Reaction of 2,3-disubstituted-N-arylsulfonylaziridines with isocyanates in presence of sodium iodide - stereospecific conversion of N-arylsulfonylaziridines to imidazolidinones

Synthetic Applications and Methodological Developments of Donor−Acceptor Cyclopropanes and Related Compounds

“…[47] While these types of reactions were known at the outset of this work, there existed few examples using easily derivatizable N -sulfonylaziridines, [48] and only a single example of a stereoselective reaction. [49] …”

“…In addition to our work on cycloadditions of donor–acceptor cyclopropanes with heterocumulenes, we sought access to more highly nitrogenated heterocycles by replacing the cyclopropanes with related activated aziridines. [47] While these types of reactions were known at the outset of this work, there existed few examples using easily derivatizable N -sulfonylaziridines, [48] and only a single example of a stereoselective reaction. [49]…”

Some Synthetic Uses of Double‐Bonded Functional Groups

“…The reaction usually gives a stereocontrolled product in up to 60% yield (equation 200) 714 (200) Carboximidoyl chlorides may be reacted with oximes to give 30 65% yield of amidines, which may then be used to form imidazoles in good yields, by treatment with TsOH (equation 201) 716 . Highly substituted imidazoles may be prepared in a simple one-pot synthesis by treating vicinal tricarbonyl compounds with an aldehyde and ammonium acetate (equation 202) 717 .…”

Synthesis and Antiproliferative Activity of Phosphorus Substituted 4-Cyanooxazolines, 2-Aminocyanooxazolines, 2-Iminocyanooxazolidines and 2-Aminocyanothiazolines by Rearrangement of Cyanoaziridines

“…Furthermore, the ring-expansion of aziridines with isocyanates has been revealed to be a useful pathway for the synthesis of a variety of five-membered nitrogen-containing compounds. For instance, KI [ 17 ], NaI [ 18 , 19 , 20 ], NiI 2 [ 21 ], Pd-catalyzed [ 22 , 23 , 24 ] reactions of aziridines with isocyanates, or even in the absence of catalysts [ 25 ], have been described. All these reactions yielded imidazolidin-2-ones or oxazolidin-2-imines compounds which generate great interest in medicinal and pharmaceutical chemistry since they represent classes of heterocyclic compounds with a broad variety of biological activities [ 26 , 27 ].…”