title: An unexpected highly stereoselective bisaziridination of (E,E)-1,4-dialkyl-2,3-dinitrobutadienes followed by a nitro group driven ring enlargement.
abstract: (+/-)-2,2'-Dinitro-2,2'-biaziridines were obtained by a direct aza-MIRC (Michael initiated ring closure) reaction on (E,E)-1,4-dialkyl-2,3-dinitro-l,3-butadienes under very mild conditions. The reactions occur with high stereoselectivity as shown by the enantioselective HPLC analyses performed on the crude mixtures. Ring enlargement to 3,3'-bi(1,2,4-oxadiazole) derivatives was easily obtained by a simple treatment with sodium iodide in DMSO, with an unforeseen regioselective aziridine C-C cleavage.
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, Università degli Studi La Sapienza, Piazzale A. Moro 5, I-00185 Roma, Italy.
authors.forename: Alessia
authors.initials: A
authors.lastname: Ciogli
authors.forename: Stefania
authors.initials: S
authors.lastname: Fioravanti
authors.forename: Francesco
authors.initials: F
authors.lastname: Gasparrini
authors.forename: Lucio
authors.initials: L
authors.lastname: Pellacani
authors.forename: Egon
authors.initials: E
authors.lastname: Rizzato
authors.forename: Domenico
authors.initials: D
authors.lastname: Spinelli
authors.forename: Paolo A
authors.initials: PA
authors.lastname: Tardella
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D002070:Butadienes / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D008956:Models, Chemical; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010069:Oxadiazoles / Q000737:chemistry; D012974:Sodium Iodide / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C547269:3,3'-bi(1,2,4-oxadiazole); D000473:Alkanes; D001388:Aziridines; D002070:Butadienes; D009574:Nitro Compounds; D010069:Oxadiazoles; D012974:Sodium Iodide; D004121:Dimethyl Sulfoxide