Efficient pyrrolidine catalyzed cycloaddition of aziridines with isothiocyanates, isoselenocyanates and carbon disulfide “on water”

Abstract

The cycloaddition of aziridines with isothiocyanates, isoselenocyanates and carbon disulfide is described using pyrrolidine on water. This protocol affords a potential route for the construction of the five membered heterocycles with high yields.

Ring Expansions of Activated Aziridines and Azetidines

“…Punniyamurthy and co-workers developed a mild synthetic route towards iminothiazolidines through pyrrolidine-catalyzed cycloaddition reaction of unactivated and activated aziridines with isothiocyanates in aqueous medium under air at moderate temperature [151].…”

Isosorbide bis(methyl carbonate) synthesis from isosorbide and dimethyl carbonate: the key role of dual basic–nucleophilic catalysts

“…28 Finally, the piperidineand pyrrolidine-catalyzed cycloaddition of 1-isopropyl-2phenylaziridine with phenyl isothiocyanate to yield the desired thiazolidin-2-ylidene, in which a highly reactive ureatype intermediate is formed by reaction of the catalyst and the isothiocyanate in a rst step, which in a second step reacts with the azidirine to yield the desired product with catalyst regeneration constitutes another example of a highly reactive reactant-catalyst intermediate needed to complete the desired reaction. 29…”

Recent applications of aziridine ring expansion reactions in heterocyclic synthesis

“…82 This reaction goes through a urea-type intermediate 152, which on reaction with aziridine through an S N 2 reaction afforded product 153. The intramolecular cyclization of the product 153 provided heterocycles 151 (Scheme 46).…”