title: Tandem reactions of 1,2,4-oxadiazoles with allylamines.
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.
authors.affiliation: Dipartimento 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
authors.forename: Antonio
authors.initials: A
authors.lastname: Palumbo Piccionello
authors.forename: Andrea
authors.initials: A
authors.lastname: Pace
authors.forename: Silvestre
authors.initials: S
authors.lastname: Buscemi
mesh_terms: D000499:Allylamine / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis / Q000737:chemistry*; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D010069:Oxadiazoles; D011743:Pyrimidines; D000499:Allylamine