Hydrogen-Bonded Xanthones as Potential UV Absorbers: The Synthesis of Xanthones from Bio-Renewable Cardanol Utilizing a Ceric Ammonium Sulfate (CAS)-Mediated Oxidation Reaction

Abstract

The synthesis of hydrogen-bonded xanthones by using biorenewable hydrogenated cardanol (3-pentadecylphenol) is described. Hydrogenated cardanol was initially converted into various hydroxybenzophenones. These benzophenones were converted into xanthones by utilizing an oxidative ceric ammonium sulfate-mediated reaction. A subsequent ruthenium-mediated late-stage oxidation of the xanthones provided hydrogen-bonded xanthones, which displayed good UVA and UVB absorbing properties.

Key words

cardanols - benzophenones - ceric ammonium sulfate - oxidative addition - xanthones - UV absorbers

• References

• 1 New address: Aliyaah Rahman, Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin, Germany.
• 2 Le Pogam P, Boustie J. Molecules 2016; 21: 294
• 3 Masters K.-S, Bräse S. Chem. Rev. 2012; 112: 3717
• 4 Roberts JC. Chem. Rev. 1961; 61: 591
• 5a de Koning CB, Giles RG. F, Engelhardt LM, White AH. J. Chem. Soc., Perkin Trans. 1 1988; 3209
• 5b Kupchan SM, Streelman DR, Sneden AT. J. Nat. Prod. 1980; 43: 296
• 6 Ke H, Morrisey JM, Qu S, Chantarasriwong O, Mather MW, Theodorakis EA, Vaidya AB. Antimicrob. Agents Chemother. 2017; 61: e01220-16
• 7 Feng Z, Lu X, Gan L, Zhang Q, Lin L. Molecules 2020; 25: 598
• 8 Pailee P, Kuhakarn C, Sangsuwan C, Hongthong S, Piyachaturawat P, Suksen K, Jariyawat S, Akkarawongsapat R, Limthongkul J, Napaswad C, Kongsaeree P, Prabpai S, Jaietch T, Pohmakotr M, Tuchinda P, Reutrakul V. Phytochemistry 2018; 147: 68
• 9a Sousa ME, Pinto MM. M. Curr. Med. Chem. 2005; 12: 2447
• 9b Winter DK, Sloman DL, Porco JA. Jr. Nat. Prod. Rep. 2013; 30: 382
• 10 Johnson MM, Naidoo JM, Fernandes MA, Mmutlane EM, van Otterlo WA. L, de Koning CB. J. Org. Chem. 2010; 75: 8701 ; corrigendum: J. Org. Chem. 2019, 84, 472
• 11 Dam J, Bode ML, de Koning CB. J. Org. Chem. 2019; 84: 150
• 12 Ngwira KJ, Kühlborn J, Mgani QA, de Koning CB, Opatz T. Eur. J. Org. Chem. 2019; 4778

Other related oxidative cyclization reactions have been reported; for an example of a phenol-mediated oxidative cyclization with Ag₂CO₃, see:
• 13a Fuse S, Matsumura K, Johmoto K, Uekusa H, Tanaka H, Hirose T, Sunazuka T, Õmura S, Takahashi T. Chem. Eur. J. 2016; 22: 18450

For a DDQ oxidation of 1,4-hydroquinones to afford spiro-type compounds, see ref. 5a and:
• 13b Lewis JR, Paul JG. J. Chem. Soc., Perkin Trans. 1 1981; 770
• 14 Eaton PE, Carlson GR, Lee JT. J. Org. Chem. 1973; 38: 4071
• 15a Shan G, Han X, Lin Y, Yu S, Rao Y. Org. Biomol. Chem. 2013; 11: 2318
• 15b Thirunavukkarasu VS, Ackermann L. Org. Lett. 2012; 14: 6206
• 15c Dias GG, Rogge T, Kuniyil R, Jacob C, Menna-Barreto RF. S, da Silva EN. Jr, Ackermann L. Chem. Commun. 2018; 54: 12840
• 16 For a discussion on triazine UV absorbers that require hydrogen-bonding to efficiently transform UV radiation into thermal energy by a process called phototautomerism, see: Hüglin D. Chimia 2016; 70: 496
• 17 Chawla HM, Pant N, Kumar S, Mrig S, Srivastava B, Kumar N, Black DStC. J. Photochem. Photobiol., B 2011; 105: 25
• 18 Mulay SV, Amit Bhowmik V, Fernandes R. Eur. J. Org. Chem. 2019; 4931