Selenium-containing heterocycles from isoselenocyanates: Synthesis of 1,3-selenazolidine and perhydro-1,3-selenazine derivatives

Abstract

Treatment of ω-halo alkylamines 9 and 10 with aryl and alkyl isoselenocyanates 6a-g in the presence of triethylamine in dichloromethane gave the corresponding 1,3-selenazolidines 11a-g and perhydro-1,3-selenazines 12a-g, respectively, in good to excellent yields. Chemical and spectroscopic evidence for the structures of all new compounds are presented, and in selected examples the molecular structures have been established by X-ray crystallography. The analogous reactions with isothiocyanates have been used for the preparation of 1,3-thiazolidines and perhydro-1,3-thiazines. © Wiley-VCH Verlag GmbH & Co. KGaA, 2005.