Radical Dearomatising Spirocyclisation of Benzisoxazole‐Tethered Ynones

Nantachai Inprung; Adrian C. Whitwood; Richard J. K. Taylor; Michael J. James; William P. Unsworth

doi:10.1002/ejoc.202300603

Radical Dearomatising Spirocyclisation of Benzisoxazole‐Tethered Ynones

Nantachai Inprung, Adrian C. Whitwood, Richard J. K. Taylor, Michael J. James^*, William P. Unsworth^*

^*Corresponding author for this work

Organic Chemistry Group

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

Abstract

The dearomative spirocyclisation of benzisoxazoles through a radical chain mechanism is described. Densely functionalised spirocycles were prepared in high yields by reacting benzisoxazole-tethered ynones with aryl thiols in 1,2-dichloroethane (DCE) at 60 °C. The identification of stabilising three-electron interactions was key to the development of this new radical cascade reaction. The obtained spirocyclic products were converted into other spirocyclic scaffolds through a two-step hydrogenolysis-cyclisation sequence.

Original language	English
Number of pages	5
Journal	European Journal of Organic Chemistry
Early online date	27 Sept 2023
DOIs	https://doi.org/10.1002/ejoc.202300603
Publication status	Published - 2 Nov 2023

Keywords

cascade
dearomatisation
radical
ring expansion
spirocyclisation

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10.1002/ejoc.202300603Licence: CC BY

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title = "Radical Dearomatising Spirocyclisation of Benzisoxazole‐Tethered Ynones",

abstract = "The dearomative spirocyclisation of benzisoxazoles through a radical chain mechanism is described. Densely functionalised spirocycles were prepared in high yields by reacting benzisoxazole-tethered ynones with aryl thiols in 1,2-dichloroethane (DCE) at 60 °C. The identification of stabilising three-electron interactions was key to the development of this new radical cascade reaction. The obtained spirocyclic products were converted into other spirocyclic scaffolds through a two-step hydrogenolysis-cyclisation sequence.",

keywords = "cascade, dearomatisation, radical, ring expansion, spirocyclisation",

author = "Nantachai Inprung and Whitwood, {Adrian C.} and Taylor, {Richard J. K.} and James, {Michael J.} and Unsworth, {William P.}",

year = "2023",

month = nov,

day = "2",

doi = "10.1002/ejoc.202300603",

language = "English",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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TY - JOUR

T1 - Radical Dearomatising Spirocyclisation of Benzisoxazole‐Tethered Ynones

AU - Inprung, Nantachai

AU - Whitwood, Adrian C.

AU - Taylor, Richard J. K.

AU - James, Michael J.

AU - Unsworth, William P.

PY - 2023/11/2

Y1 - 2023/11/2

N2 - The dearomative spirocyclisation of benzisoxazoles through a radical chain mechanism is described. Densely functionalised spirocycles were prepared in high yields by reacting benzisoxazole-tethered ynones with aryl thiols in 1,2-dichloroethane (DCE) at 60 °C. The identification of stabilising three-electron interactions was key to the development of this new radical cascade reaction. The obtained spirocyclic products were converted into other spirocyclic scaffolds through a two-step hydrogenolysis-cyclisation sequence.

AB - The dearomative spirocyclisation of benzisoxazoles through a radical chain mechanism is described. Densely functionalised spirocycles were prepared in high yields by reacting benzisoxazole-tethered ynones with aryl thiols in 1,2-dichloroethane (DCE) at 60 °C. The identification of stabilising three-electron interactions was key to the development of this new radical cascade reaction. The obtained spirocyclic products were converted into other spirocyclic scaffolds through a two-step hydrogenolysis-cyclisation sequence.

KW - cascade

KW - dearomatisation

KW - radical

KW - ring expansion

KW - spirocyclisation

UR - https://doi.org/10.1002/ejoc.202300603

U2 - 10.1002/ejoc.202300603

DO - 10.1002/ejoc.202300603

M3 - Article

SN - 1434-193X

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -

Radical Dearomatising Spirocyclisation of Benzisoxazole‐Tethered Ynones

Abstract

Keywords

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