Synthesis Utilizing Reducing Ability of Carbon Monoxide. New Methods for Synthesis of N-Substituted Selenoamides

Abstract Convenient one-pot syntheses of N-substituted selenoamides (2) from nitriles, metallic selenium, carbon monoxide, water, and amines have been developed on the basis of an amino-group-exchange reaction of in situ formed N-unsubstituted selenoamides (1) with primary or secondary amines. The reactions consist of two processes, i.e., the formation of selenoamides 1 by the reaction of nitriles and H2Se formed from selenium, carbon monoxide and water, and the subsequent amino-group-exchange reaction of 1 with aliphatic amines. The obtained 2 are generally stable enough to be kept for several weeks under the atmosphere of nitrogen at 0 °C without any appreciable degradation. In the cases of primary amines, the corresponding selenoamides were also obtained from nitriles, selenium, carbon monoxide, and primary amines by a single-step mixing at the beginning of the reaction.