Collect. Czech. Chem. Commun. 1983, 48, 2682-2692

Aliphatic and aromatic 5-nitro-2-furylamines and aromatic 5-nitrofurfuryl ethers

Raul Moceloa and Jaroslav Kováčb

a Deprtment of Organic Chemistry, University of Havana, Havana, Cuba
b Department of Organic Chemistry, Slovak Institute of Technology, 812 37 Bratislava, Czechoslovakia


Tertiary 5-nitrofurylamines were prepared by a nucleophilic substitution of 5-nitro-2-furfuryl bromide (I) with aliphatic secondary amines. According to reaction conditions N-(5-nitro-2-furfuryl)-X-phenylamines or their mixture with N,N-di(5-nitro-2-furfuryl)-X-phenylamines were obtained from the reaction of I with substituted primary aromatic amines. Compound I gave with 2-aminophenol a mixture of O- and N-mono- and disubstituted derivatives, and with ethyl salicylate ethyl 2-(5-nitro-2-furfuryloxy)benzoate.