Behaviour of Thiophenes Substituted with Electron-Withdrawing Groups in Cycloaddition Reactions

Claudia   Della   Rosa; Elisa      Paredes; Maria      Kneeteman; Pedro   M.E.   Mancini

doi:10.2174/1570178043400695

Abstract

Substituted thiophenes can act as dienophiles in normal electron demand Diels-Alder reactions, nitro being one of the substituents. Cycloaddition with Danishefskys diene provides the benzothiophene derivatives with nitro side selectivity, α-substituted substrates being the more dienophilic. The reaction with isoprene leads mainly to the corresponding (pyrrol-1-yl)thiophenes.

Keywords: thiophenes, diels-alder, pyrroles, benzothiophenes

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Letters in Organic Chemistry

Title: Behaviour of Thiophenes Substituted with Electron-Withdrawing Groups in Cycloaddition Reactions

Volume: 1 Issue: 4

Author(s): Claudia Della Rosa, Elisa Paredes, Maria Kneeteman and Pedro M.E. Mancini

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Keywords: thiophenes, diels-alder, pyrroles, benzothiophenes

Abstract: Substituted thiophenes can act as dienophiles in normal electron demand Diels-Alder reactions, nitro being one of the substituents. Cycloaddition with Danishefskys diene provides the benzothiophene derivatives with nitro side selectivity, α-substituted substrates being the more dienophilic. The reaction with isoprene leads mainly to the corresponding (pyrrol-1-yl)thiophenes.

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Rosa Della Claudia, Paredes Elisa, Kneeteman Maria and Mancini M.E. Pedro, Behaviour of Thiophenes Substituted with Electron-Withdrawing Groups in Cycloaddition Reactions, Letters in Organic Chemistry 2004; 1 (4) . https://dx.doi.org/10.2174/1570178043400695