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.
School of Chemistry, University of Hyderabad, Central University P. O., Hyderabad-500 046, India. mpsc@uohyd.ernet.in
Mariappan
M
Periasamy
K Natarajan
KN
Jayakumar
Pandi
P
Bharathi
D000588:Amines / Q000138:chemical synthesis; D003500:Cyclization; D003503:Cyclobutanes / Q000138:chemical synthesis; D007097:Imines / Q000737:chemistry; D007202:Indicators and Reagents; D008956:Models, Chemical; D010084:Oxidation-Reduction; D014025:Titanium / Q000737:chemistry*
D000588:Amines; D003503:Cyclobutanes; D007097:Imines; D007202:Indicators and Reagents; C025096:titanium tetrachloride; D014025:Titanium