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Réactions multicomposants et isonitriles.

Abstract : Much work was published over the twenty last years about Passerini and Ugi couplings, isocyanide based multicomponent reactions. These reactions are of particular interest since they provide diversified and complex products in one single step, with good yields. We first developed a new method to prepare indolizines, implying a Ugi reaction and a [3+2] cycloaddition of pyridinium salt. This is the key step of a domino reaction Sonogashira/cycloaddition/oxidation. Heterocyclic systems of biological interest are obtained with high structural complexity. A novel Ugi-type process involving phenols instead of carboxylic acids was disclosed recently in the laboratory. In this work, we studied Passerini-type couplings of phenols. O-nitrophenol, as well as heterocyclic phenols, provided the expected aryloxyamides. The key step of the reaction lies in an irreversible Smiles rearrangement of intermediate phenoxyimidate adducts. Then we tested the behaviour of thiols in the Ugi-Smiles sequence. Various thioamides were formed easily. The use of heterocyclic rings of different sizes allowed the preparation of new compounds.
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Submitted on : Tuesday, July 27, 2010 - 3:21:48 PM
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  • HAL Id : pastel-00003258, version 1



Marie Gizolme. Réactions multicomposants et isonitriles.. Chimie. Ecole Polytechnique X, 2007. Français. ⟨pastel-00003258⟩



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