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Polysubstituted and ring-fused pyridazine systems from tetrafluoropyridazine

Pattison, G.; Sandford, G.; Wilson, I.; Yufit, D.S.; Howard, J.A.K.; Christopher, J.A.; Miller, D.D.

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Authors

G. Pattison

G. Sandford

I. Wilson

D.S. Yufit

J.A.K. Howard

J.A. Christopher

D.D. Miller



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.

Citation

Pattison, G., Sandford, G., Wilson, I., Yufit, D., Howard, J., Christopher, J., & Miller, D. (2017). Polysubstituted and ring-fused pyridazine systems from tetrafluoropyridazine. Tetrahedron, 73(5), 437-454. https://doi.org/10.1016/j.tet.2016.12.006

Journal Article Type Article
Acceptance Date Dec 6, 2016
Online Publication Date Dec 9, 2016
Publication Date Feb 2, 2017
Deposit Date Dec 21, 2016
Publicly Available Date Dec 9, 2017
Journal Tetrahedron
Print ISSN 0040-4020
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 73
Issue 5
Pages 437-454
DOI https://doi.org/10.1016/j.tet.2016.12.006

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