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3,6,6-trimethyl-4-oxo-1-(2-pyridyl)-4,5,6,7-tetrahydroindazole in Schmidt reaction and Beckmann rearrangement conditions for the 4-hydroxyimino derivative

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Abstract

Treatment of 3,6,6-trimethyl-4-oxo-1-(2-pyridyl)-4,5,6,7-tetrahydroindazole with sodium azide in acids gives 3,7,7-trimethyl-5-oxo-1-(2-pyridyl)-5,6,7,8-tetrahydro(4H)pyrazolo[4,3-b]azepine. Heating 1-(2-pyridyl)-3,6,6-trimethyl- and 1-phenyl-6,6-dimethyl-4-hydroxyimino-4,5,6,7-tetrahydroindazoles in polyphosphoric acid gives 1-phenyl-5,6-dimethyl- and 1-(2-pyridyl)-3,5,6-trimethyl-4-aminoindazole respectively: The reactions of the latter with 4-dimethylaminobenzaldehyde gave the 4-(4-dimethylaminobenzalamino) derivative and with 2-formyldimedone the 4-(4,4-dimethyl-2,6-dioxocyclohexylidenemethylamino) derivative.

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Authors and Affiliations

  1. Riga Technical University, LV-1658, Riga, Latvia

    L. G. Delyatitskaya, M. V. Petrova, N. N. Tonkikh & A. Ya. Strakov

  2. Latvian Institute of Organic Synthesis, LV-1006, Riga, Latvia

    S. Grinberga

Authors
  1. L. G. Delyatitskaya
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  2. M. V. Petrova
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  3. S. Grinberga
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  4. N. N. Tonkikh
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  5. A. Ya. Strakov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 830–834, June, 2000.

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Delyatitskaya, L.G., Petrova, M.V., Grinberga, S. et al. 3,6,6-trimethyl-4-oxo-1-(2-pyridyl)-4,5,6,7-tetrahydroindazole in Schmidt reaction and Beckmann rearrangement conditions for the 4-hydroxyimino derivative. Chem Heterocycl Compd 36, 728–732 (2000). https://doi.org/10.1007/BF02297683

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  • DOI: https://doi.org/10.1007/BF02297683

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