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.
Palumbo Piccionello, A., Pace, A., Buscemi, S. (2011). Tandem Reactions of 1,2,4-Oxadiazoles with Allylamines. ORGANIC LETTERS, 13(13), 4749-4751 [10.1021/ol201676g].
Tandem Reactions of 1,2,4-Oxadiazoles with Allylamines
PALUMBO PICCIONELLO, Antonio;PACE, Andrea;BUSCEMI, Silvestre
2011-01-01
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.
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