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Heterocyclic analogs of prostaglandins: III. Synthesis of 10-oxa-13-aza, 11-oxa-13-aza, and 9-oxa-7-aza prostanoids from 3-acyl-and 3-(3-arylprop-2-enoyl)furan-2,4-diones

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Abstract

A number of new 10-oxa-13-aza, 11-oxa-13-aza, and 9-oxa-7-aza prostanoids belonging to the B series were synthesized on the basis of 3-acyl-and 3-(3-arylprop-2-enoyl)furan-2,4(3H,5H)-diones. The scheme of synthesis includes selective hydrogenation of the exocyclic carbonyl group and reduction of the conjugated double bond in the acyl fragment of 3-acyl-and 3-(3-arylprop-2-enoyl)furan-2,4(3H,5H)-diones to obtain 3-alkyl-and 3-(3-arylpropyl)furan-2,4(3H,5H)-diones, transformation of the latter into the corresponding regioisomeric enol ethers via regioselective O-alkylation, and treatment of the enol ethers with primary aliphatic amines.

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, Minsk, 220141, Belarus

    F. S. Pashkovskii, E. M. Shchukina, M. G. Gribovskii & F. A. Lakhvich

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  1. F. S. Pashkovskii
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  2. E. M. Shchukina
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  3. M. G. Gribovskii
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  4. F. A. Lakhvich
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Additional information

Original Russian Text © F.S. Pashkovskii, E.M. Shchukina, M.G. Gribovskii, F.A. Lakhvich, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 4, pp. 545–559.

For communication II, see [1].

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Pashkovskii, F.S., Shchukina, E.M., Gribovskii, M.G. et al. Heterocyclic analogs of prostaglandins: III. Synthesis of 10-oxa-13-aza, 11-oxa-13-aza, and 9-oxa-7-aza prostanoids from 3-acyl-and 3-(3-arylprop-2-enoyl)furan-2,4-diones. Russ J Org Chem 42, 527–540 (2006). https://doi.org/10.1134/S1070428006040087

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  • DOI: https://doi.org/10.1134/S1070428006040087

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