Intramolecular cyclization of O-(3,5-dinitrophenyl) and O-(3-amino-5-nitrophenyl) ketoximes, products of transformations of 1,3,5-trinitrobenzene. The synthesis of nitrobenzo[b]furans and 4-hydroxynitroindoles

O-(3,5-Dinitrophenyl) ketoximes obtained in the reactions of ketoximes with 1,3,5-trinitrobenzene undergo acid-catalyzed cyclization into 2-substituted or 2,3-disubstituted 4,6-dinitrobenzob]furans. In analogous cyclization, products of selective reduction of a nitro group in O-(3,5-dinitrophenyl) ketoximes unexpectedly yield, along with 6-amino-4-nitrobenzofurans, 4-hydroxy-6-nitroindoles. The 4-NO₂ group is displaced from 4,6-dinitrobenzob]furans in reactions with thiols in the presence of K₂CO₃. Conditions for nitration and sulfochlorination of 4,6-dinitrobenzob]furans in position 3 were found. Condensation of a 2-methyl derivative with dimethylformamide acetal was accomplished. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 984–991, May, 2007.