One-Pot Sequential Multistep Transformation of α,β-Unsaturated Trifluoromethyl Ketones: Facile Synthesis of Trifluoromethylated 2-Pyridones

Ning Lv; Yi-Qiang Tian; Fa-Guang Zhang; Jun-An Ma

doi:10.1055/s-0037-1612077

Synlett, Inhaltsverzeichnis

Synlett 2019; 30(05): 605-609
DOI: 10.1055/s-0037-1612077

letter

One-Pot Sequential Multistep Transformation of α,β-Unsaturated Trifluoromethyl Ketones: Facile Synthesis of Trifluoromethylated 2-Pyridones

Ning Lv

^aDepartment of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. of China

,

Yi-Qiang Tian

^aDepartment of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. of China

,

Fa-Guang Zhang *

^aDepartment of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. of China

,

Jun-An Ma*

^aDepartment of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin University, Tianjin 300072, P. R. of China

^bState Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China eMail: zhangfg1987@tju.edu.cn eMail: majun_an68@tju.edu.cn

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Abstract

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Abstract

A one-pot transformation of α,β-unsaturated trifluoromethyl ketones with 2-(phenylsulfinyl)acetamide to give trifluoromethylated 2-pyridones is realized. The reaction proceeds under mild conditions and involves multiple steps in an expeditious and controlled sequence to provide efficient access to a broad range of trifluoromethylated 2-pyridones in moderate to high yields. Moreover, further synthetic manipulations permit the routine synthesis of a diverse array of trifluoromethylated pyridines with good efficiency.

Key words

trifluoromethyl group - pyridones - trifluoromethylpyridines - one-pot synthesis - multistep reaction

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Referenzen

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14 6-(Trifluoromethyl)-2-pyridones 3a–r; General Procedure DBU (0.6 mmol, 89.7 μL) and the appropriate α,β-unsaturated trifluoromethyl ketone 2 (0.2 mmol, 1.0 equiv) were added to a mixture of 2-(phenylsulfinyl)acetamide (1; 0.4 mmol, 73.3 mg) and LiCl (0.6 mmol, 25.4 mg) in MeCN (4 mL) at r.t., and the mixture was stirred at r.t. for 4 h. When the trifluoromethyl ketone 2 was completely consumed (TLC), AcOH (1 mmol, 57.2 μL) was added, and the resulting mixture was refluxed for 10 h, then cooled to r.t. The reaction was then quenched with sat. aq NaHCO₃ and extracted with 10% MeOH–CHCl₃ (×3). The combined organic extracts were washed with brine, dried (Na₂SO₄), filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography [silica gel, CH₂Cl₂–MeOH (80:1)]. 4-Phenyl-6-(trifluoromethyl)pyridin-2(1H)-one (3a) White solid; yield: 77.5 mg (81.0%); mp 198.4–200.6 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 11.83 (s, 1 H), 7.86–7.81 (m, 2 H), 7.61 (s, 1 H), 7.51 (dd, J = 5.8, 4.6 Hz, 3 H), 7.21 (s, 1 H). ¹⁹F NMR (376 MHz, DMSO-d ₆): δ = –66.65 (s). ¹³C NMR (101 MHz, DMSO-d ₆): δ = 164.9, 152.2, 144.8 (q, J _C–F = 34.6 Hz), 136.2, 129.8, 129.2, 127.1, 121.5 (q, J _C–F = 272.4 Hz), 110.8, 110.3. 4-(2-Tolyl)-6-(trifluoromethyl)pyridin-2(1H)-one (3b) White solid; yield: 81.0 mg (80.0%); mp 98.7–99.9 °C. IR (neat): 1666, 1632, 1550, 1444, 1403, 1348, 1174, 1133, 965, 945, 840 cm^–1. ¹H NMR (400 MHz, DMSO-d ₆): δ = 11.85 (s, 1 H), 7.27 (d, J = 25.6 Hz, 5 H), 6.86 (s, 1 H), 2.23 (s, 3 H). ¹⁹F NMR (377 MHz, DMSO-d ₆): δ = –66.78 (s). ¹³C NMR (101 MHz, DMSO-d ₆): δ = 164.4 (s), 153.8 (s), 144.1 (q, J _C–F = 33.82 Hz), 137.8 (s), 134.7 (s), 130.7 (s), 129.0 (s), 128.8 (s), 126.2 (s), 121.5 (q, J _C–F = 272.33 Hz), 113.9 (s), 113.0 (s), 19.8 (s). HRMS (ESI): m/z [M + H]⁺ calcd for C₁₃H₁₁F₃NO: 254.0789; found: 254.0793.

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