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Transformed steroids. 160. Reaction of 20,20-dimethoxy-16α,17α-epoxypregn-5-ene-3β, 21-diol-20-one with pyridine thiocyanate and carbethoxyhydrazine

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Conclusion

The reaction of 20,20-dimethoxy-16α,17α-epoxypregn-5-ene-3β,21-diol-20-one with pyridine thiocyanate in the presence of carbethoxyhydrazine proceeds by two competing paths: cisopening of the oxide ring by a -SCN ion at the C17 atom, and substitution of one of the methoxyl groups by -NCS ion. As a result 2′,20-dicarbethoxyhydrazones of pregn-5-ene-3β,21-diol-20-one-[17α,16α-d]-1′,3′-oxathiolan-2′-one and 20-methoxy-16α,17α-epoxypregn-5-ene-3β-ol-[20,21-d]-1′,3′-oxazolidine-2′-thione are formed.

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Authors and Affiliations

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

    A. V. Kamernitskii & A. M. Turuta

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  1. A. V. Kamernitskii
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  2. A. M. Turuta
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 911–914, April, 1987.

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Kamernitskii, A.V., Turuta, A.M. Transformed steroids. 160. Reaction of 20,20-dimethoxy-16α,17α-epoxypregn-5-ene-3β, 21-diol-20-one with pyridine thiocyanate and carbethoxyhydrazine. Russ Chem Bull 36, 837–840 (1987). https://doi.org/10.1007/BF00962334

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  • DOI: https://doi.org/10.1007/BF00962334

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