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Title: The synthesis and reactions of deoxyvasicinone and analogous compounds
Author: Kinnear, K. I.
Awarding Body: Dundee College of Technology
Current Institution: Abertay University
Date of Award: 1986
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The synthesis of deoxyvasicinone and a number of its C-ring substituted pyrrolo[2,1-]quinazolin-9(1H)-one analogues was achieved. Modified 2-pyrrolidinones, the precursor molecules in many of the aforementioned syntheses, were prepared using standard techniques or via the reduction of nitrocarboxylic acid esters with reduced iron in acetic acid. The ability of deoxyvasicinone analogues to react at C-3 with electrophiles was demonstrated, the reactions yielding a range of modified pyrrolo[2,1-b]quinazolones. Mechanistic pathways to account for the products formed are included. A deuterium labelling experiment indicated that these reactions probably progress through the intermediacy of a pseudo-enamine. Deprotonation at the C-3 methylene group of 2,3-dihydro-pyrrolo[2,1-b]quinazolin-9(1H)-one and 2,3-dihydro-1,1-dimethylpyrrolo [2,1-b]quinazolin-9(1H)-one was achieved using lithium diisopropylamide and the lithiated species were used in situ for further synthetic transformations. Attempts to prepare novel tetracyclic systems utilising the sp2 nitrogen atom of the quinazolinone ring were unsuccessful. However, the tetracyclic spiroenone (A) was produced from deoxyvasicinone via an intermediate hydroxymethylene derivative. goodbreakmidinsertvskip 3.0cm endinsert
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Organic chemistry