| EPSRC Reference: |
GR/N38763/01 |
| Title: |
CHEMISTRY OF AMIDOCYCLOHEXADIENES: SYNTHESIS OF BENZEPRILS AND PYRROLO-PYRROLIDINES |
| Principal Investigator: |
Walton, Professor JC |
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| Department: |
Chemistry |
| Organisation: |
University of St Andrews |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
25 September 2000 |
Ends: |
24 September 2003 |
Value (£): |
53,196
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| EPSRC Research Topic Classifications: |
| Chemical Synthetic Methodology |
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| EPSRC Industrial Sector Classifications: |
| Pharmaceuticals and Biotechnology |
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Summary on Grant Application Form |
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Free radical mediated organic syntheses could be cleaner and more attractive for commercial applications, if efficient alternatives to toxic organotin hydrides could be found. This research aims to develop 1-amidocyclohexa-2,5-dienes as precursors to a range of aminoacyl radicals that can cyclise and yield lactams and related nitrogen heterocycles. Initial research focuses on optimising the methodology by use of derivatives containing oxime ether side chains. Cyclisation of aminoacyl radicals onto oxime ethers is expected to be efficient, even for small and medium (7-membered) rings. The process will then be used for the synthesis of benzepril, a potent inhibitor of angiotensin converting enzyme I, and related compounds. Trityl oxime ethers of the above type ring close to yield lactams in which the oxime functionality is restored. This provides the opportunity for a second synthetic stage in which the oxime is converted to an oxime ester that acts as the precursor to an iminyl radical. Ring closure of suitably functionalised iminyl-lactams to afford pyrrolo-pyrrolidinones and related novel heterocycles will be investigated.
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Key Findings |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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Potential use in non-academic contexts |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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Impacts |
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| Description |
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk |
| Summary |
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| Date Materialised |
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Sectors submitted by the Researcher |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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| Project URL: |
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| Further Information: |
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| Organisation Website: |
http://www.st-and.ac.uk |