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Hantzsch pyrrole synthesis on solid support
A W Trautwein1, R D Süssmuth, G Jung
1Institut für Organische Chemie, Eberhard-Karls-Universität Tübingen, Germany.
Bioorganic & Medicinal Chemistry Letters
|January 5, 1999
Abstract:
An efficient method for solid-phase synthesis of pyrroles is described. Polystyrene Rink amide resin is acetoacetylated and converted into polymer bound enaminones upon treatment with primary amines. These then undergo a Hantzsch reaction with alpha-bromoketones to yield pyrroles. After cleavage with 20% trifluoroacetic acid in dichloromethane pyrrole-3-carboxamides are obtained in excellent purity.