Simple and efficient methods of synthesis of 3,3-diarylcyclobutanone and 3,3-diarylcyclobutylamine derivatives using the TiCl4/R3N reagent system.
[reaction: see text] The iminium ions generated in situ by the oxidation of N,N-diisopropyl-N-benzylamine using iodine react with diaryl ketones in the presence of TiCl4/R3N to give the corresponding 3,3-diarylcyclobutanones in moderate to good yields (49-86%). The 3,3-diarylcyclobutanone iminium ions formed in this transformation was reduced in situ with B2H6 to produce the corresponding 3,3-diarylcyclobutylamines (52-79% yields), a class of compounds with potential antidepressant activity. In addition, a series of N,N-dimethyl-3,3-diarylcyclobutylamines were synthesized by the reductive amination of the corresponding 3,3-diarylcyclobutanone derivatives.
Amines↗