Use this URL to cite or link to this record in EThOS: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.663030
Title: Studies on the scope of acid-catalysed cyclisation reactions of ortho-substituted nitroaromatic derivatives to N-hydroxy heterocycles and related compounds
Author: Tredgett, David Gordon
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2000
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Abstract:
The subject matter of this thesis is concerned with investigations on the novel acid-catalyst cyclisation reactions of ortho- substituted nitroaromatic derivatives to N-oxygenated quinolinones and related heterocycles. The description of the results obtained in these studies is preceded in Chapter 1 by a survey of the known acid-catalysed cyclisation reactions of ortho-substituted nitroaromatic derivatives to N-oxygenated heterocycles and the potential biological properties of such N-oxygenated heterocyclic derivatives. Chapter 2 describes investigations on the synthesis of N-hydroxyquinolinone derivatives by the acid-catalysed cyclisation reactions of ortho- substituted nitrobenzene derivatives. In particular these studies were concerned with substituent effects para to the ortho- side- chain in the nitrobenzene derivatives in respect of the efficiency of their cyclisation to N-hydroxyquinolinone derivatives in the presence of hydrogen chloride. Subsequent studies on the reactivity of the N-hydroxyquinolinone derivatives obtained are also reported in this Chapter. Investigations were also carried out on the Lewis acid catalysed cyclisation reactions of trans 2-benzoyl-3-(2-nitrophenyl)oxirane derivatives to novel 2,1-benzisoxazolone derivatives. Chapter 3 describes the efficient synthesis of novel N-hydroxybenzoquinolinone derivatives by the hydrogen chloride catalysed cyclisation reactions of 2-nitronaphthylidene derivatives as well as investigations of the reactivity of the N-hydroxy heterocycles so produced. Studies seeking to extend this work to the synthesis of N-hydroxythienopyridinones and N-hydroxyimidazopyridinones by the acid-catalysed cyclisation reactions of the corresponding nitrothienylidene and nitroimidazolylidene derivatives are also reported. Also described in this Chapter are studies on the hydrogen chloride and Lewis acid catalysed cyclisation reactions of 2-nitronaphthyloxirane, 2-nitrothienyloxirane and 5-nitroimidazolyloxirane derivatives, in the case of the Lewis acid promoted processes to afford naphthisoxazolone, thienoisoxazolone and imidazoisoxazolone derivatives.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID: uk.bl.ethos.663030  DOI: Not available
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