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

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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Identifiers

ORCID for David C. Harrowven: orcid.org/0000-0001-6730-3573

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