110315-00-9Relevant articles and documents
5-Oxazolones, II 2,4-Diaryl-4-(2,4-dinitroaryl)-5(4H)-oxazolones: Synthesis and Acid-Catalyzed Transformation into 1-Hydroxy-1H-indazole Derivatives
D'Anello, Matteo,Erba, Emanuela,Gelmi, Maria Luisa,Pocar, Donato
, p. 67 - 74 (2007/10/02)
2,4-Diaryl-4-(2,4-dinitroaryl)-5(4 H)-oxazolones 2 were prepared by arylation of the corresponding 5(4H)-oxazolones 1 under phase-transfer conditions with the corresponding 1-halo-2,4-dinitrobenzenes. 2,4-Diaryl-4-(3,5-dinitro-2-pyridyl)-5(4H)-oxazolones 5 were obtained similarly from the corresponding 1 and 2-chloro-3,5-dinitropyridine.On reaction with methanol and p-toluenesulfonic acid , oxazolones 2 rearranged to the corresponding 1-hydroxy-1H-indazole derivatives 8.Under the same conditions oxazolones 5 afforded a mixture of the correspondingly substituted 1H-pyrazolopyridines 7 and substituted imidazopyridines 12.In all cases the solvolysis reaction, yielding substituted glycine esters 9 and 11, was competitive with the rearrangement.Reaction path are discussed.