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.

Metadata

Item Type:	Article
Authors/Creators:	Inprung, Nantachai Whitwood, Adrian C. Taylor, Richard J.K. https://orcid.org/0000-0002-5880-2490 James, Michael J. https://orcid.org/0000-0003-2591-0046 Unsworth, William P. https://orcid.org/0000-0002-9169-5156
Copyright, Publisher and Additional Information:	Funding Information: The authors would like to thank the Development and Promotion of Science and Technology Talents Project (DPST), Royal Thai Government. (N.I. EP/N035119/1), the University of York, and the University of Manchester for financial support. We would also like to thank Prof. Victor Chechik for helpful discussions. Publisher Copyright: © 2023 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH.
Keywords:	cascade,dearomatisation,radical,ring expansion,spirocyclisation
Dates:	Published (online): 27 September 2023 Accepted: 14 August 2023
Institution:	The University of York
Academic Units:	The University of York > Faculty of Sciences (York) > Chemistry (York)
Depositing User:	Pure (York)
Date Deposited:	06 Oct 2023 08:30
Last Modified:	26 Nov 2024 00:58
Published Version:	https://doi.org/10.1002/ejoc.202300603
Status:	Published online
Refereed:	Yes
Identification Number:	10.1002/ejoc.202300603
Related URLs:	http://www.scopus.com/inward/record.url?...
Open Archives Initiative ID (OAI ID):	oai:eprints.whiterose.ac.uk:204013

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Radical Dearomatising Spirocyclisation of Benzisoxazole-Tethered Ynones

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