Dr George W Weaver

Senior Lecturer in Organic Chemistry
BSc St Andrews, PhD Edin, CChem, MRSC
Telephone: 01509 222584
E-mail: G.W.Weaver@lboro.ac.uk

The main area of interest in this research group is heterocyclic chemistry.  We are interested in developing new methods for constructing heterocycles, in studying reaction mechanisms of ring forming reactions, and in studying the biological and physical properties of heterocyclic compounds.

Synthesis of Nitrogen Heterocycles

Work in this area is aimed at synthesising fused nitrogen heterocycles from highly functionalised small building blocks such as 1,1-diiodo-2,2-dintitroethene. We have used cycloaddition reactions to form substituted indolizines and pyrrrolo-fused isoqinolines. The scope and mechanism of such reactions in under investigation.

Synthesis of Fluorine Containing Heterocycles

This project area involves constructing fused nitrogen and sulfur heterocycles by aromatic nucleophilic substitution reactions of perfluorinated arenes. We have shown that lithiation of the bromophenyl tetrafluoropyrid-4-yl thioether leads to formation of a fused benzothiophene, whereas reaction of the corresponding oxyether proceeds by a Smiles-type rearrangement leading to the pyridyl phenol. Treatment of this compound with sodium hydride affords the fused benzofuran. The mechanisms of these types of reaction are under study and their application to the synthesis of new materials and  biologically active compounds is in progress.

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Polysulphide Natural Product Compounds

A number of natural products have recently been isolated from marine organisms and shown to contain unusual chains or rings of sulfur atoms.  Some of these compounds have anti-tumour or anti-fungal activity.  Our aim is to develop new methods for the synthesis of these types of compound as well as studying their mode of action. Only small amounts of these compounds can be isolated from natural sources, so synthesis will allow production of material for further study without damaging the marine environment.

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Publications

1. Radical Reactions with 3H-Quinazolin-4-ones: Synthesis of Deoxyvasicinone, Mackinazolinone, Luotonin A, Rutaecarpine and Tryptanthrin, W.R. Bowman, M.R.J. Elsegood, T. Stein and G.W. Weaver, Org. Biomol. Chem., 2007, 5, 103-113.
2. Unexpected ring Expansion of an Enantiopure Imidazoline Carbene Ligand, A. Sanchez Pelegri, M.R.J. Elsegood, V. McKee and G.W. Weaver, Org. Lett., 2006, 8, 3049-3051.
3. Synthesis of Substituted Indolizines and Pyrrolo[2,1-a]isoquinolines from 1,1-Diiodo-2,2-dinitroethylene. E. Boultadakis, B. Chung, M.R.J. Elsegood, G.W. Weaver. Synlett, 2002, 1547
4. Synthesis of 2-aryl-2H,4H-imidazo[4,5-d][1,2,3]triazoles from triethyl N-1-ethyl-2-methyl-4-nitro-1H-imidazol-5-yl phosphorimidate by reaction with aryl isocyanates. A. Taher, S. Eichenseher, A.M.Z. Slawin, G. Tennant and G.W. Weaver. J. Chem. Soc., Perkin Trans 1, 2002, 1968.
5. Aspects of Heterocyclisation Reactions Mediated by Nucleophilic Interaction of Aromatic Nitro Groups with ortho Heterocumulene Side Chains. K.J. Duffy, G. Tennant, C.J. Wallis and G.W. Weaver. ARKIVOC, 2002 (iii), 80-89.
6. Synthesis of 2-aryl-2H-indazoles by base catalysed reaction of 2-nitrobenzyl triphenylphosphonium bromide and aryl isocyanates. A. Taher, S. Ladwa, S. Thirumalai Rajan and G.W. Weaver. Tetrahedron Letters, 2000, 41, 9893.
7. Synthesis of 2-aryl-imidazo[4,5-d][1,2,3]triazoles from a 4-nitro-imidazol-5-yl phosphoramidate and aryl isocyanates. A. Taher, S. Eichenseher, and G.W. Weaver. Tetrahedron Letters, 2000, 41, 9889.
8. Reactions of an Imidazo[4,5-c]isoxazole-6-carboxylate with dimethyl acetylenedicarboxylate; formation of the first example of a [1,4]diazepino[2,3-c]isoxazole. A.Taher, A.M.Z. Slawin and G.W.Weaver. Tetrahedron Letters, 2000, 41, 9319.

Extended List of Publications