ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Substituted Vinyl Azides in the Synthesis of Condensed Nitrogen Heterocycies

A. Krutošíková, M. Dandárová, and J. Alföldi

Department of Organic Chemistry, Faculty of Chemical Technology, Slovak Technical University, SK-812 37 Bratislava

Abstract: Methyl 4H-2-R-furo[3,2-b]pyrrole-5-carboxylates were prepared by thermolysis of corresponding methyl 2-azido-3-(5-R-2-furyl)propenoates. N-Methyl and N-benzyl derivatives were obtained in phase-transfer catalysis conditions. The formylation of methyl furo[3,2-b]pyrrole-5-carboxylate and its 4-methyl or 4-benzyl derivative gave 2 formylated compounds, which by hydrolysis afforded the corresponding 2-formyl-4-R-furo[3,2-b]pyrrole-5-carboxylic acids. A number of furo[3,2-c]pyridines were prepared by reaction of the iminophosphoranes available from corresponding substituted vinyl azides and triphenylphosphine with phenyl or 3-chlorophenyl isocyanates. ¹H  and ¹³C  NMR, IR, and UV spectra are introduced.

Full paper in Portable Document Format: 484a268.pdf

Chemical Papers 48 (4) 268–273 (1994)