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Reactivity of 2-Halo-2H-azirines. 1. Reactions with Nucleophiles
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.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 1...
Synthesis of 2-halo-2H-azirines
Pinho e Melo, Teresa M. V. D.; Lopes, Cláudia S. J.; Cardoso, Ana L.; Rocha Gonsalves, António M. d'A.[alpha]-Oxophosphonium ylides react with N-chlorosuccinimide, N-bromosuccinimide and N-iodosuccinimide in the presence of azidotrimethylsilane giving the corresponding haloazidoalkenes which were completely converted to the 2-halo-2H-azirines on heating in heptane. ; http://www.sciencedirect.com/science/article/B6THR-43J0SY1-D/1/db29a4ddcbdab643bfdc11154aaf101f
Synthesis and reactivity of 2-halo-2H-azirines towards nucleophiles
Pinho e Melo, Teresa M. V. D.; Lopes, Cláudia S. J.; Gonsalves, António M. d'A. RochaNucleophilic substitution reactions of 2-halo-2H-azirine with potassium phthalimide and aniline allowed the preparation of new substituted 2H-azirines. The reactions of 2-bromo-3-phenyl-2H-azirine-2-carboxylate with methylamine led to the synthesis of [alpha]-diimines and from the reaction with water, a 3-oxazoline was obtained. ; http://www.sciencedirect.com/science/article/B6THS-4152YMR-K/1/e94005b66b66b68...
Synthesis of 2-halo-2H-azirines from phosphorus ylides
Melo, Teresa M. V. D. Pinho e; Gonsalves, António M. D'A. Rocha; Lopes, Cláudia S. J.; Gilchrist, Thomas L.[alpha]-Oxophosphonium ylides (3a-3e) react with N-chlorosuccinimide and N-bromosuccinimide in the presence of azidotrimethylsilane giving the corresponding haloazidoalkenes (4a-4g) with elimination of triphenylphosphine oxide. These compounds were completely converted to the 2H-azirines 5a-5g on heating in heptane. ; http://www.sciencedirect.com/science/article/B6THS-3VXSK6D-3T/1/9eb19b08a4875f23803d57d6eca...
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