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Durham University

Department of Chemistry

Publication details for Prof. Graham Sandford

Pattison, G., Sandford, G., Wilson, I., Yufit, D.S., Howard, J.A.K., Christopher, J.A. & Miller, D.D. (2017). Polysubstituted and ring-fused pyridazine systems from tetrafluoropyridazine. Tetrahedron 73(5): 437-454.

Author(s) from Durham

Abstract

Tetrafluoropyridazine 1 reacts with a range of oxygen-, nitrogen-, sulfur- and carbon-centred nucleophiles to give, in general, products 2 arising from substitution of fluorine para to ring nitrogen. Subsequent reaction of the trifluoropyridazine derivatives 2 gave a range of 4,5-di- and tri-substituted products 3 and 6. Related reactions of tetrafluoropyridazine 1 with difunctional nucleophiles gave [6,6]-, [5,6]- and [6,5,6]-polycyclic ring fused pyridazine scaffolds 4 and 9. Further functionalisation of scaffolds 4 by nucleophlic aromatic substitution processes involving displacement of fluorine atoms at activated sites ortho to ring nitrogen provide an indication of the synthetic possibilities offered using tetrafluoropyridazine as a starting material for the preparation of polysubstituted pyridazine and novel polyfunctional ring fused pyridazine systems with potential applications in the drug discovery arena.