Synthesis of functionalized pyridazin-3(2H)-ones via bromine-magnesium exchange on bromopyridazin-3(2H)-ones

Oxana Ryabtsova; Tom Verhelst; Mattijs Baeten; Christophe M L Vande Velde; Bert U W Maes

doi:10.1021/jo9020985

Synthesis of functionalized pyridazin-3(2H)-ones via bromine-magnesium exchange on bromopyridazin-3(2H)-ones

J Org Chem. 2009 Dec 18;74(24):9440-5. doi: 10.1021/jo9020985.

Authors

Oxana Ryabtsova¹, Tom Verhelst, Mattijs Baeten, Christophe M L Vande Velde, Bert U W Maes

Affiliation

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

PMID: 19928756
DOI: 10.1021/jo9020985

Abstract

The potential of halogen-magnesium exchange reactions, followed by quenching with electrophiles, for the functionalization of the pyridazin-3(2H)-one core was investigated. 2-Benzyl-4-bromo-5-methoxy- (1), 2-benzyl-5-bromo-4-methoxy- (4), and 2-benzyl-4,5-dibromopyridazin-3(2H)-one (10) were selected as readily available model substrates. While 1 and 10 gave exclusively C-4 metalation, a tandem reaction involving nucleophilic substitution via addition elimination and bromine-magnesium exchange was observed with 4.

Publication types

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

MeSH terms

Bromine / chemistry*
Hydrocarbons, Brominated / chemistry*
Magnesium / chemistry*
Models, Chemical
Pyridazines / chemical synthesis*
Pyridazines / chemistry
Pyridones / chemistry*

Substances

Hydrocarbons, Brominated
Pyridazines
Pyridones
Magnesium
Bromine