New Building Blocks, 3,5-Dihydro-1H-thienopyrrole 2,2-Dioxides; Preparation and their Diels-Alder Reaction with Dimethyl Acetylenedicarboxylate

Article abstract of DOI:10.1016/0040-4020(94)00968-Z

New building blocks, 3,5-dihydro-1H-thieno<3,4-c>pyrrole 2,2-dioxides 3, have been prepared by the oxidation of their corresponding pyrroline derivates 4 with DDQ or Chemical MnO2.The Diels-Alder reaction of 3 with dimethyl acetylenedicarboxylate gave new types of compounds: 7-aza-2,3-dimethylenenorbornenes A, the 1:2 adducts B, 1a,3a,6,9-tetrahydrobenzindoles C, and dihydroindolosulfolene D depending on the reaction conditions and the N-substituents.The reaction of 3 with bis(tert-butylsulfonyl)acetylene was also described.