Collect. Czech. Chem. Commun. 1982, 47, 1738-1745

1,3-Dipolar cycloadditions of ylide of 5-nitro-2-furfurylpyridinium bromide in indolizine synthesis

Jarmila Štetinová, Miloslava Dandárová, Jaroslav Kováč, Darina Mesárošová and Ján Leško

Department of Organic Chemistry, Slovak Institute of Technology, 880 37 Bratislava


Substituted 3-(5-nitro-2-furyl)indolizines III-X were synthesized by 1,3-dipolar cycloaddition reaction of the ylide II, generated from 5-nitro-2-furfurylpyridinium bromide (I), with acrylonitrile, ethyl acrylate, diethyl maleate, benzalacetophenone, ethyl 3-(5-nitro-2-furyl)acrylate, (5-nitro-2-furfurylidene)acetophenone, β-nitrostyrene and dimethyl acetylenedicarboxylate. The structure of these products is discussed on the basis of their 1H NMR and mass spectra.