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Development of nova isocyanide based multicomponent reactions

Waller, RW; (2009) Development of nova isocyanide based multicomponent reactions. Doctoral thesis , UCL (University College London). Green open access

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Abstract

This thesis is divided into three parts. Part one presents an overview of isocyanide based multicomponent reactions, with a particular emphasis placed upon bifunctional substrates and novel nucleophilic partners for the Ugi reaction. Part two discusses the development of three-component reactions between N- alkyloxazolidines, isocyanides and carboxylic acids. This reaction is then further developed to allow it to be carried out in a four-component manner from an aminoethanol and carbonyl compound rather than an N-alkyloxazolidine. The use of M/-oxazolidines in a surprising three-component reaction with isocyanides and carboxylic acids is then discussed, with interesting mechanistic consequences. Novel nucleophilic partners for reactions with oxazolidines and isocyanides, rather than the ubiquitous carboxylic acids are then discussed, giving rise to novel structural frameworks. Bifunctional carbonyl-carboxylic acid substrates are then investigated as substrates for isocyanide based multicomponent reactions involving ethanolamines, leading to exciting new medium sized ring systems. Finally, hydroxy-carbonyl compounds are briefly discussed as substrates for isocyanide based multicomponent reactions. Part three describes the experimental procedures employed and results obtained.

Type: Thesis (Doctoral)
Title: Development of nova isocyanide based multicomponent reactions
Identifier: PQ ETD:593494
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Thesis digitised by ProQuest.
URI: http://discovery.ucl.ac.uk/id/eprint/1446164
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