Recherches en série hétérocyclique. XXIX. Sur des voies d'accès à des thiéno, sélénolo, furo et pyrrolopyrroles

Abstract

The reaction of ethyl azidoacetate with the monoaldehydes of furan, thiophene and seleno-phene yields furo-, thieno-, and selenolo[2,3-b]- and [3,2-b]pyrroles. Only pyrrolo[2,3-b]pyrrole could be prepared by this route using ethyl 4-formylpyrrole-2-carboxylate as the substrate. The thieno- and selenolo[3,2-b]pyrroles also could be obtained by the action of ethyl bromoacetate on 3-acetamidothiophene-2-aldehyde, or the corresponding selenolo compound, followed by cyclization of the N-substituted acetamide products.The nmr, uv, and mass spectra are reeorded for the various products described. [Journal translation]