Synthesis of 3-R-2-aryl-4,6-dinitroindoles and specific features of their reactions with anionic nucleophiles

Reaction of different anionic S-nucleophiles with 3-R-2-aryl-4,6-dinitroindoles led to a regiospecific nucleophilic substitution of the nitro group in position 4 with 6-NO₂ group remaining intact. The representatives of some peri-annulated polycyclic systems were synthesized on the basis of the substitution products. Dedicated to Academician V. A. Tartakovsky in honor of his 75th anniversary. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1543–1547, August, 2007.     

1,3‐Dipolar cycloaddition of unstabilized N‐methyl azomethine ylide to nitrobenzene annelated with azoles

The 1,3‐dipolar cycloaddition of unstabilized N‐methyl azomethine ylide to mononitro benzazoles was studied. Depending on the nature of substituents and annelated azoles, the reaction affords previously unknown isoindole fused heterocyclic systems. The reactivity of the cycloadducts was examined. J. Heterocyclic Chem., (2011).     

Synthesis and oxidative cyclization of 7-amino-3-R-4,6-dinitrobenzo[d]isoxazoles

A method was developed for the selective amination of 3-R-4,6-dinitrobenzo[d]isoxazoles at position 7 via the oxidative nucleophilic substitution of hydrogen. The resulting nitroamines were used to synthesize representatives of the previously unknown tricyclic heteroaromatic system, viz., isoxazolo[5,4-e]benzofuroxan.     

Functionalization of 4,6-dinitro-2-phenylindole at position 7

Transformation of the amino group in 7-amino-1-methyl-4,6-dinitro-2-phenylindole afforded a number of new 7-R-4,6-dinitroindoles and a first representative of a novel tricyclic heteroaromatic system of [1,2,5]oxadiazolo[4,3-g]indole. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1508–1511, July, 2008.     

Synthesis of 3-R-1,5-dinitro-3-azabicyclo[3.3.1]nonanes fused to azoles

3-R-1,5-Dinitro-3-azabicyclo[3.3.1]nonanes fused to the pyrazole, thiazole, and triazole rings were synthesized by reductive cyclization of meta-dinitrobenzazoles.