Trifluoromethyl-substituted Δ3-imidazolines: Synthesis and reactivity

✍ Scribed by Christopher W. Derstine; David N. Smith; John A. Katzenellenbogen

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 234 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00934-9

✦ Synopsis

We describe the preparation of various 4-trifluoromethyl-substituted A3-imidazolines, which are precursors to amino acid-derived trifluoromethyl ketones. The imidazolines are prepared from ot-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.