An Attempt to Achieve Hydrated Imidazoline Ring Expansion (HIRE) of Diarene-Fused [1,4]Diazepinones Delivers Selective Dopamine D 2Receptor Ligands

Sergey Grintsevich, Alexander Sapegin, Beata Duszyńska, Andrzej J. Bojarski, Mikhail Krasavin

Research output: Contribution to journalArticlepeer-review

Abstract

Attempts to extend the hydrated imidazoline ring expansion (HIRE) strategy to a series of diarene-fused [1,4]diazepinones (earlier applied successfully to bis-pyrido substrate nevirapine) did not result in ring expansion but, rather, led to 2-aminoethyl side chain expulsion. This seeming setback (setting the limitations to the HIRE methodology substrate scope) led to the discovery of selective dopamine D2ligands with elements of structureactivity relationships.

Original languageEnglish
JournalSynthesis (Germany)
DOIs
StateE-pub ahead of print - 20 Sep 2021

Scopus subject areas

  • Catalysis
  • Organic Chemistry

Keywords

  • 2-aminoethyl side chain expulsion
  • fused imidazolinium moiety
  • hydrated imidazoline ring expansion
  • selective dopamine D ligands
  • [1,4]diazepinones

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