Synthesis of N-Substituted 4-Trimethylstannyl-3,6-dihydro- 2H-pyridines as Promising Synthons in the Preparative Chemistry of Piperidine

摘要

Piperidine derivatives are of interest due to a broad spectrum of their biological activity [1,2]. In this work, we synthesized previously unknown piperidine derivatives, N-substituted 4-trimethylstannyl-3,6-dihydro-2H-pyridines I and II starting from prepara- tively available tert-butyl or benzyl l,2,3,6-tetrahydro-4-[(trifluoromethyl)sulfonyl]pyridine-1 -carboxylates III, IV [3]. The latter react with hexamethyldistannane in the presence of catalyst systems Pd(PPh3)4-anhydrous LiCl [4] under reflux in dioxane for 1.5 h to afford I and II as pale yellow oily substances in a yield of 80-90%.