Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles.
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.
Pinho e Melo
Teresa M V D
TM
Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade de Coimbra, 3004-535 Coimbra, Portugal. tmelo@ci.uc.pt
Lopes
Cláudia S J
CS
Gonsalves
António M d'A Rocha
AM
Beja
Ana M
AM
Paixão
José A
JA
Silva
Manuela R
MR
da Veiga
Luiz Alte
LA