Synthesis of Polysubstituted Pyrroles

Celine      Poulard; Julien      Cornet; Stephanie      Legoupy; Gilles      Dujardin; Robert      Dhal; Francois      Huet

doi:10.2174/157017809788681338

Abstract

Cross coupling metathesis reactions from two ethylenic compounds 4 and 5 easily led to Michael acceptors 6ab and 7a-b. Reaction of these compounds, or of enone 5, with p-toluenesulfonylmethyl isocyanide (TosMIC) provided the disubstituted pyrroles 9a-c and 10a-b. The analogous reaction of compounds 6a-b and 5, but in presence of Ph3SnCl, provided the trisubstituted pyrroles 11a-c. All of these compounds 9-11 were thus obtained in two steps only.

Keywords: Lavendamycin, pyrroles, TosMIC, Michael acceptors, cross metathesis

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Letters in Organic Chemistry

Title: Synthesis of Polysubstituted Pyrroles

Volume: 6 Issue: 5

Author(s): Celine Poulard, Julien Cornet, Stephanie Legoupy, Gilles Dujardin, Robert Dhal and Francois Huet

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Keywords: Lavendamycin, pyrroles, TosMIC, Michael acceptors, cross metathesis

Abstract: Cross coupling metathesis reactions from two ethylenic compounds 4 and 5 easily led to Michael acceptors 6ab and 7a-b. Reaction of these compounds, or of enone 5, with p-toluenesulfonylmethyl isocyanide (TosMIC) provided the disubstituted pyrroles 9a-c and 10a-b. The analogous reaction of compounds 6a-b and 5, but in presence of Ph3SnCl, provided the trisubstituted pyrroles 11a-c. All of these compounds 9-11 were thus obtained in two steps only.

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Poulard Celine, Cornet Julien, Legoupy Stephanie, Dujardin Gilles, Dhal Robert and Huet Francois, Synthesis of Polysubstituted Pyrroles, Letters in Organic Chemistry 2009; 6 (5) . https://dx.doi.org/10.2174/157017809788681338