Synthesis 2005(4): 555-558  
DOI: 10.1055/s-2004-837296
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

M. José Alves*a, A. Gil Fortes*a, Américo Lemosb, Cristina Martinsa
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
Further Information

Publication History

Received 7 September 2004
Publication Date:
22 December 2004 (eFirst)

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.

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