title: Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles.
abstract: Nucleophilic substitution reactions of 2-halo-2H-azirines 1a, 1b, 1d, and 1e with potassium phthalimide and aniline allowed the preparation of new substituted 2H-azirines 2-5. The reactions of 2-bromo-2H-azirine 1a with methylamine led to the synthesis of alpha-diimines 7 and 8. 2-Halo-2H-azirines were also established as building blocks for the synthesis of a range of heterocyclic compounds, namely, quinoxalines 10a-10d, 3-oxazoline 14, and 2H-[1,4]oxazines 18 and 20. X-ray crystal structures of alpha-diimine 7, 3-oxazoline 14, and 2H-[1,4]oxazine 18 are reported.
authors.affiliation: Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade de Coimbra, 3004-535 Coimbra, Portugal. tmelo@ci.uc.pt
authors.forename: Teresa M V D
authors.initials: TM
authors.lastname: Pinho e Melo
authors.forename: Cláudia S J
authors.initials: CS
authors.lastname: Lopes
authors.forename: António M d'A Rocha
authors.initials: AM
authors.lastname: Gonsalves
authors.forename: Ana M
authors.initials: AM
authors.lastname: Beja
authors.forename: José A
authors.initials: JA
authors.lastname: Paixão
authors.forename: Manuela R
authors.initials: MR
authors.lastname: Silva
authors.forename: Luiz Alte
authors.initials: LA
authors.lastname: da Veiga