Abstract
The cyclization of the piperidine-2,3-dione 3-hydrazone obtained from the three-ring steroid BCD fragment proceeds with the primary formation of a p-substitution product. According to the PMR spectral data, the ratio of the para and ortho isomers is 3.3∶2.
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V. I. Sladkov, V. F. Shner, O. S. Anisimova, L. M. Alekseeva, L. I. Lisitsa, A. I. Terekhina, and N. N. Suvorov, Zh. Org. Khim., 10, 1290 (1974).
B. Robinson, Chem. Rev., 69, 227 (1969).
Yu. P. Kitaev and B. I. Buzykin, Hydrazones [in Russian], Nauka, Moscow (1974), p. 235.
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The authors thank K. F. Turchin and T. Ya. Filipenko for recording and interpreting the PMR spectra.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1087–1089, August, 1977.
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Sladkov, V.I., Anisimova, O.S. & Suvorov, N.N. Investigation of the direction of the Fischer cyclization of arylhydrazones that are derivatives of hexahydrobenz[e]indene cyclization of a piperidine-2,3-dione 3-hydrazone. Chem Heterocycl Compd 13, 875–877 (1977). https://doi.org/10.1007/BF00488914
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DOI: https://doi.org/10.1007/BF00488914