Transition-Metal-Free Reverse Reactivity of (2-Alkynyl)-Arylaldimines: Assembly of Functionalized Amino-Indinones

Kapil Mohan Saini, Rakesh K. Saunthwal, Sushmita, Akhilesh K. Verma*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

1 Citation (Scopus)

Abstract

Transition-metal-free regioselective synthesis of functionalized amino-indenones by the reaction of ortho-alkynylaldehydes with a broad range of primary amines by intramolecular cyclization has been described. The designed reaction proceeds through KOH-mediated Prins-type cyclization and DMSO-promoted oxidation of the cyclopent-2-en-1-one system. The proposed mechanism and role of solvent were well supported by control experiments. For the first time, we have disclosed the reverse reactivity of (2-alkynyl)-arylaldimines in a super basic system.

Original languageEnglish
Pages (from-to)1017-1021
Number of pages5
JournalChemistry - A European Journal
Volume26
Issue number5
DOIs
Publication statusPublished - 16 Jan 2020

Keywords

  • amino-indinones
  • ortho-alkynyl aldehyde
  • primary amines
  • regioselectivity
  • transition-metal-free reactions

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