Facile regiodivergent synthesis of spiro pyrrole-substituted pseudothiohydantoins and thiohydantoins via reaction of [e]-fused 1H-pyrrole-2,3-diones with thiourea
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Issue Date
2019-11-27Author
Kobelev, Aleksandr I.
Tretyakov, Nikita A.
Stepanova, Ekaterina E.
Dmitriev, Maksim V.
Rubin, Michael
Maslivets, Andrey N.
Publisher
Beilstein-Institut
Type
Article
Article Version
Scholarly/refereed, publisher version
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A highly divergent synthesis of regioisomeric thiohydantoins and pseudothiohydantoins spiro-fused to a pharmacologically valuable pyrrole-2-one fragment involving the reaction of [e]-fused 1H-pyrrole-2,3-diones with thioureas was developed. The obtained spiro pseudothiohydantoin derivatives were found to undergo a pseudothiohydantoin–thiohydantoin rearrangement. The reactions were shown to proceed under catalyst-free conditions in good yields, and the products were isolated without applying preparative chromatography methods.
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This work is licensed under a Creative Commons Attribution 4.0 International License.
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Citation
Kobelev, A. I., Tretyakov, N. A., Stepanova, E. E., Dmitriev, M. V., Rubin, M., & Maslivets, A. N. (2019). Facile regiodivergent synthesis of spiro pyrrole-substituted pseudothiohydantoins and thiohydantoins via reaction of [e]-fused 1H-pyrrole-2,3-diones with thiourea. Beilstein journal of organic chemistry, 15, 2864–2871. https://doi.org/10.3762/bjoc.15.280
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