Base Mediated Reactions in Solid-Liquid Media. A 1,3-Dipolar Cycloaddition Route to Pyrrolines and Pyrroles from Imino Chlorosulfides.

Article abstract of DOI:10.1016/S0040-4039(00)60030-8

Nitrile ylides, generated in basic conditions (HCl abstraction) from N- and N-imino chlorosulfides, undergo 1,3-dipolar cycloadditions with electron-deficient dipolarophiles to produce pyrroles and pyrrolines.Heterogeneous media are found to furnish the best conditions for these reactions.One pyrrole can also be prepared from methyl N- chlorothioimidate and dimethyl acetylenedicarboxylate on alumina-potassium fluoride mixture as solid support, under microwave irradiation. Key words: Imino chlorosulfides; alumina-dispersed potassium fluoride and potassium hydroxide; 1,3-dipolar cycloaddition; pyrroles.