Novel one-pot multi-reaction methods for the synthesis of carbocyclic and heterocyclic compounds

Faggyas, Réka Julianna (2019) Novel one-pot multi-reaction methods for the synthesis of carbocyclic and heterocyclic compounds. PhD thesis, University of Glasgow.

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Abstract

The first section describes the development of an asymmetric one-pot synthesis of 1-alkylindan-1-ols involving an enantioselective allylboration of 2’-bromoaryl alkyl ketones followed by an intramolecular Mizoroki-Heck cyclisation. The synthetic utility of the chiral 1-alkylindan-1-ol scaffold was demonstrated using the ozonolysis product indanone in diastereoselective reductive reactions.

The second section describes the development of a rapid, one-pot tandem diazotisation and Heck-Matsuda reaction for the synthesis of methyl (E)-cinnamates via stable aryl diazonium tosylate salts. This process was then altered to allow the one-pot multistep synthesis of 3,4-dihydroquinolin-2-ones. This methodology was used for the total synthesis of a sodium channel modulator.

The third section describes a one-pot diazotisation-intramolecular cyclisation process for the synthesis of 1H-benzotriazoles and the regioselective preparation of N1-substituted benzotriazoles, including a series of biologically active compounds.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: One-pot reactions, Multistep reactions, Tandem catalysis, Transition metal catalysis, Palladium catalysis, Indanols, Diazotisation, Quinolones, Benzotriazoles.
Subjects: Q Science > QD Chemistry
Colleges/Schools: College of Science and Engineering > School of Chemistry
Supervisor's Name: Sutherland, Dr Andrew
Date of Award: 2019
Depositing User: Miss Réka Faggyas
Unique ID: glathesis:2019-75136
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 30 Oct 2019 11:11
Last Modified: 30 Oct 2019 11:35
Thesis DOI: 10.5525/gla.thesis.75136
URI: http://theses.gla.ac.uk/id/eprint/75136
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