A photochemical ring expansion of 6- to 8-membered nitrogen heterocycles by [1,3]-sigmatropic rearrangement
A photochemical ring expansion of 6- to 8-membered nitrogen heterocycles by [1,3]-sigmatropic rearrangement
A new route to azocines and benzoazocines from furopyridinones is described through a photochemically induced [1,3]-sigmatropic rearrangement. The method gives access to these 8-membered nitrogen heterocycles from dimethyl squarate in four stages and with excellent atom economy by sequencing thermal and photochemical ring expansion steps under continuous flow.
4556-4559
Manning, Morgan A.
9e0de846-7301-4fdf-9a4d-60ef681e2974
Sun, Wei
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Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
7 May 2021
Manning, Morgan A.
9e0de846-7301-4fdf-9a4d-60ef681e2974
Sun, Wei
bca29e03-90fc-4684-875e-61d35f1b5cba
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Manning, Morgan A., Sun, Wei, Light, Mark and Harrowven, David C.
(2021)
A photochemical ring expansion of 6- to 8-membered nitrogen heterocycles by [1,3]-sigmatropic rearrangement.
ChemComm, 57 (37), .
(doi:10.1039/D1CC00393C).
Abstract
A new route to azocines and benzoazocines from furopyridinones is described through a photochemically induced [1,3]-sigmatropic rearrangement. The method gives access to these 8-membered nitrogen heterocycles from dimethyl squarate in four stages and with excellent atom economy by sequencing thermal and photochemical ring expansion steps under continuous flow.
Text
D1CC00393C
- Accepted Manuscript
More information
Accepted/In Press date: 30 March 2021
e-pub ahead of print date: 30 March 2021
Published date: 7 May 2021
Additional Information:
Funding Information:
We gratefully acknowledge financial support from the European Regional Development Fund [ERDF Interreg Va programme (Project 121)] and EPSRC [EP/P013341/1, EP/L003325/1 and EP/ K039466/1].
Publisher Copyright:
© The Royal Society of Chemistry.
Identifiers
Local EPrints ID: 448294
URI: http://eprints.soton.ac.uk/id/eprint/448294
ISSN: 1359-7345
PURE UUID: 252dac75-e8e9-4545-aa65-681c7ee5ed66
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Date deposited: 19 Apr 2021 16:31
Last modified: 17 Mar 2024 02:48
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Contributors
Author:
Morgan A. Manning
Author:
Wei Sun
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