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 α-diimines 7 and 8. 2-Halo-2H-azirines wer...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-01, Vol.67 (1), p.66-71
Main Authors: Pinho e Melo, Teresa M. V. D, Lopes, Cláudia S. J, Beja, Ana M, Paixão, José A, Silva, Manuela R, Alte da Veiga, Luiz
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo010504v