New developments in the 1-aza-Diels-Alder reaction : versatile routes to pyridines
In Chapter one a review of the l-aza-Diels-Alder reaction is presented. The hetero Diels-Alder reaction of l-aza-l,3-butadienes with both alkene and alkyne dienophiles has been shown to be an efficient and versatile method for the preparation of a large range of nitrogen-containing six-membered hete...
| Main Author: | |
|---|---|
| Format: | Thesis (University of Nottingham only) |
| Language: | English |
| Published: |
2008
|
| Online Access: | https://eprints.nottingham.ac.uk/13092/ |
| _version_ | 1848791649744846848 |
|---|---|
| author | Hurst, Timothy E. |
| author_facet | Hurst, Timothy E. |
| author_sort | Hurst, Timothy E. |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | In Chapter one a review of the l-aza-Diels-Alder reaction is presented. The hetero Diels-Alder reaction of l-aza-l,3-butadienes with both alkene and alkyne dienophiles has been shown to be an efficient and versatile method for the preparation of a large range of nitrogen-containing six-membered heterocycles. The use of electron-rich 1- azadienes in the normal electron-demand Diels-Alder reaction is primarily examined, followed by a brief look at the synthetic applications of the inverse electron-demand process.
In Chapter two the intermolecular hetero-Diels-Alder cyc1oadditions of 3-siloxy-1aza-1,3-butadienes with electron-deficient dienophiles is presented as an efficient route to tri- and tetra-substituted pyridine core of the thiopeptide antibiotic nosiheptide. A series of alpha, beta-unsaturated oximes and hydrazones were prepared and subsequently shown to participate readily in the hetero-Diels-Alder reaction with dimethyl acetylenedicarboxylate.
In Chapter three, the intramolecular Diels-Alder reaction is presented as a versatile method for the preparation of chromeno[ c ]pyridines. First a series of model systems was prepared and shown to undergo thermally induced intramolecular cyc1oaddition. This methodology was then utilised in the rapid preparation of the penta-substituted pyridine core of the anti tumour antibiotic streptonigrin.
Chapter four contains experimental procedures for all of the work detailed above. |
| first_indexed | 2025-11-14T18:31:52Z |
| format | Thesis (University of Nottingham only) |
| id | nottingham-13092 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T18:31:52Z |
| publishDate | 2008 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-130922025-02-28T11:23:06Z https://eprints.nottingham.ac.uk/13092/ New developments in the 1-aza-Diels-Alder reaction : versatile routes to pyridines Hurst, Timothy E. In Chapter one a review of the l-aza-Diels-Alder reaction is presented. The hetero Diels-Alder reaction of l-aza-l,3-butadienes with both alkene and alkyne dienophiles has been shown to be an efficient and versatile method for the preparation of a large range of nitrogen-containing six-membered heterocycles. The use of electron-rich 1- azadienes in the normal electron-demand Diels-Alder reaction is primarily examined, followed by a brief look at the synthetic applications of the inverse electron-demand process. In Chapter two the intermolecular hetero-Diels-Alder cyc1oadditions of 3-siloxy-1aza-1,3-butadienes with electron-deficient dienophiles is presented as an efficient route to tri- and tetra-substituted pyridine core of the thiopeptide antibiotic nosiheptide. A series of alpha, beta-unsaturated oximes and hydrazones were prepared and subsequently shown to participate readily in the hetero-Diels-Alder reaction with dimethyl acetylenedicarboxylate. In Chapter three, the intramolecular Diels-Alder reaction is presented as a versatile method for the preparation of chromeno[ c ]pyridines. First a series of model systems was prepared and shown to undergo thermally induced intramolecular cyc1oaddition. This methodology was then utilised in the rapid preparation of the penta-substituted pyridine core of the anti tumour antibiotic streptonigrin. Chapter four contains experimental procedures for all of the work detailed above. 2008-12-11 Thesis (University of Nottingham only) NonPeerReviewed application/pdf en arr https://eprints.nottingham.ac.uk/13092/1/493342.pdf Hurst, Timothy E. (2008) New developments in the 1-aza-Diels-Alder reaction : versatile routes to pyridines. PhD thesis, University of Nottingham. |
| spellingShingle | Hurst, Timothy E. New developments in the 1-aza-Diels-Alder reaction : versatile routes to pyridines |
| title | New developments in the 1-aza-Diels-Alder reaction : versatile routes to pyridines |
| title_full | New developments in the 1-aza-Diels-Alder reaction : versatile routes to pyridines |
| title_fullStr | New developments in the 1-aza-Diels-Alder reaction : versatile routes to pyridines |
| title_full_unstemmed | New developments in the 1-aza-Diels-Alder reaction : versatile routes to pyridines |
| title_short | New developments in the 1-aza-Diels-Alder reaction : versatile routes to pyridines |
| title_sort | new developments in the 1-aza-diels-alder reaction : versatile routes to pyridines |
| url | https://eprints.nottingham.ac.uk/13092/ |