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Studies on aminocyclobutenone rearrangements and a new C-H activation annulation reaction leading to N-heterocycles

Studies on aminocyclobutenone rearrangements and a new C-H activation annulation reaction leading to N-heterocycles
Studies on aminocyclobutenone rearrangements and a new C-H activation annulation reaction leading to N-heterocycles
This thesis describes study of aminocyclobutenone rearrangements. Thermal and photo rearrangements of cyclobutenones have become established as useful methods for the synthesis of quinones, naphthoquinones and furanones, some of which show useful biological activity. Though widely used, little is known about the behaviour of aminocyclobutenones. Herein, thermolyses and photolyses of aminocyclobutenones under continuous flow were studied in depth. DFT calculations were employed to bring greater understanding to our experimental results and identify new avenues for study.

In this work we also introduce a novel metal-free C-H activation and annulation reaction which could lead to N-heterocycles. Experimental work and DFT calculations were performed to understand the nature of this unusual reaction. We also delineated the regioselectivity and diastereoselectivity of this reaction.

A new rearrangement of cyclobutenones leading to 2-oxobut-3-enamides at low temperature has also been introduced. This new rearrangement offers a short and efficient route to synthesise highly substituted furans.
University of Southampton
Sun, Wei
495644d0-c7b5-4212-8160-8864f6c46953
Sun, Wei
495644d0-c7b5-4212-8160-8864f6c46953
Harrowven, David C.
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Sun, Wei (2017) Studies on aminocyclobutenone rearrangements and a new C-H activation annulation reaction leading to N-heterocycles. University of Southampton, Doctoral Thesis, 398pp.

Record type: Thesis (Doctoral)

Abstract

This thesis describes study of aminocyclobutenone rearrangements. Thermal and photo rearrangements of cyclobutenones have become established as useful methods for the synthesis of quinones, naphthoquinones and furanones, some of which show useful biological activity. Though widely used, little is known about the behaviour of aminocyclobutenones. Herein, thermolyses and photolyses of aminocyclobutenones under continuous flow were studied in depth. DFT calculations were employed to bring greater understanding to our experimental results and identify new avenues for study.

In this work we also introduce a novel metal-free C-H activation and annulation reaction which could lead to N-heterocycles. Experimental work and DFT calculations were performed to understand the nature of this unusual reaction. We also delineated the regioselectivity and diastereoselectivity of this reaction.

A new rearrangement of cyclobutenones leading to 2-oxobut-3-enamides at low temperature has also been introduced. This new rearrangement offers a short and efficient route to synthesise highly substituted furans.

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Published date: April 2017

Identifiers

Local EPrints ID: 413847
URI: http://eprints.soton.ac.uk/id/eprint/413847
PURE UUID: 2d65e49a-cc5c-4e0c-a3c6-bdd9fb80e85a
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 07 Sep 2017 16:33
Last modified: 29 Jun 2020 04:01

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Contributors

Author: Wei Sun
Thesis advisor: David C. Harrowven ORCID iD

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