Organic Syntheses Based on 2-Oxoglutaric Acid. II. On the Synthesis of Heterocycles by Reactions of Dimethyl 3-bromo-2-oxoglutarate with Binucleophiles

Article abstract of DOI:10.1002/prac.19933350210

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.