Regioselective and Catalyst-Free Epoxidation of (E)-3-[3-(2-Hydroxyaryl)-3-oxoprop-1-en-1-yl]chromones

Rachid Ameraoui; Mohamed Hammadi; Oualid Talhi; Ridha Hassaine; Abdelghani Bouchama; Hasnia Abdeldjebar; Yamina Belmiloud; Meziane Brahimi; Filipe A. Almeida Paz; Khaldoun Bachari; Artur M. S. Silva

doi:10.1055/s-0037-1611082

Synlett, Table of Contents

Synlett 2018; 29(20): 2633-2637
DOI: 10.1055/s-0037-1611082

letter

Regioselective and Catalyst-Free Epoxidation of (E)-3-[3-(2-Hydroxyaryl)-3-oxoprop-1-en-1-yl]chromones

Authors

Rachid Ameraoui

^aLaboratoire de Synthèse Pétrochimique, Université M’Hamed Bougara, Boumerdès, Algeria Email: mohamedhammadi35@yahoo.fr

^bCentre de Recherche Scientifique et Technique en Analyses Physico-Chimiques CRAPC, BP 384, Bou-Ismail, 42004 Tipaza, Algeria
Mohamed Hammadi*

^aLaboratoire de Synthèse Pétrochimique, Université M’Hamed Bougara, Boumerdès, Algeria Email: mohamedhammadi35@yahoo.fr
Oualid Talhi*

^bCentre de Recherche Scientifique et Technique en Analyses Physico-Chimiques CRAPC, BP 384, Bou-Ismail, 42004 Tipaza, Algeria

^cQOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal Email: oualid.talhi@ua.pt Email: artur.silva@ua.pt
Ridha Hassaine

^bCentre de Recherche Scientifique et Technique en Analyses Physico-Chimiques CRAPC, BP 384, Bou-Ismail, 42004 Tipaza, Algeria

^dLaboratoire de Catalyse et Synthèse en Chimie Organique, Faculté des Sciences, Université de Tlemcen, Algeria
Abdelghani Bouchama

^bCentre de Recherche Scientifique et Technique en Analyses Physico-Chimiques CRAPC, BP 384, Bou-Ismail, 42004 Tipaza, Algeria

^eLaboratoire de Structure, Elaboration et Application des Matériaux Moléculaires (SEA2M), Faculté des Sciences et de la Technologie (FST), BP 188, Université Abdelhamid Benbadis, Mostaganem, Algeria
Hasnia Abdeldjebar

^fLaboratoire de Physico-Chimie Théorique et de Chimie Informatique, Faculté de Chimie, Université des Sciences et de la Technologie Houari Boumediene, 16000 Alger, Algeria
Yamina Belmiloud

^fLaboratoire de Physico-Chimie Théorique et de Chimie Informatique, Faculté de Chimie, Université des Sciences et de la Technologie Houari Boumediene, 16000 Alger, Algeria
Meziane Brahimi

^fLaboratoire de Physico-Chimie Théorique et de Chimie Informatique, Faculté de Chimie, Université des Sciences et de la Technologie Houari Boumediene, 16000 Alger, Algeria
Filipe A. Almeida Paz

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

^bCentre de Recherche Scientifique et Technique en Analyses Physico-Chimiques CRAPC, BP 384, Bou-Ismail, 42004 Tipaza, Algeria
Artur M. S. Silva *

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

Abstract

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Abstract

The uncatalyzed reaction of hydrogen peroxide with (E)-3-[3-(2-hydroxyaryl)-3-oxoprop-1-en-1-yl]chromones resulted in a regioselective epoxidation of the chromone intracyclic C(2)=C(3) double bond to afford unique isomeric (E)-7a-[3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]-1aH-oxireno[2,3-b]chromen-7(7aH)-ones in high yields. 2D NMR and single-crystal X-ray diffraction were used to elucidate the structures of the chromanone epoxides. Density functional theoretical studies demonstrated a high electrophilicity of the starting chromones.

Keywords

chromones - epoxidation - regioselectivity - NMR - X-ray diffraction - density functional theory

Full Text

References

References and Notes

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12 Regioselective Epoxidation of 3-[(2-Hydroxyaryl)-3-oxoprop-1-enyl]chromones 1a–b: General Procedure 30 vol% aq H₂O₂ (5 mL) was added to a solution of the appropriate chromenone 1a–e (1 mmol) in THF (20 mL), and the mixture was stirred for 30–60 min at r.t. while the reaction was monitored by TLC. Ice (50 g) was then added to the solution, and the product that precipitated was extracted with CH₂Cl₂ (2 × 50 mL). The solution was concentrated to 10 mL under vacuum, and hexane (10 mL) was added to crystallize the product.
13 7a-[(1E)-3-(2-Hydroxyphenyl)-3-oxoprop-1-en-1-yl]-1a,7a-dihydro-7H-oxireno[b]chromen-7-one (2a) Yellowish crystals; yield: 0.268 g (87%); mp 159–162 °C. ¹H NMR (300.13 MHz, CDCl₃): δ = 5.55 (s, 1 H, H-1a), 6.94 (ddd, J = 8.6, 7.5, 1.1 Hz, 1 H, H-5′′), 7.03 (dd, J = 8.5, 1.1 Hz, 1 H, H-3′′), 7.13 (dd, J = 8.4, 0.7 Hz, 1 H, H-3), 7.23 (dd, J = 8.4, 0.7 Hz, 1 H, H-5), 7.40 (d, J = 15.1 Hz, 1 H, H-2′), 7.48–7.56 (m, 1 H, H-4′′), 7.59 (d, J = 15.1 Hz, 1 H, H-1′), 7.59–7.67 (m, 1 H, H-4), 7.83 (dd, J = 8.6, 1.6 Hz, 1 H, H-6′′), 7.96–8.01 (m, 1 H, H-6), 12.82 (s, 1 H, 2′′-OH). ¹³C NMR (75.47 MHz, CDCl₃): δ = 33.4 (C-7a), 83.3 (C-1a), 118.0 (C-3), 118.6 (C-3′′), 119.1 (C-5′′), 119.3 (C-6a), 119.7 (C-1′′), 123.8 (C-5), 126.6 (C-2′), 127.6 (C-6), 130.1 (C-6′′), 136.37 and 136.52 (C-4 and C-1′), 137.1 (C-4′′), 154.9 (C-2a), 163.6 (C-2′′), 186.9 (C-7), 192.6 (C-3′). HRMS-ESI⁺: m/z [M + H]⁺ calcd for C₁₈H₁₃O₅: 309.0763; found: 309.0731.
14 Crystal data for compound 2a: C₁₈H₁₂O₅, M = 308.29, triclinic, space group P-1, Z = 2, a = 6.5204(5) Å, b = 9.4221(8) Å, c = 11.5726(9) Å, α = 84.252(6)°, β = 77.071(5)°, γ = 85.659(5)°, V = 688.42(10) Å³, μ(Mo-Kα) = 0.110 mm^–1, D _c = 1.487 g cm^–3, yellow block, crystal size 0.15 × 0.10 × 0.09 mm³. Of a total of 18928 reflections collected, 3676 were independent (R _int = 0.0431). Final R1 = 0.0470 [I > 2σ(I)] and wR2 = 0.1132 (all data). Data completeness to theta = 25.24°, 99.8%. Crystal data for compound 2e: C₁₉H₁₄O₅, M = 322.30, orthorhombic, space group P2₁2₁2₁, Z = 4, a = 4.8336(3) Å, b = 11.1047(7) Å, c = 27.0691(16) Å, V = 1452.95(15) Å³, μ(Mo-Kα) = 0.107 mm^–1, D _c = 1.473 g cm^–3, yellow plates, crystal size 0.13 × 0.09 × 0.04 mm³. Of a total of 32369 reflections collected, 3916 were independent (R _int = 0.0491). Final R1 = 0.0384 [I > 2σ(I)] and wR2 = 0.0896 (all data). Data completeness to theta = 25.24°, 99.7%.
15 CCDC 836401 and 836402 contain the supplementary crystallographic data for compounds 2a and 2e. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

Supplementary Material