Synthesis of imidazole-fused pentacyclic pyrrolo[3,4-c]coumarins via base-promoted rearrangement of coumarin-substituted N-heterocyclic carbene precursors

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dc.contributor.authorKaratas, Mert Olgun
dc.contributor.authorOzdemir, Namik
dc.contributor.authorKucukbay, Hasan
dc.date.accessioned2026-04-04T13:34:40Z
dc.date.available2026-04-04T13:34:40Z
dc.date.issued2024
dc.departmentİnönü Üniversitesi
dc.description.abstractPentacyclic pyrrolocoumarin scaffolds are unique structural motifs that form the backbone of many bioactive compounds. Herein, we report the first-time synthesis of imidazole-fused pentacyclic pyrrolo[3,4-c]coumarin derivatives (2) through the stoichiometric reaction between coumarin-substituted N-heterocyclic carbene (NHC) precursors (1) and Pd(OAc)(2), in the presence of an external base. Control experiments revealed that the base-promoted rearrangement of the NHC precursors yields N-(alkyl)aniline-substituted pyrrolo[3,4-c]coumarin derivatives (3), wherein the imidazole ring is opened. Additionally, the formation of 2via the reaction of 3 and Pd(OAc)(2 )indicated that the formation of pentacyclic pyrrolo[3,4-c]coumarin occurs via the base-promoted rearrangement product of NHC precursors.
dc.description.sponsorshipScientific Research Projects Unit of Idot;noenue University [FLO-2022-3052]
dc.description.sponsorshipThis was supported by the Scientific Research Projects Unit of & Idot;noenue University (project no. FLO-2022-3052). M. O. K. thanks Assoc. Prof. Dr Serkan Dayan for the laboratory facilities for part of the experiments conducted in this study after the devastating earthquake on February 6, 2023.
dc.identifier.doi10.1039/d4nj03146f
dc.identifier.endpage16682
dc.identifier.issn1144-0546
dc.identifier.issn1369-9261
dc.identifier.issue38
dc.identifier.orcid0000-0001-8500-2088
dc.identifier.orcid0000-0002-7180-9486
dc.identifier.orcid0000-0003-3371-9874
dc.identifier.scopus2-s2.0-85203787765
dc.identifier.scopusqualityQ2
dc.identifier.startpage16676
dc.identifier.urihttps://doi.org/10.1039/d4nj03146f
dc.identifier.urihttps://hdl.handle.net/11616/109313
dc.identifier.volume48
dc.identifier.wosWOS:001311226200001
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherRoyal Soc Chemistry
dc.relation.ispartofNew Journal of Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250329
dc.subjectComplexes
dc.subjectLamellarins
dc.subjectInhibitors
dc.subjectSilver(I)
dc.subjectMoisture
dc.subjectNhc
dc.titleSynthesis of imidazole-fused pentacyclic pyrrolo[3,4-c]coumarins via base-promoted rearrangement of coumarin-substituted N-heterocyclic carbene precursors
dc.typeArticle

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