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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

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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)
Subjects: Q Science > QD Chemistry
Q Science > QP Physiology
Library of Congress Subject Headings (LCSH): Heterocyclic compounds, Heterocyclic chemistry, Biosynthesis, Polyamines
Official Date: July 2012
Dates:
DateEvent
July 2012Submitted
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Publication Status: Unpublished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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