Collect. Czech. Chem. Commun. 1994, 59, 1400-1407

Reaction of Ethyl 5-Substituted-2-furoylmalonates with Secondary Amines

Rudolf Kada, Jarmila Bruncková and Pavol Bobál'

Department of Organic Chemistry, Slovak Technical University, 812 37 Bratislava, Slovak Republic


In situ prepared magnesium salts of ethyl malonate react with 5-X-2-furoyl chlorides (X = Br, NO2, C6H5S and C6H5SO2) to give the corresponding ethyl 5-X-2-furoylmalonates. On treatment of these compounds with secondary amines no nucleophilic substitution of the group X in position 5 of the furan nucleus took place but, instead, amides of 5-X-2-furancarboxylic acids were isolated.