Thiophene-containing products of the Ugi reaction in an oxidation-triggered IMDA/aromatization cascade: a simple access to 3-oxoisoindolines |
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| Authors: | Mikhail Krasavin Vadislav Parchinsky |
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| Institution: | a Science and Education Center ‘Innovative Research’, Yaroslavl State Pedagogical University, 150000, Russia
b Chemical Diversity Research Institute, 2a Rabochaya St., Moscow Reg., Khimki 141400, Russia |
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| Abstract: | A novel approach to skeletally diverse 3-oxoisoindolines has been developed which includes preparation of Ugi adducts containing thiophene and fumaric acid residues. When treated with excess m-CPBA at room temperature, these precursors undergo a simple oxidative cycloaddition/aromatization transformation and the corresponding 3-oxoisoindoline products are isolated in fair chemical yield over two steps. The second step is thought to include S-oxidation/IMDA/S-oxidation/SO2 extrusion/aromatization events. |
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| Keywords: | Isocyanide-based multicomponent reactions Post-Ugi transformation Intramolecular Diels-Alder reaction Oxidative cycloaddition Thiophene oxidation Sulfur dioxide extrusion Aromatization |
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