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Transformed Steroids

Communication 54. Isomerization of steroidal 20-azoolefins to hydrazones of enols and synthesis of [16,17-c]arylpyrazoles of androstane series

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The reaction of 16α, 17α-epoxy-20-keto-steroids with arylhydrazines in the presence of a small amount of acid leads to the formation of 17(20)-20-arylazo-160α-hydroxy-steroids.

  2. 2.

    The treatment of arylazoolefins with acids under drastic conditions gives steroidal [16,17-c]-3′-aryl-5′-methylpyrazoles, which are evidently formed as the result of prior isomerization to the hydrazoneenol structure.

  3. 3.

    The azoolefinic structure is not an intermediate in the cis-opening of the hydrazones of oxides.

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Literature cited

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    A. A. Akhrem, A. V. Kamernitskii, A. V. Skorova & N. S. Pavlova-Grishina

Authors
  1. A. A. Akhrem
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  2. A. V. Kamernitskii
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  3. A. V. Skorova
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  4. N. S. Pavlova-Grishina
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Additional information

See [1] for Communication 53.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 901–906, April, 1973.

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Akhrem, A.A., Kamernitskii, A.V., Skorova, A.V. et al. Transformed Steroids. Russ Chem Bull 22, 869–873 (1973). https://doi.org/10.1007/BF00857072

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  • DOI: https://doi.org/10.1007/BF00857072

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