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Synthesis 2009(14): 2403-2407  
DOI: 10.1055/s-0029-1216846
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Functionalized N-Vinyl Nitrogen-Containing Heterocycles

Susana M. M. Lopesa, Ana Matos Bejab, Manuela Ramos Silvab, José A. Paixãob, Francisco Palaciosc, Teresa M. V. D. Pinho e Melo*a
a Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal
Fax: +351(239)827703; e-Mail: tmelo@ci.uc.pt;
b Department of Physics, University of Coimbra, 3004-516 Coimbra, Portugal
c Department of Organic Chemistry I, Faculty of Pharmacy, University of the Basque Country, Apartado 450, 01080 Vitoria, Spain
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Publication History

Received 2 February 2009
Publication Date:
29 May 2009 (online)

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Abstract

Microwave-assisted 1,3-dipolar cycloaddition of the azomethine ylide generated by ring opening of a N-vinylaziridine gave new N-vinyl derivatives of pyrrolidine, 3-pyrroline, octahydropyrrolo[3,4-c]pyrrole and 1,2,4-triazolidine.

Key words

microwave-assisted 1,3-dipolar cycloaddition - Michael addition - allenes - N-vinyl heterocycles - aziridines - pyrrolidines - 3-pyrrolines - octahydropyrrolo[3,4-c]pyrroles - 1,2,4-triazolidines

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