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

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Author(s)
Krasavin, Mikhail
Parchinsky, Vadislav
Griffith University Author(s)
Year published
2010
Metadata
Show full item recordAbstract
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.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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Journal Title
Tetrahedron Letters
Volume
51
Issue
43
Copyright Statement
© 2011 Elsevier. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal's website for access to the definitive, published version.
Subject
Organic Chemical Synthesis
Medicinal and Biomolecular Chemistry
Organic Chemistry