Synthesen und pharmakologische Eigenschaften von 2,2‐Dialkyl‐5‐aryl‐3‐pyridylpyrrolidinen

Abstract

Syntheses and Pharmacological Properties of 2,2‐Dialkyl‐5‐aryl‐3‐pyridylpyrrolidines Reaction of the photochemically generated benzonitrile methylides 2 with vinylpyridines yields 2‐aryl‐4‐pyridyl‐1‐pyrrolines 3. Depending on reduction methods, the compounds 3 are selectively transformed to the corresponding cis ‐ or the trans ‐substituted pyrrolidines 10 or 11 , respectively. Furthermore, a non‐photochemical synthesis has been developed: the easily available nitro‐ketones 8 provide through reductive cyclization the pyrrolines 3 or directly the pyrrolidines 11. Twenty‐seven compounds of types 10 and 11 have been evaluated in the writhing, hot plate and kaolin tests; especially the cis ‐pyrrolidines 10 exhibit a valuable antinociceptive activity. Some of the pyrrolines and pyrrolidines have been separated into their enantiomers, which are easily interconverted.