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Regiospecificity of nucleophilic substitution in 4,6-dinitro-1-phenyl-1H-indazole

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Abstract

The reactions of 4,6-dinitro-1-phenyl-1H-indazole with anionic nucleophiles RS– and N3 – lead to the regiospecific replacement of the nitro group at position 4. The reaction with N2H4·H2O + FeCl3 also results in reduction of only the 4-NO2 group. Based on this fact, a procedure was developed for the preparation of previously unknown 3-unsubstituted 4-X-6-nitro-1-phenyl-1H-indazoles (X is a residue of a nucleophile or NH2). Comparison of the data on the selective nucleophilic substitution (4-NO2 group) in 3-Z-1-aryl-4,6-dinitro-1H-indazoles shows that in the case of Z = H, the regiospecificity of substitution is determined by the electronic effect of the annelated pyrazole ring.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. M. Starosotnikov, A. V. Lobach, V. V. Kachala & S. A. Shevelev

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  1. A. M. Starosotnikov
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  2. A. V. Lobach
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  3. V. V. Kachala
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  4. S. A. Shevelev
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Starosotnikov, A.M., Lobach, A.V., Kachala, V.V. et al. Regiospecificity of nucleophilic substitution in 4,6-dinitro-1-phenyl-1H-indazole. Russian Chemical Bulletin 53, 584–587 (2004). https://doi.org/10.1023/B:RUCB.0000035642.41056.81

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  • DOI: https://doi.org/10.1023/B:RUCB.0000035642.41056.81

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