Syntheses of gem-dinitro heterocyclic compounds, their ring-opening reactions and transformations into indoles, indazoles and benzoxazinones

Article abstract of DOI:10.1016/S0040-4020(99)00570-0

The synthesis of some novel 3,3,5,7-tetranitrooxindoles and 4,4- dinitropyrazol-5-ones and their behaviour towards various nucleophiles and electrophiles are reported. Reactions with hydroxide ions or secondary amines produced salts of e.g. 2-amino-3,5-dinitrophenyldinitromethane, which subsequently could be further transformed into indazoles, indoles or benzoxazinones depending upon substrate and conditions used. Mechanisms are discussed.