Salta al contenuto principale
Passa alla visualizzazione normale.

ANTONIO PALUMBO PICCIONELLO

Tandem Reactions of 1,2,4-Oxadiazoles with Allylamines

  • Autori: Palumbo Piccionello, A; Pace, A; Buscemi, S
  • Anno di pubblicazione: 2011
  • Tipologia: Articolo in rivista (Articolo in rivista)
  • Parole Chiave: ANRORC, Oxadiazoles, cycloadditions
  • OA Link: http://hdl.handle.net/10447/63145

Abstract

A reaction of 3-chloro-1,2,4-oxadiazoles with allylamine and diallylamine has been investigated. 3,3a,4,5-Tetrahydroisoxazolo[3,4-d]pyrimidines are produced through a tandem ANRORC/[3þ2]cycloaddition pathway consisting of the addition of allylamine to the 1,2,4-oxadiazole, followed by ring opening, nitrone formation, and finally cycloaddition. 3-N-Allylamino-1,2,4-oxadiazoles were also obtained as minor products through a classical SNAr. Conversely, a reaction with diallylamine produces 3-N,N-diallylamino-1,2,4-oxadiazole and imidazoline through tandem SNAr/ aziridination and nucleophilic ring opening.