Progress toward the synthesis of trialkylsiloxy protected aminodihydropyridinones from 1-amino-3-trialkylsiloxy-1,3-butadiene and imine

ORGN 546

Robert V O'Brien III, obri1371@seattleu.edu, Peter J. Alaimo, alaimop@seattleu.edu, Jamie O'Brien, garciaj@seattleu.edu, Sarah Slauson, slausons@seattleu.edu, Adam Johnson, john2250@seattleu.edu, and Lorien Wallace, wallacel@seattleu.edu. Department of Chemistry, Seattle University, 901 12th Avenue, Seattle, WA 98122
Dihydropyridinones have a range of biological activity, and are therefore of potential therapeutic value. 1-amino-3-(tert-butyldimethylsiloxy)-1,3-butadienes are useful substrates for synthesis of dihydropyridinones due to the ease of their synthesis as well as their high reactivity. The reaction of 1-pyrollidinyl-3-(tert-butyldimethylsiloxy)-1,3-butadiene with N-benzylideneaniline using a variety of solvent/catalyst combinations was studied, and it was determined by GC/MS that the product of this reaction was the TBDMS protected pyrollidinyldihydropyridinone cycloadduct, with yields ranging from 40-80% (as determined by GC/FID). This product has two important features: the amino group was not eliminated after cyclization and the product contains a TBDMS protected enol. These features may allow for further synthetic steps such as selective deprotection of the enol, followed by subsequent addition at the resulting keto group while preserving the amino group. The isolation and characterization of the product is in progress as well as the study of diastereoselectivity of the reaction.
 

Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006