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New reactions of oxetanes
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Beasley, Benjamin O. (2013) New reactions of oxetanes. PhD thesis, University of Warwick.
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Official URL: http://webcat.warwick.ac.uk/record=b2698911~S1
Abstract
This thesis describes the synthesis and new reactions of oxetan-3-ones. Chapter 1
gives an introduction to oxetanes and includes discussion of methods for their
synthesis, their reactions, specifically those involving the use of oxetan-3-ones,
and their relevance in medicinal chemistry and natural products.
Chapter 2 begins with an introduction to multi-component reactions (MCRs) and
moves on to describe our efforts in incorporating oxetanes into structurally
diverse compounds using Passerini three-component reactions (P-3CRs) and Ugi
four-component reactions (U-4CRs). A range of 3,3-disubstituted oxetanes are
successfully made in 23-98% yield by reaction of oxetan-3-ones with various
carboxylic acids and isocyanides. The synthesis of chiral 2-substituted oxetan-3-
ones using the SAMP chiral auxiliary method is also demonstrated, specifically
oxetan-3-one is converted into 2-benzyloxetan-3-one in 51% overall yield and
74% ee in three steps.
Chapter 3 details our efforts towards the incorporation of the oxetane unit into
tetrahydro-β-carbolines using the Pictet-Spengler reaction. Several oxetan-3-ones
are demonstrated to take part in Pictet-Spengler reactions with tryptamine and
tryptophan ethyl ester derivatives. The chemistry is successfully extended in
azetidinones.
Item Type: | Thesis (PhD) |
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Subjects: | Q Science > QD Chemistry |
Library of Congress Subject Headings (LCSH): | Organic compounds -- Synthesis, Heterocyclic compounds -- Synthesis, Chemical reactions, Tryptamine, Lactams |
Official Date: | September 2013 |
Institution: | University of Warwick |
Theses Department: | Department of Chemistry |
Thesis Type: | PhD |
Publication Status: | Unpublished |
Supervisor(s)/Advisor: | Shipman, Michael |
Sponsors: | Engineering and Physical Sciences Research Council (EPSRC) |
Extent: | 169 leaves : illustrations. |
Language: | eng |
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