Synthesis of polysubstituted pyridazines via Cu-mediated C(sp3)-C(sp3) coupling/annulation of saturated ketones with acylhydrazones

Abstract

Pyridazine is a significant skeleton that widely exists in drugs and bioactive molecules. We herein describe expeditious approaches to access polysubstituted pyridazines from readily accessible unactivated ketones and acylhydrazones via Cu-promoted C(sp3)-C(sp3) coupling/cyclization sequences in a single-step fashion. Notably, the disparate 3,4,6-trisubstituted pyridazines and 3,5-disubstituted pyridazines could be obtained by tailoring the ketone’s structure and reaction conditions. These transformations feature good functional group compatibility, excellent step-economy, and chemoselectivity. The potential synthetic utility of these conversions is illustrated by scale-up reactions and late-stage derivatizations of the as-prepared pyridazine products.

Supplementary files

Article information

Article type
Communication
Submitted
06 Jun 2024
Accepted
29 Jul 2024
First published
02 Aug 2024

Chem. Commun., 2024, Accepted Manuscript

Synthesis of polysubstituted pyridazines via Cu-mediated C(sp3)-C(sp3) coupling/annulation of saturated ketones with acylhydrazones

H. Zhou, Z. Li, J. Chen, S. Zhou, X. Wang, L. Zhang, J. Chen and N. Lv, Chem. Commun., 2024, Accepted Manuscript , DOI: 10.1039/D4CC02760D

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