Ethyl 3-(2-Pyridyl)-2H-azirine-2-carboxylate: Synthesis and Reaction with Dienes

M. José Alves; A. Gil Fortes; Américo Lemos; Cristina Martins

doi:10.1055/s-2004-837296

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Ethyl 3-(2-Pyridyl)-2H-azirine-2-carboxylate: Synthesis and Reaction with Dienes

M. José Alves*^a, A. Gil Fortes*^a, Américo Lemos^b, Cristina Martins^a
^a Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal
Fax: +351(253)678983; e-Mail: mja@quimica.uminho.pt; gilf@quimica.uminho.pt;
^b Departamento de Química e Bioquímica, Universidade do Algarve, Campus de Gambelas, 8000-117 Faro, Portugal

Abstract

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Abstract

Ethyl 3-(2-pyridyl)-2H-azirine-2-carboxylate, the first example of an 3-heteroamatic 2H-azirine has been prepared. The reaction of ethyl 3-(2-pyridyl)-2H-azirine-2-carboxylate with conjugated 1,3-dienes, under mild conditions and in the absence of Lewis acid catalyst, afforded cycloadducts in good yield and high stereoselectivity.

Key words

3-heteroaromatic-2H-azirines - hetero Diels-Alder reaction - Neber reaction

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