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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)

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