Selenium-Containing Heterocycles From Isoselenocyanates: Synthesis of 1,3-Selenazolidine and Perhydro-1,3-selenazine Derivatives

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