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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 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.
1359-7345
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.
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. (doi:10.1039/D1CC00393C).

Record type: Article

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.

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D1CC00393C - Accepted Manuscript
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Accepted/In Press date: 30 March 2021
e-pub ahead of print date: 30 March 2021

Identifiers

Local EPrints ID: 448294
URI: http://eprints.soton.ac.uk/id/eprint/448294
ISSN: 1359-7345
PURE UUID: 252dac75-e8e9-4545-aa65-681c7ee5ed66
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 19 Apr 2021 16:31
Last modified: 20 Apr 2021 01:37

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Contributors

Author: Morgan A. Manning
Author: Wei Sun
Author: Mark Light ORCID iD

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