G. Pattison
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.
Authors
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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Copyright Statement
© 2016 This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
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