Base-promoted cascade reaction of isocyanides, selenium and amines: a practical approach to 2-aminobenzo[d][1,3]selenazines under metal-free conditions

Abstract

An efficient method for the construction of 2-aminobenzo[d][1,3]selenazines under metal-free conditions was established.

Base-Promoted Multicomponent Reactions: A Synthesis of 2-Amino-1,3-selenazole Derivatives

“…In recent years, the construction of nitrogen-containing heterocyclic compounds by multicomponent reactions involving functional isocyanides has attracted much attention. More recently, our group reported the cascade multicomponent reactions of isocyanides, selenium, and amines for the synthesis of 2-aminobenzo­[ d ]­[1,3]­selenazines (Scheme B). Inspired by this work, we envisioned the use of α,β-unsaturated isocyanides to construct five-membered nitrogen heterocycles.…”

Iodide-Catalyzed Selenium-Assisted Sequential Multicomponent Synthesis of a Luminescence Benzo-Oxazino-Isoindole Framework

“…Initially, isocyanide 2 reacts with selenium to give isoselenocyanate 5 in the presence of Et 3 N . Selenourea 6 could be formed by the reaction of 5 and amine 3 . , Azaselenoenolate I is produced by the acid–base reaction of selenoureas 6 and Et 3 N. The oxidation of I with molecular oxygen followed by homocoupling gives diselenides II . The rearrangement of compound 1 to radical anion 7 in the presence of the iodide ion is well-known .…”

Polyselenoureas via Multicomponent Polymerizations Using Elemental Selenium as Monomer

“…Its synthesis proceeds via the multicomponent reaction of elemental selenium, isocyanides, and amines to form selenoureas with 100% atom economy. This process is analogous to isoselenocyanate chemistry, whereby isocyanides are reacted with elemental black selenium powder to form isoselenocyanates. , We demonstrate that this simple methodology proceeds rapidly under atmospheric conditions at ambient temperature in the presence of various amine monomers. Isoselenocyanates are generated in situ upon the reaction of the elemental selenium with the isocyanides, subsequently reacting with the amine moieties forming the selenourea linking motifs.…”