Investigations of fused 1,2,3-triazin-4-ones and related systems

Woodland, E.D., 1992. Investigations of fused 1,2,3-triazin-4-ones and related systems. PhD, Nottingham Trent University.

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This thesis describes work carried out on several chemical aspects of fused 1,2,3-triazin-4-ones.

In the first section several substituted 1,2,3-benzotriazinones were prepared with a view to observing their rate of deazoniation. It was envisaged that a kinetic analysis of this reaction would aid the elucidation of the nature of a hitherto controversial reaction intermediate. The rate constants obtained were used to construct Hammett plots and hence calculate the reaction constants. Several pieces of evidence were obtained that suggested the intermediate was of a diradical nature. Unfortunately, this could not be substantiated by Chemically Induced Dynamic Nuclear Polarisation spectroscopy.

The second section involved devising a new synthetic route for the preparation of 1,2,3-thieno- [3,4-d]triazinones since the one existing preparation gave polysubstituted products. A simple thienotriazinone was obtained which was used to study the reaction conditions required to cause its deazoniation. It was envisaged that for this reaction to occur, a potentially undesirable sulphur IV intermediate must be surmounted. As anticipated the thieno[3,4-d]triazinone did not deazoniate under the normal conditions. The synthetic route used to prepare the thieno[3,4-d]- triazinone also afforded an intermediate aminonitrile. An investigation into the versatility of this compound as a potential precursor to other fused heterocycles was undertaken. Several fused thienopyrimidines were obtained.

The final section of this work was dedicated to devising a synthetic route for the preparation of pyrrolo- and furanotriazinones. Unfortunately these compounds were not obtained due to difficulties of instability and excessive water solubility encountered in the synthesis, several useful intermediates were, however, successfully prepared.

Item Type: Thesis
Creators: Woodland, E.D.
Date: 1992
ISBN: 9781369324075
Divisions: Schools > School of Science and Technology
Record created by: Linda Sullivan
Date Added: 10 Nov 2020 15:48
Last Modified: 05 Oct 2023 09:50

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