1,2- vs 1,4-Addition of acylbenzotriazoles to alpha,beta-unsaturated aldehydes and ketones. A novel route to 3-alkyl-4,6-diaryl-3,4-dihydropyran-2-ones.
Lithiation of aliphatic 1-acylbenzotriazoles with subsequent reaction with alpha,beta-unsaturated ketones and aldehydes affords either 3,4,6-trisubstituted 3,4-dihydropyran-2-ones or 1,3-dienes depending on the carbonyl reagent used. Substituent effects on product yield and isomer ratio are discussed.
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
Denisko
Olga V
OV