One-Pot Synthesis of Novel Highly Functionalized Furan-Based Polyphenolics

Joana L. C. Sousa; Oualid Talhi; Djenisa H. A. Rocha; Diana C. G. A. Pinto; Filipe A. Almeida Paz; Khaldoun Bachari; Gilbert Kirsch; Artur M. S. Silva

doi:10.1055/s-0035-1560580

Synlett, Inhaltsverzeichnis

Synlett 2015; 26(19): 2724-2729
DOI: 10.1055/s-0035-1560580

letter

One-Pot Synthesis of Novel Highly Functionalized Furan-Based Polyphenolics

Autor*innen

Joana L. C. Sousa

^aQOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal eMail: artur.silva@ua.pt eMail: oualid.talhi@ua.pt
Oualid Talhi*

^aQOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal eMail: artur.silva@ua.pt eMail: oualid.talhi@ua.pt

^cCentre de Recherche Scientifique et Technique en Analyses Physico-Chimiques CRAPC, BP384, Bou-Ismail, 42004, Tipaza, Algeria
Djenisa H. A. Rocha

^aQOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal eMail: artur.silva@ua.pt eMail: oualid.talhi@ua.pt
Diana C. G. A. Pinto

^aQOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal eMail: artur.silva@ua.pt eMail: oualid.talhi@ua.pt
Filipe A. Almeida Paz

^bCICECO – Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
Khaldoun Bachari

^cCentre de Recherche Scientifique et Technique en Analyses Physico-Chimiques CRAPC, BP384, Bou-Ismail, 42004, Tipaza, Algeria
Gilbert Kirsch

^dLaboratoire Structure et Réactivité des Systèmes Moléculaires Complexes, UMR 7565, Université de Lorraine, Avenue du Général Delestraint, 57070 Metz, France
Artur M. S. Silva*

^aQOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal eMail: artur.silva@ua.pt eMail: oualid.talhi@ua.pt

Abstract

Alle Artikel dieser Rubrik

Abstract

Novel, highly functionalized furan-based polyphenolics were prepared. The employed methodology involves a one-pot 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) catalyzed 1,4-conjugate addition of 1,3-dicarbonyl compounds on 3-bromochromones, furan heterocyclization, and chromanone ring opening.

Key words

furan - polyphenols - 1,3-dicarbonyl compounds - 1,4-conjugate addition - ring transformation

Volltext

Referenzen

References and Notes

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15 Synthesis of Furan-Based Polyphenolics 3a–i; General Procedure: 3-Bromo-4H-chromen-4-ones 1a,b and 1,3-dicarbonyl compounds 2b–h were prepared by following previously reported methods.^14,19 3-Bromochromone 1a,b (1.0 mmol) and 1,3-dicarbonyl compound 2a–h (1.1 mmol) were dissolved in THF (40 mL). DBU (1 drop per 50 mg of starting material) was then added and the resulting reaction mixture was stirred vigorously and heated to reflux. After 48 h, the solvent was evaporated under reduced pressure and the residue was purified by short plug silica gel column chromatography using dichloromethane as eluent. The purified products 3a–i were recrystallized from hexane/dichloromethane (1:1) by slow evaporation at 6 °C.
16 Typical Analytical Data: (4-Acetyl-5-methylfuran-2-yl)(2-hydroxyphenyl)methanone (3a): Yield: 171 mg (70%); yellow crystals; mp 99–100 °C (Lit.¹³ mp 98–100 °C). ¹H NMR (300.13 MHz, CDCl₃): δ = 11.94 (s, 1 H, 3′-OH), 8.19 (dd, J = 8.2, 1.6 Hz, 1 H, H-7′), 7.58 (s, 1 H, H-3), 7.54 (ddd, J = 8.5, 7.3, 1.6 Hz, 1 H, H-5′), 7.06 (dd, J = 8.5, 1.1 Hz, 1 H, H-4′), 6.99 (ddd, J = 8.2, 7.3, 1.1 Hz, 1 H, H-6′), 2.77 (s, 1 H, 5-CH₃), 2.50 (s, 1 H, 2′′-CH₃). ¹³C NMR (75.47 MHz, CDCl₃): δ = 193.2 (C-1′′), 184.4 (C-1′), 163.3 (C-3′), 163.2 (C-5), 149.2 (C-2), 136.4 (C-5′), 131.1 (C-7′), 123.4 (C-4), 121.1 (C-3), 119.2 (C-6′), 118.6 (C-4′), 118.5 (C-2′), 29.1 (2′′-CH₃), 15.1 (5-CH₃). HRMS (ESI⁺): m/z calcd for [C₁₄H₁₂O₄+H]⁺: 245.0808; found: 245.0821. (E)-[4-(2-Hydroxy-4-methoxybenzoyl)-5-(3,4-dimethoxystyryl)furan-2-yl](2-hydroxyphenyl)methanone (3b): Yield: 240 mg (48%); orange solid; mp 134–135 °C. ¹H NMR (500.13 MHz, CDCl₃): δ = 12.59 (s, 1 H, 3′′-OH), 11.95 (s, 1 H, 3′-OH), 8.22 (dd, J = 8.2, 1.6 Hz, 1 H, H-7′), 7.64 (d, J = 9.0 Hz, 1 H, H-7′′), 7.59 (s, 1 H, H-3), 7.57 (d, J = 16.5 Hz, 1 H, H-β), 7.56 (ddd, J = 8.4, 7.2, 1.6 Hz, 1 H, H-5′), 7.22 (d, J = 16.5 Hz, 1 H, H-α), 7.16 (dd, J = 8.4, 1.9 Hz, 1 H, H-6′′′), 7.10 (dd, J = 8.4, 1.0 Hz, 1 H, H-4′), 7.08 (d, J = 1.9 Hz, 1 H, H-2′′′), 7.02 (ddd, J = 8.2, 7.2, 1.0 Hz, 1 H, H-6′), 6.89 (d, J = 8.4 Hz, 1 H, H-5′′′), 6.54 (d, J = 2.5 Hz, 1 H, H-4′′), 6.49 (dd, J = 9.0, 2.5 Hz, 1 H, H-6′′), 3.95 (s, 3 H, 3′′′-OCH₃), 3.93 (s, 3 H, 4′′′-OCH₃), 3.89 (s, 3 H, 5′′-OCH₃). ¹³C NMR (125.77 MHz, CDCl₃): δ = 191.9 (C-1′′), 184.3 (C-1′), 166.6 (C-5′′), 166.2 (C-3′′), 163.3 (C-3′), 159.6 (C-5), 150.8 (C-4′′′), 149.3 (C-3′′′), 148.9 (C-2), 136.6 (C-β), 136.4 (C-5′), 133.7 (C-7′′), 131.0 (C-7′), 128.6 (C-1′′′), 123.0 (C-3), 122.0 (C-6′′′), 121.9 (C-4), 119.3 (C-6′), 118.8 (C-2′), 118.7 (C-4′), 114.0 (C-2′′), 112.1 (C-α), 111.2 (C-5′′′), 109.3 (C-2′′′), 108.0 (C-6′′), 101.3 (C-4′′), 56.02, 56.00 (3′′′, 4′′′-OCH₃), 55.77 (5′′-OCH₃). HRMS (ESI⁺): m/z calcd for [C₂₉H₂₄O₈+Na]⁺: 523.1363; found: 523.1344. (E)-[5-(4-Chlorostyryl)furan-2,4-diyl]bis[(2-hydroxyphenyl)-methanone] (3c): Yield: 249 mg (56%); yellow solid; mp 193–194 °C. ¹H NMR (300.13 MHz, CDCl₃): δ = 11.90 (s, 1 H, 3′-OH), 11.86 (s, 1 H, 3′′-OH), 8.21 (dd, J = 8.2, 1.5 Hz, 1 H, H-7′), 7.72 (dd, J = 8.1, 1.6 Hz, 1 H, H-7′′), 7.61 (s, 1 H, H-3), 7.60–7.49 (m, 4 H, H-5′,5′′, H-3′′′,5′′′), 7.53 (d, J = 16.3 Hz, 1 H, H-β), 7.38 (d, J = 8.6 Hz, 2 H, H-2′′′,6′′′), 7.37 (d, J = 16.3 Hz, 1 H, H-α), 7.12–7.09 (m, 2 H, H-4′,4′′), 7.03 (ddd, J = 8.1, 7.2, 1.2 Hz, 1 H, H-6′′), 6.96 (ddd, J = 8.2, 7.3, 1.1 Hz, 1 H, H-6′). ¹³C NMR (75.47 MHz, CDCl₃): δ = 193.5 (C-1′′), 184.4 (C-1′), 163.4 (C-3′), 163.0 (C-3′′), 159.2 (C-5), 149.3 (C-2), 137.0 (C-5′′), 136.6 (C-5′), 135.6 (C-1′′′), 135.5 (C-β), 133.9 (C-4′′′), 131.9 (C-7′′), 131.0 (C-7′), 129.3 (C-2′′′,6′′′), 128.8 (C-3′′′,5′′′), 122.7 (C-3), 122.5 (C-4), 119.9 (C-2′′), 119.4 (C-6′), 119.3 (C-6′′), 118.8 (C-4′,4′′), 118.7 (C-2′), 114.5 (C-α). HRMS (ESI⁺): m/z calcd for [C₂₆H₁₇O₅Cl+H]⁺: 445.0837; found: 445.0833.
17 Liu W, Jiang H, Zhang M, Qi C. J. Org. Chem. 2010; 75: 966
18 Crystal Data for 3a: C₁₄H₁₂O₄; M = 244.24; monoclinic; space group P2₁/n; Z = 4; a = 7.3330(9) Å, b = 10.5928(14) Å, c = 15.0866(19) Å, β = 90.962(4)°; V = 1171.7(3) Å³; μ(Mo-K_α) = 0.102 mm^–1; D _c = 1.385 g cm^–3; colorless needle; crystal size 0.28 × 0.10 × 0.08 mm³. Of a total of 8785 reflections collected, 2126 were independent (R _int = 0.0685). Final R1 = 0.0494 [I > 2σ(I)] and wR2 = 0.1286 (all data). Data completeness to θ = 25.24°, 99.2%. Crystallographic data for 3a has been deposited into the Cambridge Crystallographic Data Centre with the deposition number CCDC 1409624.

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