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Novel benzamide derivatives, N-[1-(aminocarbonyl)-2-(1-piperidinyl)ethyl]benzamides (4 and 5), were prepared from the reaction of beta-piperidinoalanine (6) as the starting material.

The reductions of an α, β-unsaturated lactone (5) and lactam (7) with the Ni2+/BH-4 system resulted in the formation of cis-hydrogenated products (8a and 9a) with high stereoselectivity. The cis products (8a and 9a) were easily isomerized to the corresponding trans isomers (8b and 9b, respectively) by refluxing with sodium methoxide in anhydrous methanol. Isotope labeling studies with methyl cinnamate as the substrate indicated that the reduction with this reducing system poceeds stepwise via a carbon-nickel intermediate. more...

A facile ring transformation of 1, 2, 3, 5, 6, 7-hexahydropyrrolizinium perchlorates (1 and 2) to 1-substituted 5-oxoperhydroazocines (5) is described. The spectroscopic and chemical properties of these products are also presented. more...

Preparation of β-(sec-amino)alanines (3) by acid hydrolysis of diethyl (sec-aminomethyl)formamidomalonates (2) was studied. Although high reaction temperature resulted in low yield, low reaction temperature (below 30°C) gave good to excellent yields. The hydrolysis of diethyl formamido(piperidinomethyl)malonate (2a) was followed by 1H-NMR, and a plausible mechanism involving the condensation of ethyl hydrogen aminomalonate (7) with 1-piperidinemethanol (5) is proposed. more...

A nucleophilic addition of phenol to N-(2-pyridylmethylene) aniline (I) is described. Electron density around carbon atom ortho to phenolic hydroxyl group and acidity of phenol are the two factors governing the outcome of the reaction. The effects of structural variation of Schiff base on its reactivity are also discussed. Extension of the reaction involved addition of 8-hydroxyquinoline to the Schiff base (I). more...

A new method for the syntheses of 1, 2-dipyridylethylene and its derivatives is described. The method involves condensation between N-oxides of picoline, lutidine, and quinaldine and pyridinemethanol in the presence of potassium hydroxide. Some stilbazole syntheses were also described. more...

A new synthesis of N-(2-pyridylmethylene) aniline (I) is described. The method consists of heating a mixture of 2-pyridinemethanol, aniline, and nitrobenzene in the presence of potassium hydroxide. Extension of the reaction to some related compounds was made. By-products accompanied with ortho-substituted derivatives of I were characterized as pyridylmethylene-bis-amines. more...