An unexpected highly stereoselective bisaziridination of (E,E)-1,4-dialkyl-2,3-dinitrobutadienes followed by a nitro group driven ring enlargement.
(+/-)-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.
Ciogli
Alessia
A
Dipartimento di Chimica e Tecnologie del Farmaco, Università degli Studi La Sapienza, Piazzale A. Moro 5, I-00185 Roma, Italy.
Fioravanti
Stefania
S
Gasparrini
Francesco
F
Pellacani
Lucio
L
Rizzato
Egon
E
Spinelli
Domenico
D
Tardella
Paolo A
PA
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
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