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Facile regiodivergent synthesis of spiro pyrrole-substituted pseudothiohydantoins and thiohydantoins via reaction of [e]-fused 1H-pyrrole-2,3-diones with thiourea
Kobelev, Aleksandr I. Tretyakov, Nikita A. Stepanova, Ekaterina E. Dmitriev, Maksim V. Rubin, Michael Maslivets, Andrey N.
Kobelev, Aleksandr I.
Tretyakov, Nikita A.
Stepanova, Ekaterina E.
Dmitriev, Maksim V.
Rubin, Michael
Maslivets, Andrey N.
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Abstract
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.
Date
2019-11-27
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Beilstein-Institut
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Keywords
Diversity-oriented synthesis, Hydantoin, Nitrogen heterocycles, Rearrangement, Thiourea
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