopher Walton; M D Roydhouse

doi:10.1002/ejoc.20060918

Formation of a tetracyclic isoquinoline derivative by rearrangement of a [(bromophenyl)butyryl]oxazolidinone

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Abstract

Treatment of 3-[4-(2-bromophenyl)-2-phenylbutyryl]-4,4-dimethyloxazohdin-2-one with LDA in THF launched a domino rearrangement sequence ending in the assembly of a tetracyclic cyclopentaoxazolo[3,2-b]isoquinolin-6-one derivative. Two mechanisms involving an S(RN)1-type process were proposed. EPR spectroscopic and C-13-labelling experiments suggested that both were operative. (C) Wiley-VCH Verlag GmbH & Co.

Original language	English
Pages (from-to)	1059-1063
Number of pages	5
Journal	European Journal of Organic Chemistry
DOIs	https://doi.org/10.1002/ejoc.20060918
Publication status	Published - Feb 2007

Keywords

rearrangement
cyclisation
heterocycles
radical ions
EPR spectroscopy
NUCLEOPHILIC-SUBSTITUTION
CHLORANILINES
CYCLIZATIONS
DIANIONS

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title = "Formation of a tetracyclic isoquinoline derivative by rearrangement of a [(bromophenyl)butyryl]oxazolidinone",

abstract = "Treatment of 3-[4-(2-bromophenyl)-2-phenylbutyryl]-4,4-dimethyloxazohdin-2-one with LDA in THF launched a domino rearrangement sequence ending in the assembly of a tetracyclic cyclopentaoxazolo[3,2-b]isoquinolin-6-one derivative. Two mechanisms involving an S(RN)1-type process were proposed. EPR spectroscopic and C-13-labelling experiments suggested that both were operative. (C) Wiley-VCH Verlag GmbH \& Co.",

keywords = "rearrangement, cyclisation, heterocycles, radical ions, EPR spectroscopy, NUCLEOPHILIC-SUBSTITUTION, CHLORANILINES, CYCLIZATIONS, DIANIONS",

author = "Walton, \{John Christopher\} and Roydhouse, \{M D\}",

year = "2007",

month = feb,

doi = "10.1002/ejoc.20060918",

language = "English",

pages = "1059--1063",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Weinheim",

}

TY - JOUR

T1 - Formation of a tetracyclic isoquinoline derivative by rearrangement of a [(bromophenyl)butyryl]oxazolidinone

AU - Walton, John Christopher

AU - Roydhouse, M D

PY - 2007/2

Y1 - 2007/2

N2 - Treatment of 3-[4-(2-bromophenyl)-2-phenylbutyryl]-4,4-dimethyloxazohdin-2-one with LDA in THF launched a domino rearrangement sequence ending in the assembly of a tetracyclic cyclopentaoxazolo[3,2-b]isoquinolin-6-one derivative. Two mechanisms involving an S(RN)1-type process were proposed. EPR spectroscopic and C-13-labelling experiments suggested that both were operative. (C) Wiley-VCH Verlag GmbH & Co.

AB - Treatment of 3-[4-(2-bromophenyl)-2-phenylbutyryl]-4,4-dimethyloxazohdin-2-one with LDA in THF launched a domino rearrangement sequence ending in the assembly of a tetracyclic cyclopentaoxazolo[3,2-b]isoquinolin-6-one derivative. Two mechanisms involving an S(RN)1-type process were proposed. EPR spectroscopic and C-13-labelling experiments suggested that both were operative. (C) Wiley-VCH Verlag GmbH & Co.

KW - rearrangement

KW - cyclisation

KW - heterocycles

KW - radical ions

KW - EPR spectroscopy

KW - NUCLEOPHILIC-SUBSTITUTION

KW - CHLORANILINES

KW - CYCLIZATIONS

KW - DIANIONS

UR - https://www.scopus.com/pages/publications/34250626098

U2 - 10.1002/ejoc.20060918

DO - 10.1002/ejoc.20060918

M3 - Article

SN - 1434-193X

SP - 1059

EP - 1063

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -