Contributing to Biochemistry and Optoelectronics: Pyrrolo[1′,2′:2,3]imidazo[1,5-Ia/I]indoles and Cyclohepta[4,5]pyrrolo[1,2-Ic/I]pyrrolo[1,2-Ia/I]imidazoles via [3+2] Annulation of Acylethynylcycloalka[Ib/I]pyrroles with Δ[sup.1]-Pyrrolines

Available pyrrolylalkynones with tetrahydroindolyl, cycloalkanopyrrolyl, and dihydrobenzo[g]indolyl moieties, acylethynylcycloalka[b]pyrroles, are readily annulated with Δ[sup.1]-pyrrolines (MeCN/THF, 70 °C, 8 h) to afford a series of novel pyrrolo[1′,2′:2,3]imidazo[1,5-a]indoles and cyclohepta[4,5]...

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Published inInternational journal of molecular sciences Vol. 24; no. 4
Main Authors Oparina, Ludmila A, Kolyvanov, Nikita A, Ushakov, Igor A, Nikitina, Lina P, Petrova, Olga V, Sobenina, Lyubov N, Petrushenko, Konstantin B, Trofimov, Boris A
Format Journal Article
LanguageEnglish
Published MDPI AG 01.02.2023
Subjects
Biochemistry
Drug discovery
Light-emitting diodes
Optoelectronics industry
Massachusetts
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Summary:Available pyrrolylalkynones with tetrahydroindolyl, cycloalkanopyrrolyl, and dihydrobenzo[g]indolyl moieties, acylethynylcycloalka[b]pyrroles, are readily annulated with Δ[sup.1]-pyrrolines (MeCN/THF, 70 °C, 8 h) to afford a series of novel pyrrolo[1′,2′:2,3]imidazo[1,5-a]indoles and cyclohepta[4,5]pyrrolo[1,2-c]pyrrolo[1,2-a]imidazoles functionalized with an acylethenyl group in up to an 81% yield. This original synthetic approach contributes to the arsenal of chemical methods promoting drug discovery. Photophysical studies show that some of the synthesized compounds, e.g., benzo[g]pyrroloimidazoindoles, are prospective candidates for TADF emitters of OLED.
ISSN:1422-0067
1422-0067
DOI:10.3390/ijms24043404