Gizolme, Marie (2007) New forniation of macrocyclic ureas. PhD thesis Chimie organique, Laboratoire de Chime organique (ENSTA / UCP-CO), EP/X p.258.
Full text not available from this repository. |
|
Alternative Locations: http://www.imprimerie.polytechnique.fr/Theses/Files/Gizolme.pdf
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.
| Item Type: | PhD Thesis (PhD) |
|---|---|
| Thesis Supervisor: | Elkaim, Laurent |
| Date: | 27 November 2007 |
| Board of examiners: | Jacques, Royer and Hugues, Bienayme and Christine, Greck and Christophe, Meyer |
| Ecole Doctorale: | ED 447 ECOLE DOCTORALE DE L'ECOLE POLYTECHNIQUE |
| Discipline: | Chimie organique |
| Collection (Fonds): | EP/X ENSTA |
| Institution: | EP/X |
| Department: | Laboratoire de Chime organique (ENSTA / UCP-CO) |
| Subjects: | 6. Chemistry, Physical Chemistry and Chemical Engineering |
| Uncontrolled Keywords: | Ugi and Passerini couplings, Smiles, Phenols, Heterocyclic thiols, Indolizines, Cycloaddition 3+2, Réctions de Ugi et Passerini, Smiles, Phénols, Mercaptans, Hétérocycles, Indolizines, Cycloaddition 3+2 |
Table of content
I. Réactions multicomposants
II. Synthèse d'indolizines
III. Couplage Ugi-Smiles des thiols aromatiques
IV. Couplage Ugi-Smiles des thiols hétérocycliques
V. couplage Passerini-Smiles
| ID Code: | 3258 |
|---|---|
| Deposited By: | Laurence Vidament |
| Deposited On: | 09 January 2008 |
Repository Staff Only: edit this item