Synthesis of Functionalized Pyridazin-3(2H)-ones via Bromine−Magnesium Exchange on Bromopyridazin-3(2H)-ones

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 selecte...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-12, Vol.74 (24), p.9440-9445
Main Authors: Ryabtsova, Oxana, Verhelst, Tom, Baeten, Mattijs, Vande Velde, Christophe M. L, Maes, Bert U. W
Format: Article
Language:English
Subjects:
Bromine - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Hydrocarbons, Brominated - chemistry
Magnesium - chemistry
Models, Chemical
Organic chemistry
Preparations and properties
Pyridazines - chemical synthesis
Pyridazines - chemistry
Pyridones - chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9020985