K. N. Rao, K. Redda, F. Y. Onayemi
1995
Citations
0
Influential Citations
24
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
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.