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A new Mumm-type rearrangement with dithiocarbamates via isocyanide-based multicomponent reaction under ultrasound irradiation: synthesis of polysubstituted pyrrolidine compounds

Matloubi Moghaddam, F ; Sharif University of Technology | 2020

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  1. Type of Document: Article
  2. DOI: 10.1039/d0nj00691b
  3. Publisher: Royal Society of Chemistry , 2020
  4. Abstract:
  5. A novel and efficient multicomponent reaction for the synthesis of polysubstituted pyrrolidine derivatives is described under catalyst-free conditions using ultrasonic irradiation. The reactions were performed via a one-pot four-component condensation of secondary amines, carbon disulfide, isocyanides, and gem-dicyano olefins at room temperature to afford polysubstituted pyrrolidines diastereoselectively in 56-96% yields. This is the first report of a Mumm-type rearrangement with dithiocarbamates followed by intramolecular cyclization, which leads to the preparation of the key structure of pyrrolidine. This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique
  6. Keywords:
  7. Amines ; Cyanides ; Cyclization ; Irradiation ; Sulfur compounds ; Ultrasonics ; Dithiocarbamates ; Intramolecular cyclizations ; Key structures ; Multi-component reactions ; Polysubstituted pyrrolidines ; Pyrrolidine derivatives ; Secondary amines ; Ultrasound irradiation ; Synthesis (chemical) ; Alkene ; Dithiocarbamic acid ; Pyrrolidine derivative ; Carbon nuclear magnetic resonance ; Catalyst ; Diastereoisomer ; Electron ; Michael addition ; Polymerization ; Priority journal ; Proton nuclear magnetic resonance ; Reaction analysis ; Room temperature ; Stereoselectivity ; Substitution reaction ; Synthesis ; Ultrasound
  8. Source: New Journal of Chemistry ; Volume 44, Issue 23 , May , 2020 , Pages 9699-9702
  9. URL: https://pubs.rsc.org/en/content/articlelanding/2020/nj/d0nj00691b#!divAbstract