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Updated: May 30, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Tandem reactions of 1,2,4-oxadiazoles with allylamines
Antonio Palumbo Piccionello1, Andrea Pace, Silvestre Buscemi
1Dipartimento di Scienze e Tecnologie Molecolari e Biomolecolari (STEMBIO), Sez. Chimica Organica, Università degli Studi di Palermo, Viale delle Scienze, Parco d'Orleans II, Ed. 17, I-90128 Palermo, Italy. apalumbo@unipa.it
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/[3 + 2]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.
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