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Reactions of Methyl 2-Formylfuro[3,2-b]pyrrole-5-carboxylates

A. Krutošíková and M. Dandárová

Department of Organic Chemistry, Faculty of Chemical Technology, Slovak Technical University, SK-812 31 Bratislava

 

Abstract: A series of 5-methoxycarbonyl-4-R-furo[3,2-b]pyrrole-2-carbaldehyde 2,6-R1,R2-phenylhydrazones and 5-methoxycarbonyl-4-R-furo[3,2-b]pyrrole N,N-dimethylhydrazones were prepared from methyl 2-formyl-4-R-furo[3,2-b]pyrrole-5-carboxylates. By the reaction of the latter with hydroxylammonium chloride in acetic anhydride in the presence of pyridine methyl 2-cyano-4-R-furo[3,2-b]pyrrole-5-carboxylates were obtained. The reaction of these compounds with sodium azide and ammonium chloride in dimethylformamide led to methyl 2-(5'-tetrazolyl)-4-R-furo[3,2-b]pyrrole 5-carboxylates. The reaction of methyl 2-formyl-4-R-furo[3,2-b]pyrrole-5-carboxylates with malononitrile afforded 5-methoxycarbonyl-4-R-furo [3,2-b]pyrrol-2-ylidenemalononitriles, with methyl cyanoacetate methyl 2-cyano-3-[(5-methoxycarbonyl-4-R-furo[3,2-b]pyrrol)-2-yl]propenoates and with 2-furylacetonitrile 2-(2-furyl)-3-[(5-methoxycarbonyl-4-R-furo[3,2-b]pyrrol)-2-yl] acrylonitriles.

Full paper in Portable Document Format: 502a72.pdf

 

Chemical Papers 50 (2) 72–76 (1996)

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