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Title: Synthesis of 1,2-diamines using nitrogen-containing heterocyclic templates
Author: Iacobini, Greg
ISNI:       0000 0004 2732 7513
Awarding Body: University of Warwick
Current Institution: University of Warwick
Date of Award: 2012
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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.
Supervisor: Not available Sponsor: Engineering and Physical Sciences Research Council (EPSRC); Novartis (Firm)
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry ; QP Physiology