Investigation of novel thermal cyclisation reactions

Avcil, Muhammet (2013) Investigation of novel thermal cyclisation reactions. Doctoral thesis (PhD), University of Sussex.

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Abstract

[For full abstract, with illustrations, see pdf file].

Part 1. Concise Synthesis of Highly Substituted Isoquinolin-1(2H)-ones via IMDA
The primary goal of this DPhil research project was to further investigate the mechanism of a novel thermally activated cyclisation reaction discovered within the Parsons’ research group.
Through the synthesis and cyclisation of the substituted pyrrole rings 2.38a-c we have
investigated the mechanism and increased the scope of the cyclisation reaction.

We have also developed a robust route to advanced intermediate 2.10 in the synthesis of
hymenialdisine 2.1.

Part 2. Investigation and Development of a Novel Cascade Reaction
The aim of this DPhil research project was to devise and execute a series of experiments to gain a better mechanistic understanding of the novel thermal cyclisation, discovered within the Parsons’ research group. To further investigate the mechanism and scope of the
cyclisation, the model system 2.1 was initially selected.

Through extensive modification and manipulation of the cyclisation precursor 2.1, we have
increased the scope of the cyclisation and postulated a reaction pathway. During these studies remarkable transformation of ketone 2.81 to alkyne 2.82 was also observed.
The repeatability of the above reactions was also investigated by synthesising various
analogues.

Item Type: Thesis (Doctoral)
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry > QD0241 Organic chemistry
Depositing User: Library Cataloguing
Date Deposited: 04 Dec 2013 07:50
Last Modified: 17 Sep 2015 13:12
URI: http://sro.sussex.ac.uk/id/eprint/47138

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