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Novel Methods to Access Bioactive Molecules

Walsh, Anthony (2015) Novel Methods to Access Bioactive Molecules. Doctoral thesis, University of Huddersfield.

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This thesis is divided into two chapters detailing research on applying microwave methodology to access aminated nucleosides in significantly reduced time frames, and applying the Belluš-Claisen reaction to produce non-proteogenic dipeptides.
1. Amination of Nucleosides Using Microwave Methodology
2,2’-Anhydrouridine undergoes a ring opening reaction with aliphatic amines to give the corresponding aminated product. Under conventional heating reaction times are extremely lengthy, taking at least 3 to 4 days and up to a month in the case of very hindered amines. A modified procedure using microwave irradiation has proven to drastically reduce reaction time and has allowed access to novel nucleosides on gram scale.
2. Functionalised Amino Acids via the Belluš-Claisen Rearrangement
The Belluš-Claisen reaction is a [3,3] sigmatropic rearrangement of allylic amines, ethers and thioethers to give the corresponding amide, ester of thioester. A modified procedure of the Belluš-Claisen rearrangement was used to prepare functionalised dipeptides by reaction of a ketene prepared from N-phthaloylglycyl chloride in situ with allylic amino acid derivatives in the presence of a Lewis Acid and diisopropylethylamine. Rearrangments were successfully carried out using N,N-diallyl alanine and N-allyl proline. A range of N-allyl proline derivatives are demonstrated. However, attempts to repeat the reaction with structurally more complex amino acids did not result in successful reactions.

Item Type: Thesis (Doctoral)
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
Depositing User: Elizabeth Boulton
Date Deposited: 19 Jan 2016 15:26
Last Modified: 27 May 2016 00:48


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