Palladium-catalyzed syntheses of carbonyl containing phenethylamino pyrimidines

ORGN 157

Thomas M. Stevenson and Brett A. Crouse. Stine-Haskell Research Center, DuPont Crop Protection, P.O. Box 30, Newark, DE 19714
During the past 15 years a wide variety of heterocyclic compounds have been found which can inhibit mitochondrial electron transport at Complex I (METI). This class of chemistry has become of commercial importance for the control of both mites and fungi on a broad range of crops. We became interested in synthesis of METI compounds based on phenethylaminopyrimidines containing esters and ketones. To overcome incompatibility of the esters and ketones with the conditions used to synthesize the phenethylamines we incorporated these functional groups on the intact molecules. We were able to synthesize a wide variety of ketones and esters using carbonylation of aromatic bromides, triflates and iodides. Alternatively, we found the ketones were also available by direct Friedel-Crafts acylations on unsubstitued phenethylaminopyrimidines.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004