Issue 71, 2024

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
06 Jan 2024
Accepted
29 Upu 2024
First published
02 Pha 2024

Chem. Commun., 2024,60, 9546-9549

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, 60, 9546 DOI: 10.1039/D4CC02760D

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