| Abstract: | Organic Syntheses Based on 2-Oxoglutaric Acid. III. Synthesis and Reactions of Dimethyl (E)-2-oxoglutaconate Dimethyl (E)-2-oxoglutaconate 1 obtained by dehydrobromination of dimethyl 3-bromo-2-oxoglutarate reacts with o-phenylendiamine to form the quinoxalin-2(1H)-one 2 , and with phenylhydrazine to yield the 4,5-dihydropyrazole 3 . Furthermore, a Doebner-von Miller-type reaction affords the 8-carboxy quinoline derivative 4 . Finally, addition of bromine leads diastereoselectively to the racemate of dimethyl 3S,4R- and 3R,4S-dibromo-2-oxoglutarate 5 . |
