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Contributing to Biochemistry and Optoelectronics: Pyrrolo[1',2':2,3]imidazo[1,5-a]indoles and Cyclohepta[4,5]pyrrolo[1,2-c]pyrrolo[1,2-a]imidazoles via [3+2] Annulation of Acylethynylcycloalka[b]pyrroles with Δ1-Pyrrolines.

ABSTRACT: Available pyrrolylalkynones with tetrahydroindolyl, cycloalkanopyrrolyl, and dihydrobenzo[g]indolyl moieties, acylethynylcycloalka[b]pyrroles, are readily annulated with Δ1-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.

SUBMITTER: Oparina LA 

PROVIDER: S-EPMC9959468 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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Contributing to Biochemistry and Optoelectronics: Pyrrolo[1',2':2,3]imidazo[1,5-<i>a</i>]indoles and Cyclohepta[4,5]pyrrolo[1,2-<i>c</i>]pyrrolo[1,2-<i>a</i>]imidazoles via [3+2] Annulation of Acylethynylcycloalka[<i>b</i>]pyrroles with Δ<sup>1</sup>-Pyrrolines.

Oparina Ludmila A LA   Kolyvanov Nikita A NA   Ushakov Igor A IA   Nikitina Lina P LP   Petrova Olga V OV   Sobenina Lyubov N LN   Petrushenko Konstantin B KB   Trofimov Boris A BA  

International journal of molecular sciences 20230208 4

Available pyrrolylalkynones with tetrahydroindolyl, cycloalkanopyrrolyl, and dihydrobenzo[<i>g</i>]indolyl moieties, acylethynylcycloalka[<i>b</i>]pyrroles, are readily annulated with Δ<sup>1</sup>-pyrrolines (MeCN/THF, 70 °C, 8 h) to afford a series of novel pyrrolo[1',2':2,3]imidazo[1,5-<i>a</i>]indoles and cyclohepta[4,5]pyrrolo[1,2-<i>c</i>]pyrrolo[1,2-<i>a</i>]imidazoles functionalized with an acylethenyl group in up to an 81% yield. This original synthetic approach contributes to the arsen  ...[more]

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