Collect. Czech. Chem. Commun. 1993, 58, 2139-2149

Synthesis and Reactions of Furo[3,2-b]pyrrole Type Aldehydes

Alžbeta Krutošíkováa, Miloslava Dandárováa and Juraj Alföldib

a Department of Organic Chemistry, Slovak Technical University, 812 37 Bratislava, Slovak Republic
b Institute of Chemistry, Slovak Academy of Sciences, 842 38 Bratislava, Slovak Republic


The synthesis of ethyl 2-formyl-4-benzylfuro[3,2-b]pyrrole-5-carboxylate (I) is described. A series of furo[3,2-b]pyrrole-2-carbaldehyde 2,6-dialkylphenylhydrazones (IIa - IIg) and dimethylhydrazones (IIIa - IIId) were prepared. By reaction of title compounds with hydroxylammonium chloride in acetic anhydride in the presence of pyridine corresponding cyano-substituted compounds (IVa - IVd) were obtained. Alkaline hydrolysis of IVa - IVd gave Va - Vb and the reaction with sodium azide and ammonium chloride in dimethylformamide led to VIa - VId. the structure of the compounds have been proved by UV, IR, 1H and 13C NMR spectra.