Reactivity of 2-Halo-2H-azirines. 1. Reactions with Nucleophiles

• Author(s): Melo, Teresa M. V. D. Pinho e ; Lopes, Cláudia S. J. ; Gonsalves, António M. d'A. Rocha ; Beja, Ana M. ; Paixão, José A. ; Silva, Manuela R. ; Veiga, Luiz Alte da
• Date: 2002
• Persistent ID: http://hdl.handle.net/10316/10283
• Origin: Estudo Geral - Universidade de Coimbra
• Document Type: Article
• Language: English

Description

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 α-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 α-diimine 7, 3-oxazoline 14, and 2H-[1,4]oxazine 18 are reported. http://dx.doi.org/10.1021/jo010504v