Synthesis of (hetero)arylated pyridazin-3(2H)-ones via Negishi reaction involving zincated pyridazin-3(2H)-ones

Tom Verhelst; Zuming Liu; Jens Maes; Bert U W Maes

doi:10.1021/jo201587j

Synthesis of (hetero)arylated pyridazin-3(2H)-ones via Negishi reaction involving zincated pyridazin-3(2H)-ones

J Org Chem. 2011 Dec 2;76(23):9648-59. doi: 10.1021/jo201587j. Epub 2011 Nov 9.

Authors

Tom Verhelst¹, Zuming Liu, Jens Maes, Bert U W Maes

Affiliation

¹ Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium.

PMID: 22017314
DOI: 10.1021/jo201587j

Abstract

Zincated pyridazin-3(2H)-ones generated via bromine-magnesium exchange followed by transmetalation using ZnCl(2) or via lactam-directed ortho C4-H zincation with TMPZnCl·LiCl have been synthesized. These in situ created organometallics can be used in Negishi reactions with iodo(hetero)arenes delivering a new approach toward (hetero)arylpyridazin-3(2H)-ones.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Molecular Structure
Organometallic Compounds / chemical synthesis
Organometallic Compounds / chemistry
Pyridazines / chemical synthesis*
Pyridazines / chemistry
Stereoisomerism
Zinc / chemistry*

Substances

Organometallic Compounds
Pyridazines
Zinc