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Synthesis of Substituted Pyrroles from Skipped Diynes
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
23 March 2009 (online)
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).