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Elsevier, Tetrahedron Letters, 43(51), p. 5657-5661

DOI: 10.1016/j.tetlet.2010.07.135

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Thiophene-containing products of the Ugi reaction in an oxidation-triggered IMDA/aromatization cascade: a simple access to 3-oxoisoindolines

Journal article published in 2010 by Mikhail Krasavin ORCID, Vadislav Parchinsky
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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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.