188482-71-5

Upstream product

• 39996-51-5 N-amino-4-benzoylpyridinium mesitylenesulfonate 
• 98-88-4 benzoyl chloride 
• 14548-46-0 4-Benzoylpyridine 

Downstream Products

• 1337985-04-2 (2-cyclohexenylpyrazolo[1,5-a]pyridin-5-yl)(phenyl)methanone 

Relevant academic research and scientific papers

Highly efficient synthesis of o-(2,4-dinitrophenyl)hydroxylamine. Application to the synthesis of substituted N-benzoyliminopyridinium ylides

An efficient two-step synthesis of O-(2,4-dinitrophenyl)hydroxylamine is described along with a comparison of its aminating efficiency with O-mesitylenesulfonylhydroxylamine (MSH). It was used in an expedient N-amination/benzoylation procedure involving various substituted pyridines, leading to polysubstituted N-benzoyliminopyridinium ylides, and the scope of its amination power was studied.

Synthesis of 2- and 2,3-substituted Pyrazolo[1,5- a ]pyridines: Scope and mechanistic considerations of a domino direct alkynylation and cyclization of n -iminopyridinium ylides using alkenyl bromides, alkenyl iodides, and alkynes

Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a] pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.

Synthesis and anti-inflammatory activity determinations of some N-(substituted phenylcarbonylamino)-4-(1-hydroxymethylphenyl)-1,2,3,6-tetrahydropyridines

Several novel N-(substituted phenylcarbonylamino)-4-(1-hydroxymethylphenyl)-1,2,3,6-tetrahydropyridines were synthesized via sodium borohydride reduction of the corresponding N-(substituted phenylcarbonylimino)-4-benzoylpyridinium ylides in absolute ethanol. The anti-inflammatory activities using the carrageenan-induced rat paw edema assay and hyperglycemic effects measured by determining the rat blood glucose levels of these compounds were investigated. The unsubstituted derivative, N-phenylcarbonylamino-4-(1-hydroxymethylphenyl)-1,2,3,6-tetrahydropyridine (6a) and N-(4-chlorophenylcarbonyl-amino)-4-(1-hydroxymethyl-phenyl)-1,2,3,6- tetrahydropyridine (6e) were found to be the most active anti-inflammatory agents and their effects were comparable to that of indomethacin, the reference compound. All the compounds tested displayed moderate to good hyperglycemic activities.