Creation of 4-Quinolone Thioether and Selenoether Derivatives via Pd-NHC Catalysed Cross-Coupling Reaction

Prasanjit Ghosh; Sajal Das

doi:10.1055/s-0039-1690897

CC BY-NC-ND 4.0 · SynOpen 2020; 04(02): 33-37
DOI: 10.1055/s-0039-1690897

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Creation of 4-Quinolone Thioether and Selenoether Derivatives via Pd-NHC Catalysed Cross-Coupling Reaction

Prasanjit Ghosh

,

Sajal Das ∗

Abstract

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Abstract

Pd-NHC catalysed direct sulfenylation and selenylation of 3-iodo-4-quinolones has been developed. This protocol provides an alternative route for the construction of ipso-C–S and C–Se bond formation in 4-quinolones under aerobic conditions.

Key words

4-quinolone - Pd-NHC - sulfenylation - selenylation - cross-coupling

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References

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19 2-Phenyl-3-(phenylthio)quinolin-4(1H)-one (2a); Typical Procedure: 3-Iodo-2-phenyl-substituted 4-quinolone (0.25 mmol), thiophenol (0.375 mmol), DBU (0.5 mmol, 76 mg) and Pd-NHC (0.5 mol%, 1.2 mg) were dissolved in DMF (2 mL) in a 25 mL round-bottomed flask and the mixture was heated to 80 °C for 1–2 h. The mixture was then cooled, diluted with water, and the product was extracted with ethyl acetate (3 × 20 mL). The combined organic extracts were dried over anhydrous Na₂SO₄, filtered and concentrated under reduced pressure. The crude product was then purified by column chromatography, eluting with petroleum ether/ethyl acetate to give the product as a white solid (mp 191–193 °C). ¹H NMR (300 MHz, DMSO-d ₆): δ = 12.29 (s, 1 H), 8.11 (d, J = 7.8 Hz, 1 H), 7.71–7.73 (m, 2 H), 7.48–7.54 (m, 5 H), 7.41 (s, 1 H), 7.14–7.20 (m, 2 H), 6.97–7.05 (m, 3 H). ¹³C NMR (75 MHz, DMSO-d ₆): δ = 175.5, 139.9, 138.8, 135.5, 132.8, 130.2, 129.1, 129.0, 128.5, 125.9, 125.5, 124.8, 124.7, 124.5, 119.2, 108.5. HRMS (ESI+): m/z [M + H]⁺ calcd for C₂₁H₁₆NOS: 330.0952; found: 330.0972.

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