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Synthesis of 1,2-diamines using nitrogen-containing heterocyclic templates
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Iacobini, Greg (2012) Synthesis of 1,2-diamines using nitrogen-containing heterocyclic templates. PhD thesis, University of Warwick.
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Official URL: http://webcat.warwick.ac.uk/record=b2603418~S1
Abstract
This thesis describes the development of new methods for the synthesis of 1,2-
diamines. Chapter one reviews current methods for the synthesis of 1,2-
diamines, and their importance in chemistry. Chapter two highlights attempts to
synthesise 1,2-diamines using two nitrogen-containing heterocycles, namely 3-
phenyl-1,3,5-triazabicyclo[3.2.0]hept-6-ene-2,4-dione and imidazolin-2-one,
which both contain an endocyclic double bond. It includes the synthesis of a
novel 1,2-diazetine as well as the functionalisation of imidazolin-2-one via a
palladium-catalysed cross-coupling reaction with phenyl iodide. Subsequent
hydrogenation and hydrolysis was then utilised to afford 1-phenylethane-1,2-
diamine dihydrochloride. Chapter three describes the synthesis and
functionalisation of a range of 3-methylene-1,2-diazetidines that were
subsequently hydrogenated in an asymmetric fashion, with [Rh(NBD)2]BF4 and
ligand Mandyphos M004-1, to yield 1,2-diazetidines with up to 89% ee.
Reduction with LiDBB allowed for the synthesis of two carbamate-protected
1,2-diamines in three steps. The first examples of epoxidation, reaction with
tetracyanoethylene and 1,3-dipolar cycloadditions of 3-methylene-1,2-
diazetidines are reported. Chapter four details the experimental procedures and
characterisation data for the novel compounds produced.
| Item Type: | Thesis or Dissertation (PhD) | ||||
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| Subjects: | Q Science > QD Chemistry Q Science > QP Physiology |
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| Library of Congress Subject Headings (LCSH): | Heterocyclic compounds, Heterocyclic chemistry, Biosynthesis, Polyamines | ||||
| Official Date: | July 2012 | ||||
| Dates: |
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| 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| Publication Status: | Unpublished | ||||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); Novartis (Firm) | ||||
| Extent: | 180 leaves : illustrations, charts. | ||||
| Language: | eng |
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