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Unexpected formation of novel pyrrole derivatives by the reaction of thioamide with dimethyl acetylenedicarboxylate
Authors:Hirofumi Nakano  Tomoaki IshibashiToshihiko Sawada
Institution:Department of Chemistry, Aichi University of Education, Igaya, Kariya, Aichi 448-8542, Japan
Abstract:The reaction of thioamides with DMAD gave the pyrrole derivatives in good yield and the thiophene derivatives as a byproduct. These were formed by 1,3-dipolar cycloaddition of themodynamicaly stable azomethine ylide or less stable thiocarbonyl ylide with DMAD, followed by elimination of thioaldehyde or imine derivatives.
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