Date of Award

2008

Document type

Thesis

Degree Name

PhD (Doctor of Philosophy)

First Supervisor

Dr Mauro Adamo

Keywords

Chemistry, Pharmaceutical

Abstract

In the first part of this work we developed four novel methodologies for the generation of nitroso dienophile from commercially available hydroxamic acid I which is trapped with appropriate diene through a hetero-Diels-Alder (HDA) reaction (Scheme 1). These procedures afforded cycloadduct in good yields, employing reagents in a 1:1 ratio and only 5 mol.% catalyst loading. Remarkably, the crude reaction mixture showed the HDA adduct as the only compound present: this renders the reactions described herein as ideal for the development of tandem processes. Moreover, we demonstrated that these new methodologies can be applied to a large number of dienes.

In the second part we demonstrated the synthetic usefulness of styrylisoxazole IV which was used to access a number of compounds. Herein we describe the syntheses of aziridines V, N-Michael adducts VI, VII and VIII and S-Michael adducts IX which were obtained by reacting styrylisoxazole IV, with the corresponding nucleophile (Scheme 2).

We also report the one-pot preparation of S-Michael adducts IX from commercially available isoxazole X, an aromatic aldehyde XI and benzyl mercaptan XII (Scheme 3).

Creative Commons License

Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 3.0 License.

File Size

8.3MB

Comments

PhD thesis: a thesis submitted for the degree of Doctor of Philosophy to the Royal College of Surgeons in Ireland in 2008

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