Ethyl 2-(Diisopropoxyphosphoryl)-2H-Azirine-3-Carboxylate: Reactions with Activated 1,3-Butadienes

M. José Alves; Américo Lemos; José Rodriguez-Borges; Xerardo García-Mera

doi:10.3390/ecsoc-12-01222

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Ethyl 2-(Diisopropoxyphosphoryl)-2H-Azirine-3-Carboxylate: Reactions with Activated 1,3-Butadienes

M. José Alves

^{*

1},

Américo Lemos

²,

José Enrique Rodriguez-Borges

³,

Xerardo García-Mera

⁴

¹ Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal
² Departamento de Química, Bioquímica e Farmácia, Universidade do Algarve, Campus de Gambelas, 8005-137 Faro, Portugal
³ CIQ, Departamento de Química, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal
⁴ Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, E-15782 Santiago de Compostela, Spain

Published: 14 November 2008 by MDPI in The 12th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-12-01222

Abstract: Ethyl 2-(diisopropoxyphosphoryl)-2H-azirine-3-carboxylate was generated “in situ” and reacted with a number of 1,3-butadienes. Cycloadducts, or in one case an ensuing rearranged product, were isolated with moderate to good yields.

Keywords: 2H-Azirines, aza-Diels-Alder cycloaddition, dienophiles, phosphonate derivative compounds

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M. José Alves

Américo Lemos

José Rodriguez-Borges

Xerardo García-Mera