40995-48-0

Usage

Class of compound

pyrazolo[3,4-d]pyridazin-4-one derivative (a heterocyclic compound)

Known for

potential biological activity and pharmaceutical applications

Also used as

a building block for the synthesis of other organic compounds in research laboratories

Specific properties and uses

depend on the application and intended use in various fields of chemistry and biochemistry.

Upstream product

• 186581-53-3 diazomethane 
• 22687-56-5 2-methylpyridazin-3(2H)-one 
• 14628-34-3 5-chloro-2-methyl-3(2H)-pyridazinone 
• 67264-09-9 5-Bromo-2-methyl-2H-pyridazin-3-one 

Relevant academic research and scientific papers

1,3-Dipolar cycloaddition of diazomethane to differently substituted 2-methylpyridazin-3(2H)-ones

Cycloaddition of diazomethane to 4- or 5-substituted 2-methylpyridazin-3 (2H)-ones 1,2 occurs in a practically regiospecific manner to give the expected adducts, which are not stable enough to be isolated and under the reaction conditions are transformed into N, N′-dimethylpyrazolopyridazinones and/or 2,4 (or 2,5)-dimethylpyridazin-3(2H)-ones, depending on the nature and position of the substituents. The regiochemistry of the cycloaddition and the reactivity of pyridazin-3 (2H)-ones 1,2 have been accounted for theoretically by the FMO approach.

PYRAZOLOPYRIDAZINONES BY 1,3-DIPOLAR CYCLOADDITION OF DIAZOMETHANE TO PYRIDAZIN-3(2H)-ONES

N-methylpyridazin-3(2H)-ones 1-3 react slowly with diazomethane to give, as main products, the N,N'-dimethylpyrazolopyridazin-4(5H)-ones 10a and 10 b in a 1 : 2 ratio.The reaction of diazomethane with the N-methyl-4-bromopyridazin-3(2H)-one (4) leads to N1,N6-dimethylpyrazolopyridazin-7(6H)-one (9a).In the first case, the regioselectivity of the primary 1,3-dipolar cycloaddition is the reverse of that observed in enone systems.