Synthesen auf der Basis von 2-Oxoglutarsäure. II Zur Synthese von Heterocyclen durch Reaktionen von 3-Brom-2-oxoglutarsäuredimethylester mit Binucleophilen

Organic Syntheses Based on 2-Oxoglutaric Acid. II. On the Synthesis of Heterocycles by Reactions of Dimethyl 3-bromo-2-oxoglutarate with Binucleophiles Reactions of dimethyl 3-bromo-2-oxoglutarate 2 with binucleophiles to form heterocycles proceed on two different pathways depending on the type of reactant. Thus, strong S-nucleophiles like thioureas and thiocarbohydrazide substitute initially the bromine atom and form 2-aminothiazoles 3 – 7 and the 1,3,4-thiadiazine 8 . However, o-phenylendiamines reacted to form the brominated quinoxaline-2(1H)-one derivatives 9 and 10 , resp.