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Synlett 2024; 35(07): 811-815
DOI: 10.1055/a-2179-6438
DOI: 10.1055/a-2179-6438
letter
Ruthenium(II)-Catalyzed Selective C–H Bond Activation of Biindoles and Coupling with Sulfoxonium: An Efficient Access to Pyrido[1,2-a:4,3-b′]diindole frameworks
K.S.K. thanks the University Grants Commission (UGC), New Delhi, for a faculty position under FRP. We also thank CSIR 02(0481)/23/EMR-II for funding this project.
Abstract
A ruthenium-catalyzed selective C–H functionalization/annulation cascade reaction of biindoles and sulfoxonium ylides has been developed. The reaction selectively provides pyrido[1,2-a:4,3-b′]diindole (5H-benzo[2,3]indolizino[7,8-b]indole) derivatives in good yields. A possible mechanism for the reaction pathway is proposed. More importantly, the present study provides a useful method for the construction of pyrido[1,2-a:4,3-b′]diindole frameworks.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2179-6438.
- Supporting Information
Publication History
Received: 25 May 2023
Accepted after revision: 21 September 2023
Accepted Manuscript online:
21 September 2023
Article published online:
30 October 2023
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- 15 Pyridodiindoles 3aa–ed; General Procedure An oven dried Schlenk tube equipped with a magnetic stirrer bar was charged with the appropriate diindole 1 (0.43 mmol), sulfoxonium ylide 2 (0.86 mmol) and DCE (2 mL). [RuCl2(p-cymene)]2 (10 mol%), AgSbF6 (20 mol%), and PivOH (1 equiv) were added, and Schlenk tube was closed with a N2-filled balloon. The resulting mixture was heated at 100 °C overnight. The mixture was then cooled to r.t., diluted with H2O (10 mL), and extracted with EtOAc (2 × 20 mL). The organic layers were collected, washed with brine, dried (Na2SO4), filtered, and concentrated under vacuum to give a crude product that was further purified by flash column chromatography [silica gel (100–200 mesh), hexane–EtOAc]. 7-Phenyl-5H-benzo[2,3]indolizino[7,8-b]indole (3aa) Brown solid; yield: 83%; mp = 175–177 °C; Rf = 0.6 (40% EtOAc–PE). 1H NMR (400 MHz, CDCl3): δ = 8.71 (s, 1 H), 8.27 (s, 1 H), 8.17 (d, J = 7.6 Hz, 1 H), 7.58–7.50 (m, 2 H), 7.68–7.66 (m, 4 H), 7.45 (t, J = 7.6 Hz, 1 H), 7.40–7.31 (m, 3 H), 7.16 (s, 1 H), 7.02 (t, J = 7.4 Hz, 1 H). 13C NMR (125 MHz, CDCl3): δ = 141.5, 139.0, 138.8, 138.7, 136.4, 134.3, 129.3 (2 C), 128.2 (3 C), 127.3, 124.5, 123.7, 121.8, 121.2, 120.3, 119.7, 119.4, 113.8, 110.7, 110.4, 106.0, 105.0. HRMS: (ESI+): m/z [M + H]+ calcd C24H17N2: 333.1386; found: 333.1384.
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