Trifluoromethyl-substituted Δ3-imidazolines: Synthesis and reactivity

Christopher W. Derstine, David N. Smith, John A. Katzenellenbogen

Research output: Contribution to journalArticlepeer-review

Abstract

We describe the preparation of various 4-trifluoromethyl-substituted Δ3-imidazolines, which are precursors to amino acid-derived trifluoromethyl ketones. The imidazolines are prepared from α-silylimines and trifluoroacetonitrile by a 3+2 cycloaddition, and they can be hydrolyzed in weak acid to trifluoromethyl ketones. Additionally, we have identified several ring-opened compounds which result from treatment of the imidazolines with acid or base. Attempts to alkylate the imidazolines led to ring-opened products, so that the alkylation sequence ultimately produced N-alkylated amino acid-derived trifluoromethyl ketones.

Original languageEnglish (US)
Pages (from-to)4359-4362
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number25
DOIs
StatePublished - Jun 23 1997

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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