Hantzsch pyrrole synthesis on solid support.
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.
Trautwein
A W
AW
Institut für Organische Chemie, Eberhard-Karls-Universität Tübingen, Germany.
Süssmuth
R D
RD
Jung
G
G
D000090:Acetoacetates; D002625:Chemistry, Organic / Q000379:methods*; D015195:Drug Design; D005449:Fluorenes; D007202:Indicators and Reagents; D010627:Phenethylamines / Q000737:chemistry; D011137:Polystyrenes; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D012117:Resins, Synthetic; D013329:Structure-Activity Relationship
D000090:Acetoacetates; D005449:Fluorenes; D007202:Indicators and Reagents; D010627:Phenethylamines; D011137:Polystyrenes; D011758:Pyrroles; D012117:Resins, Synthetic; C075825:Rink amide resin