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Title: Investigations of new synthetic routes to cinnoline and fused cinnoline derivatives
Author: Scobie, Martin
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 1992
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The subject matter of this thesis is concerned with the investigation of new synthetic routes to cinnoline and fused cinnoline derivatives. A description of the results obtained in these studies is preceded in Chapter 1 by a survey of literature methods for the synthesis of cinnoline derivatives. Chapter 2 describes an investigation into the use of 2-nitroaroylformimidates as intermediates in the synthesis of 3,4-substituted cinnoline derivatives and in particular 2-amino-3-(2-nitroaryl)quinoxalines. The base-catalysed cyclisation of the latter compounds, to afford quinoxalino[2,3-c]cinnoline N-oxides is also reported and the scope of this method investigated. Chapter 3 describes the synthesis of 3-amino-5-hydroxy-4-(2-nitroaryl)-2H-pyrazole derivatives and their base-catalysed cyclisation to give 1-hydroxy-3H-pyrazolo[3,4-c]cinnoline N-oxides. The influence of substituent effects on the scope of this cyclisation is also studied. Furthermore the oxidative ring-scission of the resulting hydroxypyrazolo[3,4-c]cinnoline derivatives to afford cinnoline-4-carboxylic acid 1-N-oxides is also reported. Chapter 4 deals with studies on the synthesis and cyclisation of 3-amino-4-(2-nitroaryl)isoxazol-5(2H)-ones. Base-induced cyclisation of the isoxazolone derivatives afforded isoxazolo[3,4-c]cinnolinones which were converted to 3-aminocinnoline-4-carboxylic acid N-oxides by their reaction with hydrazine.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available