5538-02-3

Upstream product

• 20375-65-9 3-chloro-6-phenylpyradazine 
• 124-38-9 carbon dioxide 
• 74-88-4 methyl iodide 
• 181265-77-0 2-bromoacetophenone t-butoxycarbonyl hydrazone 
• 808798-00-7 N'-(2-bromo-1-phenylethylidene)acetohydrazide 
• 108-59-8 malonic acid dimethyl ester 

Relevant academic research and scientific papers

Addition of malonic esters to azoalkenes generated in situ from α-bromo- and α-chlorohydrazones

Michael addition of malonic esters to azoalkenes generated in situ from α-bromo- and α-chlorohydrazones was accomplished. Both aliphatic and aromatic substrates bearing different functional groups are tolerated. The use of a strong base (sodium hydride) for generation of azoalkenes and deprotonation of malonate was found to be essential for a successful coupling. Synthetic potential of the obtained β-hydrazonoalkylmalonates was demonstrated by their smooth conversion into five- and six-membered N-heterocycles, functionalized hydrazides, 2-(2-oxo-2-arylethyl)malonates and 2-arylethylmalonates.

Electrochemical Carboxylation of Some Heteroaromatic Compounds

Thirty heteroaromatic compounds have been investigated by cyclic voltammetry (CV) and/or preparative scale electrolysis (PSE) in the absence and presence of carbon dioxide.The rate constants of dehalogenation of the primarily formed anion radical of halogenated heterocycles were estimated from cyclic voltammetric data; these data indicated that carboxylation without loss of chlorine is possible under cyclic voltammetric conditions when the rate constant of cleavage is less than about 104 s-1.PSE confirmed that such halogenated heterocycles may be reductively carboxylated without loss of halogen.In the competition between cleavage and carboxylation low temperatures favour the latter reaction.