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Synthesis 2000; 2000(10): 1474-1478
DOI: 10.1055/s-2000-7120
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Synthesis of 2-R-4,6-Dinitro-2H-indazoles from 2,4,6-Trinitrotoluene

Alexander M. Kuvshinov* , Valentina I. Gulevskaya, Vladimir V. Rozhkov, Svyatoslav A. Shevelev
  • *N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp., 47, 117913, Moscow, Russia; Fax + 7(095)1 35 53 28; E-mail: shevelev@cacr.ioc.ac.ru
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Publication Date:
31 December 2000 (online)

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An efficient synthesis of 2-R-4,6-dinitro-2H-indazoles (R = aryl or substituted amine) from 2,4,6-trinitrotoluene was elaborated. The proposed method includes formation of C-(2,4,6-trinitrophenyl)-N-R-azomethines 1 (a - g) from TNT or the product of its transformation 2,4,6-trinitrobenzaldehyde (TNBA) with the further regiospecific substitution of the ortho-nitro group in 1 (a - g) by the azido group under the action of NaN3. Thermolysis of the azides 2 (a - g) gives previously unknown 2-R-4,6-dinitro-2H-indazoles 3 (a - g) in high yields.

2,4,6-trinitrotoluene - 2,4,6-trinitrobenzaldehyde - azomethines - aromatic nucleophilic substitution - aromatic azides - 2-R-4,6-dinitro-2H-indazoles

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