Aldazines in the Castagnoli-Cushman Reaction

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4 Scopus citations

Abstract

Aldazines were employed in the Castagnoli-Cushman reaction of homophthalic anhydride for the first time. The reaction proved to be distinctly diastereoselective when conducted at room temperature in acetonitrile, yielding predominantly the kinetic cis -configured adduct as a racemate. Thermodynamically more stable trans -configuration could be attained either via heating the cis -configured product in DMSO or via the action of a base (imidazole) in the course of CDI-promoted esterification or amidation of the carboxylic acid function in the initial adducts. Further manipulation of the remaining N -acylhydrazone moiety in the latter led to N -alkyl- or fully unprotected N -aminolactams.

Original languageEnglish
Pages (from-to)2076-2086
Number of pages11
JournalSynthesis (Germany)
Volume50
Issue number10
DOIs
StatePublished - 17 May 2018

Scopus subject areas

  • Catalysis
  • Organic Chemistry

Keywords

  • aldazines
  • Castagnoli-Cushman reaction
  • homophthalic anhydride
  • hydrazone cleavage
  • hydrazone reduction
  • Naminolactams
  • non-symmetrical
  • symmetrical

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