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

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

Journal Name: Letters in Organic Chemistry

Volume 1 , Issue 4 , 2004

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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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Article Details

Year: 2004
Page: [369 - 371]
Pages: 3
DOI: 10.2174/1570178043400695
Price: $58