Facile regiodivergent synthesis of spiro pyrrole-substituted pseudothiohydantoins and thiohydantoins via reaction of [e]-fused 1H-pyrrole-2,3-diones with thiourea

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 fou...

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Published inBeilstein journal of organic chemistry Vol. 15; no. 1; pp. 2864 - 2871
Main Authors Kobelev, Aleksandr I, Tretyakov, Nikita A, Stepanova, Ekaterina E, Dmitriev, Maksim V, Rubin, Michael, Maslivets, Andrey N
Format Journal Article
LanguageEnglish
Published Frankfurt am Main Beilstein-Institut zur Föerderung der Chemischen Wissenschaften 27.11.2019
Beilstein-Institut
Subjects
Catalysts
Chemistry
diversity-oriented synthesis
Full Research Paper
hydantoin
Investigations
nitrogen heterocycles
Pharmaceutical sciences
rearrangement
Temperature
Thiourea
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:2195-951X
1860-5397
1860-5397
DOI:10.3762/bjoc.15.280