Phosphine-Mediated [3+2] Cyclization for the Synthesis of Coumarin-Based CF₃-Containing Furanones

Abstract

A tertiary phosphine-mediated [3+2] cyclization reaction of ynones with fluorinated coumarin derivatives has been developed to give a series of coumarin-based CF₃-containing furanones in moderate to good yields under mild reaction conditions. Preliminary investigation into their antitumor activities is also presented.

Key words

phosphine - cyclization - coumarin - furanone

Publikationsverlauf

Eingereicht: 28. Dezember 2022

Angenommen nach Revision: 06. März 2023

Artikel online veröffentlicht:
05. April 2023

• References and Notes

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• 14 General Synthetic Method for Compound 3a–p To a solution of 2,2,2-trifluoroacetaldehyde coumarin 1 (0.2 mmol, 1.0 equiv) and ynone 2 (0.30 mmol, 1.5 equiv) in TFE (2 mL) was added PPh₂Et (0.2 mmol, 1.0 equiv), followed by the addition of PhCOOH (0.06 mmol, 0.3 equiv). The resulting mixture was stirred under nitrogen atmosphere at 60 °C for 2–4 h. Upon completion of the reaction, the solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (hexane/EtOAc = 20:1 to 3:1) to afford cyclization adduct 3. (Z)-3-[5-Benzylidene-4-oxo-2-(trifluoromethyl)tetrahydrofuran-2-yl]-2H-chromen-2-one (3a) 67.9 mg, 88% yield; a yellow solid; mp 166.5–166.8 °C. ¹H NMR (500 MHz, CDCl₃): δ = 8.27 (s, 1 H), 7.88–7.77 (m, 2 H), 7.69–7.58 (m, 2 H), 7.54–7.46 (m, 2 H), 7.43–7.33 (m, 3 H), 6.50 (s, 1 H), 3.43 (dd, J = 51.6, 19.5 Hz, 2 H). ¹⁹F NMR (471 MHz, CDCl₃): δ = –79.53. ¹³C NMR (126 MHz, CDCl₃): δ = 194.3, 158.2, 154.0, 144.7, 143.7, 133.4, 132.6, 130.5, 129.3, 129.2, 129.0, 125.0, 123.9 (q, J = 284.8 Hz), 121.6, 117.9, 116.7, 108.0, 82.1 (q, J = 31.5 Hz), 40.1. HRMS: m/z calcd for C₂₁H₁₄F₃O₄ [M + H]⁺ = 387.0843; found: 387.0839. Crystal Data for C₂₁H₁₃F₃O₄ (3a) M = 386.31 g/mol; monoclinic, space group P2₁/n (no. 14), a = 9.6912(10) Å, b = 16.2258(16) Å, c = 11.1571(11) Å, β = 105.913(3) , V = 1687.2(3) ų, Z = 4, T = 170.00 K, μ(Ga Kα) = 0.695 mm^–1, D_calc = 1.521 g/cm³, 31154 reflections measured (8.596° ≤ 2Θ ≤ 121.276°), 3813 unique (R _int = 0.0553, R _σ = 0.0458) which were used in all calculations. The final R ₁ was 0.0425 (I > 2σ(I)) and wR ₂ was 0.1163 (all data).
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