Studies on isocyanides: synthesis of tetrazolyl-isoindolinones via tandem Ugi four-component condensation/intramolecular amidation

The Ugi four-component condensation between methyl o-formylbenzoates 1, anilines 2a– c, isocyanides 3, and trimethylsilyl azide ( 4) afforded the expected Ugi adducts 5a– d, which were cyclized to the title compounds 6a– d upon treatment with sodium ethoxide in ethanol. Starting from aralkyl- or alk...

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Bibliographic Details
Published in:Tetrahedron letters 2008, Vol.49 (1), p.149-152
Main Authors: Marcos, Carlos F., Marcaccini, Stefano, Menchi, Gloria, Pepino, Roberto, Torroba, Tomás
Format: Article
Language:English
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Summary:The Ugi four-component condensation between methyl o-formylbenzoates 1, anilines 2a– c, isocyanides 3, and trimethylsilyl azide ( 4) afforded the expected Ugi adducts 5a– d, which were cyclized to the title compounds 6a– d upon treatment with sodium ethoxide in ethanol. Starting from aralkyl- or alkylamines 2d– g the Ugi adducts underwent a spontaneous cyclization to tetrazolyl-isoindolinones 6e– j.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.10.154