(E)-3-Arylidene-4-diazopyrrolidine-2,5-diones: Preparation and Use in Rh-II-Catalyzed X-H Insertion Reactions towards Novel, Medicinally Important Michael Acceptors

Evgeny Chupakhin, Martha Gecht, Alexander Ivanov, Grigory Kantin, Dmitry Dar'in, Mikhail Krasavin

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

The use of readily available 1-aryl-3-arylidenepyrrolidine2,5-diones in high yielding direct diazo-transfer reactions and subsequent involvement of the resulting diazo compounds in Rh-II-catalyzed O-H, S-H, and N-H insertion reactions delivered 4-substituted 1-aryl-3-arylidenepyrrolidine-2,5-diones of defined regiochemistry and geometrical configuration. These products are intended to be studied as Michael acceptors capable of inhibiting thioredoxin reductase, a promising cancer target.

Original languageEnglish
Number of pages9
JournalSynthesis
DOIs
StateE-pub ahead of print - 5 Nov 2020

Keywords

  • Michael acceptors
  • pyrrolidine-2,5-diones
  • Wittig reaction
  • diazo transfer
  • rhodium(II) carbenes
  • X-H insertion
  • thioredoxin reductase inhibitors
  • MALEIMIDES
  • INHIBITORS
  • DISCOVERY
  • THIOL

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