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

The Journal of Organic Chemistry
Oxana RyabtsovaBert U W Maes

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.

References

Apr 3, 2001·The Journal of Organic Chemistry·R K DieterL E Nice
Feb 1, 2006·Chemical Communications : Chem Comm·Hiriyakkanavar IlaPaul Knochel

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