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

Aleksandr I Kobelev; Nikita A Tretyakov; Ekaterina E Stepanova; Maksim V Dmitriev; Michael Rubin; Andrey N Maslivets

doi:10.3762/bjoc.15.280

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

Beilstein J Org Chem. 2019 Nov 27:15:2864-2871. doi: 10.3762/bjoc.15.280. eCollection 2019.

Authors

Aleksandr I Kobelev¹, Nikita A Tretyakov¹, Ekaterina E Stepanova¹, Maksim V Dmitriev¹, Michael Rubin^{2

3}, Andrey N Maslivets¹

Affiliations

¹ Department of Chemistry, Perm State University, ul. Bukireva 15, Perm 614990, Russian Federation.
² Department of Chemistry, University of Kansas, 1567 Irving Hill Road, Lawrence, Kansas 66045, United States.
³ Department of Chemistry, North Caucasus Federal University, ul. Pushkina 1a, Stavropol 355009, Russian Federation.

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.

Keywords: diversity-oriented synthesis; hydantoin; nitrogen heterocycles; rearrangement; thiourea.