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Electrophilic substitution of five-membered heterocyclic compounds : electrophilic substitution of the phenyl-1,2,4-triazoles : synthetic studies of some [beta]-triketones

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Blackman, Adrian John (1964) Electrophilic substitution of five-membered heterocyclic compounds : electrophilic substitution of the phenyl-1,2,4-triazoles : synthetic studies of some [beta]-triketones. Unspecified thesis, University of Tasmania.

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Abstract

The action of most common oxidising agents on 1,2,4-
triazoline -3 -thione leads to ready cleavage of the C-S bond
to yield 1,2,4-triazole. Prior to this work no 1,2,4-triazole -
3 -sulphonic acids had been reported. Several oxidative methods
have been developed which yield 1,2,4-triazole -3 -sulphonic acid;
of these chlorine oxidation is the most convenient.
A literature survey of the oxidation of heterocyclic thiols
and thiones has been made. Syntheses of substituted 1,2,4-
triazoline -3 -thiones have been reviewed. Thirty monosubstituted 1,2,4-triazoline -3 -thiones as well
as several disubstituted 1 1 2,4-triazoline-3-thiones, 1,2 1 4-
triazolidine -3,5 -dithiones, di -(1,2,4-triazoline -3-thiones),
and fused ring 1,2,4-triazoline -3 -thiones have been prepared.
Chlorine oxidation of all these compounds has been investigated.
In most cases the corresponding sulphonyl chlorides were formed
initially, and these were then hydrolysed to the sulphonic acid
or converted to the sulphonamide. Approximately thirty acids
and fifteen amides were prepared in this way. With certain
2-substituted 1,2,4-triazoline -3 -thiones no sulphonyl chlorides
nor sulphonic acids could be isolated, while with certain
substituents in the 4-position the intermediate sulphonyl
chlorides were formed but could not be converted into the
corresponding sulphonic acids. Bromine oxidation of several monosubstituted 1,2,4-
triazoline -3 -thiones also yielded the corresponding sulphonic
acids though yields were very poor for the parent thione.

Item Type: Thesis (Unspecified)
Keywords: Heterocyclic compounds, Triazoles, Ketones
Copyright Holders: The Author
Additional Information:

In title, the Greek symbol for "beta" is used. Thesis (B.Sc.(Hons.))--University of Tasmania, 1965. Includes bibliographical references

Date Deposited: 25 Nov 2014 00:53
Last Modified: 11 Mar 2016 05:56
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