Skip to Main content Skip to Navigation

Nouvelles applications de la réaction de Passerini dans des réactions de type Friedel-Crafts et Tsuji-Trost.

Abstract : The development of rapid and efficient syntheses of complex molecules from simple starting substrates using a minimum of steps is a real challenge of contemporary organic chemistry. In this context, multicomponent reactions, thanks to their ability to create several one-step bonds, offer a high efficiency in synthesizing structures of great molecular complexity. Moreover, organometallic catalysis has developed considerably in recent years, becoming a tool of choice for the formation of carbon-carbon bonds. The Tsuji-Trost reaction is specially well known in this field.In this thesis, the discovery of the original post-condensations from the adducts obtained by multicomponent reactions involving isonitrile is the major axis of our research. These reactions allow efficient access to a wide range of heterocyclic compounds.First, we have developed a new efficient pathway for the synthesis of indolylacetamides via the Passerini/Friedel-Crafts cascade from the Passerini adducts and indole in the presence of a Lewis acid. A one-pot version of this cascade has been also developed.Furthermore, we have exploited the reactivity of N-monosubstituted hydrazones as 1,3-bis-nucleophile in order to prepare various 2-pyrazoline derivatives via a pallado-catalyzed Tsuji-Trost/Cyclisation cascade from the Passerini adducts or Phosphonates. In order to prepare enantioselectively enriched 2-pyrazolines, the enantioselective version of this cascade was also realized from the Passerini adduct.Finally, the development of a new Tsuji-Trost/Cyclization cascade from the Passerini adducts and the allyl methyl carbonate provide straight fast and efficient access to oxazolidine-2,4-diones heterocyclic units by exploiting the carbon dioxide generated in situ.
Document type :
Complete list of metadata
Contributor : ABES STAR :  Contact
Submitted on : Monday, July 10, 2017 - 11:20:51 AM
Last modification on : Friday, January 7, 2022 - 3:47:21 AM
Long-term archiving on: : Thursday, January 25, 2018 - 12:05:31 AM


Version validated by the jury (STAR)


  • HAL Id : tel-01531785, version 2


Elhachemia Elmamouni. Nouvelles applications de la réaction de Passerini dans des réactions de type Friedel-Crafts et Tsuji-Trost.. Chimie organique. Université Paris Saclay (COmUE), 2017. Français. ⟨NNT : 2017SACLX011⟩. ⟨tel-01531785v2⟩



Record views


Files downloads