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

Wenhao Gan; Junfeng Fu; Zhixiang Zhou; Sheng Cao; Zhipeng Zhang; Yongjiang Wang; Xiaoyu Han

doi:10.1055/s-0042-1751434

Synlett, Table of Contents

Synlett 2023; 34(13): 1587-1592
DOI: 10.1055/s-0042-1751434

letter

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

Wenhao Gan‡

,

Junfeng Fu‡

,

Zhixiang Zhou

,

Sheng Cao

,

Zhipeng Zhang

,

Yongjiang Wang∗

,

Xiaoyu Han ∗

Abstract

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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

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References

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) Å³, 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).
15 CCDC 2243264 contains the supplementary crystallographic data for compound 3a. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures

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