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Pinho e Melo TM, Lopes CS, Gonsalves AM, et al. Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles. J Org Chem. 2002;67(1):66-71doi: 10.1021/jo010504v.
Pinho e Melo, T. M., Lopes, C. S., Gonsalves, A. M., Beja, A. M., Paixão, J. A., Silva, M. R., & da Veiga, L. A. (2002). Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles. The Journal of organic chemistry, 67(1), 66-71. https://doi.org/10.1021/jo010504v
Pinho e Melo, Teresa M V D, et al. "Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles." The Journal of organic chemistry vol. 67,1 (2002): 66-71. doi: https://doi.org/10.1021/jo010504v
Pinho e Melo TM, Lopes CS, Gonsalves AM, Beja AM, Paixão JA, Silva MR, da Veiga LA. Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles. J Org Chem. 2002 Jan 11;67(1):66-71. doi: 10.1021/jo010504v. PMID: 11777440.
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J Org Chem. 2002 Jan 11;67(1):66-71. doi: 10.1021/jo010504v.

Reactivity of 2-halo-2H-azirines. 1. Reactions with nucleophiles.

The Journal of organic chemistry

Teresa M V D Pinho e Melo, Cláudia S J Lopes, António M d'A Rocha Gonsalves, Ana M Beja, José A Paixão, Manuela R Silva, Luiz Alte da Veiga

Affiliations

  1. Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade de Coimbra, 3004-535 Coimbra, Portugal. [email protected]

PMID: 11777440 DOI: 10.1021/jo010504v

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.

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