Download PDF
Synfacts 2009(4): 0375-0375  
DOI: 10.1055/s-0028-1087887
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Substituted Pyrroles from Skipped Diynes

Contributor(s): Victor Snieckus, Josefine Karlsson
D. Tejedor*, S. López-Tosco, J. González-Platas, F. García-Tellado*
Instituto de Productos Naturales y Agrobiología-CSIS, Instituto Canario de Investigación del Cáncer and Universidad de La Laguna, La Laguna, Tenerife, Spain
Further Information

Publication History

Publication Date:
23 March 2009 (online)

    Permissions and Reprints

Significance

Described here is the synthesis of substituted pyrrole 2-carboxylate esters by a metal-free reaction of skipped diynes with primary amines. The key to this domino process are the Michael acceptor properties of the alkynoate. The final pyrrole products result from a [3,3]-sigmatropic rearrangement. No evidence for any of the intermediates is provided. The reaction can be performed under conventional or microwave heating, the first being a slightly more efficient reaction but the latter being faster (30 min).