Synthesis of someN-[pyridyl(phenyl)carbonylamino]hydroxyalkyl-(benzyl)-1,2,3,6-tetrahydropyridines as potential anti-inflammatory agents

Autor:	Kode Nageswara Rao, Folakemi Y. Onayemi, Kinfe K. Redda, Hailemichael Melles, Jongoh Choi
Rok vydání:	1995
Předmět:	chemistry.chemical_compound Hydrolysis Sodium borohydride Ethanol chemistry medicine.drug_class Organic Chemistry medicine Hydroxymethyl Pyridinium Medicinal chemistry Anti-inflammatory Derivative (chemistry)
Zdroj:	Journal of Heterocyclic Chemistry. 32:307-315
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570320151
Popis:	1,2,3,6-Tetrahydropyridines are known to possess analgesic, anti-inflammatory, hyperglycemic and hypoglycemic activities. Substituted 2,4-dinitrophenylpyridinium chlorides 3 were formed by reacting 1-chloro-2,4-dinitrobenzene with hydroxypropyl, hydroxymethyl and benzyl substituted pyridines 2. Attack of the pyridinium chlorides 3 with pyridylcarbonyl hydrazides or benzoyl hydrazides 4 gave the isolable 2,4-dinitroanilino derivative 5 which underwent hydrolysis when refluxed in water:p-dioxane mixture (1:4 v/v) to afford the pyridinium ylides 6. Sodium borohydride reduction of 6 in absolute ethanol at 0° for 4–6 hours resulted in the isolation of the 1,2,3,6-tetrahydropyridines 7 in good yields.
Databáze:	OpenAIRE
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