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RESEARCH PRODUCT

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

Andrea PaceSilvestre BuscemiAntonio Palumbo-piccionello

subject

chemistry.chemical_classificationOxadiazolesMolecular StructureTandemChemistryOrganic ChemistryImidazoline receptorStereoisomerismSettore CHIM/06 - Chimica OrganicaRing (chemistry)BiochemistryMedicinal chemistryCycloadditionAllylamineAllylamineNitronechemistry.chemical_compoundANRORC Oxadiazoles cycloadditionsPyrimidinesNucleophileCyclizationNucleophilic aromatic substitutionPhysical and Theoretical Chemistry

description

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.

yearjournalcountryeditionlanguage
2011-08-11
10.1021/ol201676ghttp://hdl.handle.net/10447/63145