Abstract
The reaction of hydroxylamine and steroid obtained by the condensation of 16α,17α-epoxypregn-5-en-20-one with DMF dimethyl acetal proceeded through the involvement of the epoxide fragment and led to the formation of 3β-hydroxy-4′-hydroxylaminoandrost-5-eno[16,17-b]pyridine l′-N-oxide.
References
I. V. Zavarzin, V. V. Chertkova, I. S. Levina, E. I. Chernoburova, Russ. Chem. Rev., 2011, 80, 661; DOI: https://doi.org/10.1070/RC2011v080n07ABEH004169.
S. Ke, Mini Rev. Med. Chem., 2018, 18, 745; DOI: 1.2174/1389557517666171003103245.
M. Ibrahim-Ouali, F. Dumur, ARKIVOC, 2020, 2019, 304; DOI: https://doi.org/10.24820/ark.5550190.p010.988.
A. Iqbal, T. Siddiqui, Steroids, 2021, 170, 108827; DOI: https://doi.org/10.1016/j.steroids.2021.108827.
A. V. Komkov, A. O. Chizhov, A. S. Shashkov, I. V. Zavarzin, Russ. Chem. Bull., 2018, 67, 1088; DOI: https://doi.org/10.1007/s11172-018-2185-5.
A. G. Malykh, A. R. Pavlov, A. V. Komkov, Y. A. Volkova, L. G. Menchikov, I. V. Zavarzin, Mendeleev Commun., 2021, 31, 667; DOI: https://doi.org/10.1016/j.mencom.2021.09.025.
A. V. Komkov, L. G. Menchikov, A. S. Dmitrenok, A. M. Scherbakov, D. I. Salnikova, I. S. Levina, I. V. Zavarzin, Chem. Heterocycl. Compd., 2023, 59, 554; DOI: https://doi.org/10.1007/s10593-023-03233-8.
A. V. Komkov, L. G. Menchikov, A. S. Dmitrenok, I. V. Zavarzin, Chem. Heterocycl. Compd., 2023, 59, 614.
K. Hirota, Y. Nakazawa, Y. Kitade, H. Sajiki, Heterocycles, 1998, 47, 871; DOI: https://doi.org/10.3987/COM-97-S(N)97.
Y.-Z. Ling, J.-S. Li, Y. Liu, K. Kato, G. T. Klus, A. Brodie, J. Med. Chem., 1997, 40, 3297; DOI: https://doi.org/10.1021/jm970337k.
Funding
The work was carried out in accordance with the research plan of the Institute of Organic Chemistry of the RAS.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Animal Testing and Ethics
No human or animal subjects were used in this research.
Conflict of Interest
The authors declare no competing interests.
Additional information
Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 70th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 73, No. 2, pp. 458–460, February, 2024.
Rights and permissions
About this article
Cite this article
Komkov, A.V., Menchikov, L.G., Dmitrenok, A.S. et al. Unusual reaction of 16α,17α-epoxypregn-5-en-20-one derivative with hydroxylamine. Russ Chem Bull 73, 458–460 (2024). https://doi.org/10.1007/s11172-024-4153-6
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-024-4153-6