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Transformed steroids. 118. The geometric isomerism of 20-ethoxycarbonylhydrazones of 3β-hydroxy-16,17α-cyclopropanopregn-5-en-20-one

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Abstract

In the reaction of the 3β-acetate of 3β-hydroxy-3′H-cyclopropano[16,17α]pregn-5-en-20-one (I) with ethoxycarbonylhydrazine in AcOH at 20°C (exposure for up to 6 days), a chromatographically separable equilibrium mixture of the 20Z-ethoxycarbonylhydrazone of 3β-acetoxy-3′H-cyclopropano[16,17α]pregn-5-en-20-one (II), with mp 190–195°C, and the 20E-ethoxycarbonylhydrazone of 3β-acetoxy-3′H-cyclopropano[16,17α]pregn-5-en-20-one (III) with mp 186–193°C (ratio 2:1) is obtained. The geometric isomers obtained are distinguished by IR, PMR, and CD spectroscopy. It has been shown that the observed geometric isomerism takes place via an intermediate enehydrazine form.

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Literature cited

  1. 1.

    A. V. Kamernitskii, V. A. Krivoruchko, and I. G. Reshetova, Khim. Prir. Soedin., 208 (1980).

  2. 2.

    A. V. Kamernitskii, N. S. Pavlova-Grishikin, and A. V. Skorova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6 (1980).

  3. 3.

    A. V. Kamernitskii, A. M. Turuta, and Ngo Tkhi Mai Ani, Izv. Akad. Nauk SSSR, Ser. Khim., 924 (1980).

  4. 4.

    T. N. Deshko, A. V. Kamernitskii, G. A. Kogan, A. M. Turuta, T. K. Ustynyuk, and T. M. Fadeeva, Izv. Akad. Nauk SSSR, Ser. Khim., 2713 (1976).

  5. 5.

    Yu. P. Kitaev and B. I. Buzykin, Hydrazones [in Russian], Moscow (1974).

  6. 6.

    R. B. Boad, J. F. McGhie, M. Robinson, and D. H. R. Barton, J. Chem. Soc., Perkin Trans., I, 1242 (1975).

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Additional information

For Communication 117, see [1].

N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 530–533, July–August, 1980.

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Kamernitskii, A.V., Turuta, A.M. & Ngo Tkhi Mai An' Transformed steroids. 118. The geometric isomerism of 20-ethoxycarbonylhydrazones of 3β-hydroxy-16,17α-cyclopropanopregn-5-en-20-one. Chem Nat Compd 16, 383–386 (1980). https://doi.org/10.1007/BF00568373

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Keywords

  • Hydrazones
  • AcOH
  • Geometric Isomerism
  • HOAc
  • Furostanol