Facile Synthesis of 3,6‐Diaminopyridazine

Abstract

An efficient two‐step synthesis of 3,6‐diaminopyridazine from 3,6‐dichloropyridazine is reported. In this synthetic procedure, 4‐methoxybenzylamine was used as a nitrogen source to substitute the chloro groups of 3,6‐dichloropyridazine to form N,N′‐bis‐(4‐methoxybenzyl)‐pyridazine‐3,6‐diamine. The 4‐methoxybenzyl groups were then removed by treatment with hydrochloric acid to provide the target 3,6‐diaminopyridazine with an overall yield of 78%.

Keywords:

• heterocycles
• nucleophilic aromatic substitutions
• pyridazines
• supramolecular chemistry

Acknowledgments

The authors are grateful to Concordia University and Queen's University, Natural Sciences and Engineering Research Council [Canada] (NSERC), Ministry of Research and Innovation [Ontario] (MRI), Le Fonds québécois de la recherche sur la nature et les technologies (FQRNT), and Canada Foundation for Innovation (CFI) for funding, to S. Zimmerman for valuable discussions, and to Michael J. Krische for useful suggestions and proofreading the manuscript.