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
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 pyrr...
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| Format: | Article |
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MDPI AG
2023-02-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/24/4/3404 |
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| author | Ludmila A. Oparina Nikita A. Kolyvanov Igor A. Ushakov Lina P. Nikitina Olga V. Petrova Lyubov N. Sobenina Konstantin B. Petrushenko Boris A. Trofimov |
| author_facet | Ludmila A. Oparina Nikita A. Kolyvanov Igor A. Ushakov Lina P. Nikitina Olga V. Petrova Lyubov N. Sobenina Konstantin B. Petrushenko Boris A. Trofimov |
| author_sort | Ludmila A. Oparina |
| collection | DOAJ |
| description | 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 arsenal of chemical methods promoting drug discovery. Photophysical studies show that some of the synthesized compounds, e.g., benzo[<i>g</i>]pyrroloimidazoindoles, are prospective candidates for TADF emitters of OLED. |
| first_indexed | 2024-03-11T08:42:55Z |
| format | Article |
| id | doaj.art-610eb6aa5df0421ab62e14a150990920 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-11T08:42:55Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-610eb6aa5df0421ab62e14a1509909202023-11-16T20:59:29ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672023-02-01244340410.3390/ijms24043404Contributing 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>-PyrrolinesLudmila A. Oparina0Nikita A. Kolyvanov1Igor A. Ushakov2Lina P. Nikitina3Olga V. Petrova4Lyubov N. Sobenina5Konstantin B. Petrushenko6Boris A. Trofimov7A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, RussiaAvailable 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 arsenal of chemical methods promoting drug discovery. Photophysical studies show that some of the synthesized compounds, e.g., benzo[<i>g</i>]pyrroloimidazoindoles, are prospective candidates for TADF emitters of OLED.https://www.mdpi.com/1422-0067/24/4/3404acylethynylcycloalka[<i>b</i>]pyrrolesΔ<sup>1</sup>-pyrrolines[3+2] annulationpyrrolo[1′,2′:2,3]imidazo[1,5-<i>a</i>]indolescyclohepta[4,5]pyrrolo[1,2-<i>c</i>]pyrrolo[1,2-<i>a</i>]imidazoles |
| spellingShingle | Ludmila A. Oparina Nikita A. Kolyvanov Igor A. Ushakov Lina P. Nikitina Olga V. Petrova Lyubov N. Sobenina Konstantin B. Petrushenko Boris A. Trofimov 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 International Journal of Molecular Sciences acylethynylcycloalka[<i>b</i>]pyrroles Δ<sup>1</sup>-pyrrolines [3+2] annulation pyrrolo[1′,2′:2,3]imidazo[1,5-<i>a</i>]indoles cyclohepta[4,5]pyrrolo[1,2-<i>c</i>]pyrrolo[1,2-<i>a</i>]imidazoles |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | acylethynylcycloalka[<i>b</i>]pyrroles Δ<sup>1</sup>-pyrrolines [3+2] annulation pyrrolo[1′,2′:2,3]imidazo[1,5-<i>a</i>]indoles cyclohepta[4,5]pyrrolo[1,2-<i>c</i>]pyrrolo[1,2-<i>a</i>]imidazoles |
| url | https://www.mdpi.com/1422-0067/24/4/3404 |
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