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Réactions multicomposant à base des isonitriles

Abstract : The isocyanide based multicomponent reactions (I-MCRs) with subsequent post-condensation transformations constitute extremely powerful synthetic tools for the preparation of structurally diverse complex molecules with novel properties.In this context, we first investigated the extension of Ugi-Smiles coupling to purines, by using 6-mercaptopurine as coupling partner. This methodology allows direct access to adenine derivatives in moderate to good yields starting from readily available precursors.Then, we demonstrated that Ugi adducts derived from aromatic aldehydes may be converted to pyrrolines via addition of Michael acceptors under microwave irradiation. The reaction may proceed via unusual formation of azomethine ylides followed by a [3+2] cycloaddition using Michael acceptors.Finally, we described that the Passerini adducts of cinnamaldehyde and analogues may be efficiently converted into α-ketoamides when heated with a base under microwave conditions.
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Submitted on : Wednesday, January 10, 2018 - 11:57:52 AM
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  • HAL Id : tel-01679887, version 1


Abdelbari Ben Abdessalem. Réactions multicomposant à base des isonitriles. Chimie organique. Université Paris Saclay (COmUE); Faculté des sciences de Bizerte (Tunisie), 2016. Français. ⟨NNT : 2016SACLY024⟩. ⟨tel-01679887⟩



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