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

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

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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

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References

References and Notes

1a Sousa JL. C, Talhi O, Rocha DH. A, Pinto DC. G. A, Paz FA. A, Bachari K, Kirsch G, Silva AM. S. Synlett 2015; 26: 2724
1b Talhi O, Brodziak-Jaroz L, Panning J, Orlikova B, Zwergel C, Tzanova T, Philippot S, Pinto DC. G. A, Paz FA. A, Gerhäuser C, Dick TP, Jacob C, Diederich M, Bagrel D, Kirsch G, Silva AM. S. Eur. J. Org. Chem. 2016; 965
1c Sousa JL. C, Talhi O, Mendes RF, Paz FA. A, Bachari K, Silva AM. S. Eur. J. Org. Chem. 2016; 3949

2a Huang W, Liu M.-Z, Li Y, Tan Y, Yang G.-F. Bioorg. Med. Chem. 2007; 15: 5191
2b Wu C, Liu Y, Zeng H, Lui L, Wang D, Chen Y. Org. Biomol. Chem. 2011; 9: 253
2c Pintiala C, Lawson AM, Comesse S, Daïch A. Tetrahedron Lett. 2013; 54: 2853

3a Lévai A, Simon A, Jenei A, Kálmán G, Jekö J, Tóth G. ARKIVOK 2009; (xii): 161
3b Lechani N, Hamdi M, Kheddis-Boutemeur B, Talhi O, Laichi Y, Bachari K, Silva AM. S. Synlett 2018; 29: 1502
3c Lakhdari H, Talhi O, Hassaine R, Taibi N, Mendes RF, Paz FA. A, Bennamane N, Nedjar-Kolli B, Bachari K, Silva AM. S. Synlett 2018; 29: 1437

4 Ibrahim MA. ARKIVOK 2008; (xvii), 192

5a Abdel-Rahman AH, Hammouda MA. A, El-Desoky SI. Heteroat. Chem. 2005; 16: 20
5b Sosnovskikh VY, Moshkin VS, Irgashev RA. Tetrahedron Lett. 2006; 47: 8543
5c Sosnovskikh VY, Moshkin VS, Kodess MI. Tetrahedron Lett. 2008; 49: 6856
5d Hassaine R, Talhi O, Taibi N, Paz FA. A, Bensaid O, Bachari K, Silva AM. S. Synlett 2016; 27: 465

6a Weitz E, Scheffer A. Ber. Dtsch. Chem. Ges. 1921; 54: 2327
6b Donnelly JA, Keegan JR, Quigley K. Tetrahedron 1980; 36: 1671
6c Levai A, Patonay T, Székely A, Vass EB, Adam W, Jekö J. J. Heterocycl. Chem. 2000; 37: 1065

7 Bernini R, Mincione E, Coratti A, Fabrizib G, Battistuzzi G. Tetrahedron 2004; 60: 967

8a Santos CM. M, Silva AM. S, Cavaleiro JA. S, Patonay T, Lévai A. J. Heterocycl. Chem. 2006; 43: 1319
8b Patonay T, Kiss-Szikszai A, Silva VL. M, Silva AM. S, Pinto DC. G. A, Cavaleiro JA. S, Jekö J. Eur. J. Org. Chem. 2008; 1937

9a Hehre WJ, Radom L, Schleyer PV. R, Pople JA. Ab Initio Molecular Orbital Theory . Wiley-Interscience; New York: 1986
9b Lee C, Yang W, Parr RG. Phys. Rev. B 1988; 37: 785
9c Becke AD. J. Chem. Phys. 1993; 98: 5648

10 Frisch MJ, Trucks GW, Schlegel HB. et al. Gaussian 09 . Gaussian, Inc; Wallingford: 2016

11a Parr RG, Pearson RG. J. Am. Chem. Soc. 1983; 105: 7512
11b Schwenke DW, Truhlar DG. J. Chem. Phys. 1985; 82: 2418
11c Wolinski K, Hilton JF, Pulay P. J. Am. Chem. Soc. 1990; 112: 8251
11d Chattaraj PK, Lee H, Parr RG. J. Am. Chem. Soc. 1991; 113: 1855
11e Šponer JP, Hobza P. Int. J. Quantum Chem. 1996; 57: 959
11f Kohn W, Becke AD, Parr RG. J. Phys. Chem. 1996; 100: 12974
11g Chocholoušová J, Špirko V, Hobza P. Phys. Chem. Chem. Phys. 2004; 6: 37

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