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A facile thermal equilibration of cis-(3-methoxy-2-piperidyl)-Z-propanone and some analogous cis-(&substituted 2-piperidyI)-Z-propanones with their trans isomers is reported. The effects on the equilibrium of temperature, solvent, pH, and the size of the 3 substituent were investigated. Chemical and nmr spectral data and conformational free-energy calculations are presented to support the assignment of the trans configuration to the more stable isomer.The title compounds are intermediates in the synthesis of febrifugines.A revised synthesis of the title compounds is reported.

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A potent a n t i p a r a s i t i c agent 3-nitro-6-propoxyimidazo[l,2-b]oxy side chain, from n-propanol-l-"T and 6-chloro-3-nitroimidazo-pyridazine (2) was synthesized, labeled w i t h carbon-14 i n the pro-E 1,2-b]pyridazine (2). The f i n a l product was obtained i n 58% radiochemical y i e l d w i t h s p e c i f i c a c t i v i t y o f 1.13 mCi/mnole and radiochemical p u r i t y o f greater than 99%. The deuterium labeled compound (9 was also synthesized f o r absorption and metabolism studies.

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l-Methyl-4-(3-methyl-5-isoxazolyl)pyridinium chloride (1) has been found to display interesting hypoglycemic activity in laboratory animals, and is currently undergoing extensive evaluation as a potential antidiabetic drug. To facilitate the study of the bodily distribution and metabolism of 1, a radiolabelled sample was required.

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NEW COMPOUNDSNew Phenolic Mercurials1 In a study of the preparation of new phenols of possible pharmaceutical interest the following new derivatives, which include mercurials of p-f-octylmono-,1* cyclohexylidenedi-,,b and hexyl-tetraphenols,26 *have been prepared and characterized for such ions with potassium iodide solution (red precipitate of mercuric iodide soluble in excess' of reagent), the solution was then chilled in the refrigerator and the crude mono-mercurial filtered off and dried. The monomercurial was recrystallized from 50% aqueous alcohol containing 5% glacial acetic acid. The yield was about 80-85%.Chloromercurials.-These were obtained by pouring an alcoholic or a glacial acetic acid solution of the acetoxymercuri derivative into an equal volume of a 20% aqueous solution of reagent grade sodium chloride. The chloromercurial was filtered off and recrystallized from ethanol or glacial acetic acid. The yields varied from 70-90%.