Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs

Ciaran Paul Seath; James W. B. Fyfe; John J. Molloy; Allan J. B. Watson

doi:10.1055/s-0035-1562619

Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs

Ciaran Paul Seath, James W. B. Fyfe, John J. Molloy, Allan J. B. Watson

School of Chemistry

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

Abstract

The synthesis of functionalized oxindoles and benzofuranones via oxidation of 2-BMIDA indoles and benzofurans, respectively, is described. Interconversion of boron species (BMIDA→BF₃K) was necessary to enable oxidation and overcome boronic acid stability issues associated with a difficult BMIDA hydrolysis. Overall, a robust process was developed that allowed access to a small library of oxindole and benzofuranone products and facilitated the step-efficient synthesis of biologically-active compounds containing the oxindole pharmacophore.

Original language	English
Pages (from-to)	891-898
Journal	Synthesis
Volume	49
Issue number	4
Early online date	12 Aug 2016
DOIs	https://doi.org/10.1055/s-0035-1562619
Publication status	Published - Feb 2017

Keywords

Boron
Oxidation
Heterocycles
Lactams
Lactones
Functionalized oxindoles synthesis
Benzofuranones
Boronic acid stability
Oxindole pharmacophore

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10.1055/s-0035-1562619

https://strathprints.strath.ac.uk/id/eprint/57889

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title = "Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs",

abstract = "The synthesis of functionalized oxindoles and benzofuranones via oxidation of 2-BMIDA indoles and benzofurans, respectively, is described. Interconversion of boron species (BMIDA→BF3K) was necessary to enable oxidation and overcome boronic acid stability issues associated with a difficult BMIDA hydrolysis. Overall, a robust process was developed that allowed access to a small library of oxindole and benzofuranone products and facilitated the step-efficient synthesis of biologically-active compounds containing the oxindole pharmacophore.",

keywords = "Boron, Oxidation, Heterocycles, Lactams, Lactones, Functionalized oxindoles synthesis, Benzofuranones, Boronic acid stability, Oxindole pharmacophore",

author = "Seath, {Ciaran Paul} and Fyfe, {James W. B.} and Molloy, {John J.} and Watson, {Allan J. B.}",

year = "2017",

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language = "English",

volume = "49",

pages = "891--898",

journal = "Synthesis",

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T1 - Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs

AU - Seath, Ciaran Paul

AU - Fyfe, James W. B.

AU - Molloy, John J.

AU - Watson, Allan J. B.

PY - 2017/2

Y1 - 2017/2

N2 - The synthesis of functionalized oxindoles and benzofuranones via oxidation of 2-BMIDA indoles and benzofurans, respectively, is described. Interconversion of boron species (BMIDA→BF3K) was necessary to enable oxidation and overcome boronic acid stability issues associated with a difficult BMIDA hydrolysis. Overall, a robust process was developed that allowed access to a small library of oxindole and benzofuranone products and facilitated the step-efficient synthesis of biologically-active compounds containing the oxindole pharmacophore.

AB - The synthesis of functionalized oxindoles and benzofuranones via oxidation of 2-BMIDA indoles and benzofurans, respectively, is described. Interconversion of boron species (BMIDA→BF3K) was necessary to enable oxidation and overcome boronic acid stability issues associated with a difficult BMIDA hydrolysis. Overall, a robust process was developed that allowed access to a small library of oxindole and benzofuranone products and facilitated the step-efficient synthesis of biologically-active compounds containing the oxindole pharmacophore.

KW - Boron

KW - Oxidation

KW - Heterocycles

KW - Lactams

KW - Lactones

KW - Functionalized oxindoles synthesis

KW - Benzofuranones

KW - Boronic acid stability

KW - Oxindole pharmacophore

U2 - 10.1055/s-0035-1562619

DO - 10.1055/s-0035-1562619

M3 - Article

SN - 0039-7881

VL - 49

SP - 891

EP - 898

JO - Synthesis

JF - Synthesis

IS - 4

ER -

Synthesis of oxindoles and benozfuranones via oxidation of 2-heterocyclic BMIDAs

Abstract

Keywords

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