The palladium-catalysed reaction of readily accessible 2-alkynyltrifluoroacetanilides with aryl hanides and vinyl triflates under a carbon monoxide atmosphere (1 or 7 atm) the presence of potassium carbonate produce s 2-substituted-3-acyl indoles in fair to good yield. The acidity of the nitrogen-hydrogen bond proved to be of primary importance for the success of the reaction. The methodology has been applied to the synthesis of pravadoline, a drug that shows analgesic activity against postoperative pain in man.

2-Substituted-3-acylindoles through the Palladium-Catalysed Carbonylative Cyclization of 2-Alkynyltrifluoroacetanilides with Aryl Halides and Vinyl Triflates

ARCADI, Antonio;
1994

Abstract

The palladium-catalysed reaction of readily accessible 2-alkynyltrifluoroacetanilides with aryl hanides and vinyl triflates under a carbon monoxide atmosphere (1 or 7 atm) the presence of potassium carbonate produce s 2-substituted-3-acyl indoles in fair to good yield. The acidity of the nitrogen-hydrogen bond proved to be of primary importance for the success of the reaction. The methodology has been applied to the synthesis of pravadoline, a drug that shows analgesic activity against postoperative pain in man.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11697/11720
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