Reactions of tetrachloropyridazine with aliphatic nitrogen nucleophiles

Graham Pattison, Graham Sandford, Emma V.B. Wallace, Dmitry S. Yufit, Judith A.K. Howard, John A. Christopher, David D. Miller

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(Chemical Equation Presented) Nucleophilic aromatic substitution reactions of tetrachloropyridazine with a series of aliphatic primary and secondary amines led selectively to products arising from replacement of chlorine at the 4-position in all cases. The structures of the products were unambiguously confirmed by X-ray crystallography. Substitution occurs at the most activated site para to ring nitrogen, despite the possible steric hindrance to substitution by adjacent chlorine atoms, reflecting the activating influence of ring nitrogen meta to the site of attack. N,N′-Dimethylethylene diamine gave a mixture of [6,6] ring fused products following initial substitution at the 4-position.

Original languageEnglish
Pages (from-to)143-147
Number of pages5
JournalJournal of Heterocyclic Chemistry
Issue number1
Publication statusPublished - 1 Jan 2008

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    Pattison, G., Sandford, G., Wallace, E. V. B., Yufit, D. S., Howard, J. A. K., Christopher, J. A., & Miller, D. D. (2008). Reactions of tetrachloropyridazine with aliphatic nitrogen nucleophiles. Journal of Heterocyclic Chemistry, 45(1), 143-147.