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Studies on the generation of chemical diversity using hetero Diels Alder reactions and polyfunctional scaffolds
Bruschi, Simone
<p>In the first part of this work we developed four novel methodologies for the generation of nitroso dienophile from commercially available hydroxamic acid <strong>I</strong> which is trapped with appropriate diene through a hetero-Diels-Alder (HDA) reaction (<strong>Scheme 1</strong>). 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.</p> <p>In the second part we demonstrated the synthetic usefulness of styrylisoxazole<strong> IV</strong> which was used to access a number of compounds. Herein we describe the syntheses of aziridines <strong>V</strong>, <em>N</em>-Michael adducts<strong> VI</strong>, <strong>VII</strong> and <strong>VIII</strong> and <em>S</em>-Michael adducts<strong> IX</strong> which were obtained by reacting styrylisoxazole<strong> IV</strong>, with the corresponding nucleophile (<strong>Scheme 2</strong>).</p> <p>We also report the one-pot preparation of <em>S</em>-Michael adducts<strong> IX</strong> from commercially available isoxazole <strong>X</strong>, an aromatic aldehyde <strong>XI</strong> and benzyl mercaptan <strong>XII</strong> (<strong>Scheme 3</strong>).</p> <p>PhD thesis: a thesis submitted for the degree of Doctor of Philosophy to the Royal College of Surgeons in Ireland in 2008</p>
Keyword(s): Chemistry; Pharmaceutical; Medicine and Health Sciences
Publication Date:
2008
Type: Doctoral thesis
Peer-Reviewed: No
Institution: Royal College of Surgeons in Ireland
Citation(s): Bruschi S. Studies on the generation of chemical diversity using hetero Diels Alder reactions and polyfunctional scaffolds [PhD Thesis]. Dublin: Royal College of Surgeons in Ireland; 2008.
Supervisor(s): Dr Mauro Adamo
Related Link(s): http://epubs.rcsi.ie/phdtheses/88
First Indexed: 2015-07-31 15:37:11 Last Updated: 2018-02-13 07:19:08