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Research Article Open access CC BY 4.0

Parallel Synthesis of Aurones Using a Homogeneous Scavenger

Zachary E. Taylor, Scott T. Handy

Organics · pp. 51–58 · Published 28 Jan 2023

10.3390/org4010004

Abstract

The ability to synthesize arrays of related compounds quickly and with good purity has become critical for a rapid exploration of their properties for biological or material applications. While a number of methods have been developed to enable this combinatorial synthesis, the existing options were not readily appliable to the synthesis of aurones using the simple Knoevenagel condensation approach. In order to avoid the time, expense, and lowered yields associated with flash column chromatography, we developed a scavenging approach for their synthesis. This method uses an excess of aldehyde to ensure complete conversion to aurones, followed by selective removal of the remaining aldehyde using a simple, inexpensive scavenger – isoniazid – and subsequent extraction with dilute acid, to produce the desired compounds with good purity under operationally simple conditions. This approach is expected to be applicable to many other reactions involving aldehydes as one of the reactants.

Scavenger Aldehyde Knoevenagel condensation Chemistry Combinatorial chemistry Organic chemistry Computer science Radical

References (33)

  1. 1 Geissman, 1951, Benzalcoumaranones [DOI]
  2. 2 Mazziotti, I., Petrarolo, G., and La Motta, C. (2022). Aurones: A Golden Resource for Active Compounds. Molecules, 27. [DOI]
  3. 3 Sui, 2021, Recent advances on synthesis and biological qactivities of aurones [DOI]
  4. 4 Sutton, 2017, Antifungal activity of substituted aurones [DOI]
  5. 5 Park, 2017, Suppression of LPS-induced NF-κB activity in macrophages by the synthetic aurone, (Z)-2-((5-(hydroxymethyl) furan-2-yl) methylene) benzofuran-3(2H)-one [DOI]
  6. 6 Schmitt, 2019, A golden opportunity: Benzofuranone modifications of aurones and their influence on optical properties, toxicity, and potential as dyes [DOI]
  7. 7 Algahtani, F.M., Arivett, B.A., Taylor, Z.E., Handy, S.T., Farone, A.L., and Farone, M.B. (2019). Chemogenomic profiling to understand the antifungal action of a bioactive aurone compound. PLoS ONE, 14. [DOI]
  8. 8 Alqahtani, 2021, Combining Genome-Wide Gene Expression Analysis (RNA-seq) and a Gene Editing Platform (CRISPR-Cas9) to Uncover the Selectively Pro-oxidant Activity of Aurone Compounds Against Candida albicans [DOI]
  9. 9 Iwashina, 2000, The structure and distribution of the flavonoids in plants [DOI]
  10. 10 Agrawal, 2006, A New Process for the Synthesis of Aurones by Using Mercury (II) Acetate in Pyridine and Cupric Bromide in Dimethyl Sulfoxide
  11. 11 Thanigaimalai, 2010, Structural requirement of chalcones for the inhibitory activity of interleukin-5 [DOI]
  12. 12 Taylor, 2015, Metal-Free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts [DOI]
  13. 13 Harkat, 2008, Versatile and expeditious synthesis of aurones via Au I-catalyzed cyclization [DOI]
  14. 14 Liu, 2013, Construction of the flavones and aurones through regioselective carbonylative annulation of 2-bromophenols and terminal alkynes [DOI]
  15. 15 Qi, 2016, Selective Palladium-catalyzed carbonylative synthesis of aurones with formic acid as the CO source [DOI]
  16. 16 Kayal, 2016, Catalytic enantioselective cascade Michael/cyclization reaction of 3-isothiocyanato oxindoles with exocyclic α,β-unsaturated ketones en route to 3,2′-pyrrolidinyl bispirooxindoles [DOI]
  17. 17 Lee, 2015, Synthesis of aminoalkyl-substituted aurone derivatives as acetylcholinesterase inhibitors [DOI]
  18. 18 Varma, 1992, Alumina-mediated condensation. A simple synthesis of aurones [DOI]
  19. 19 Villemin, D., Martin, B., and Bar, N. (1998). Application of Microwave in Organic Synthesis. Dry Synthesis of 2-Arylmethylene-3(2)-naphthofuranones. Molecules, 3. [DOI]
  20. 20 Venkateswarlu, 2017, “On water” synthesis of aurones: First synthesis of 4,5,3′,4′,5′-pentamethoxy-6-hydroxyaurone from Smilax riparia [DOI]
  21. 21 Hawkins, 2013, Synthesis of aurones under neutral conditions using a deep eutectic solvent [DOI]
  22. 22 Zhang, W., and Cue, B.W. (2012). Green Techniques for Organic Synthesis and Medicinal Chemistry, John Wiley and Sons. [DOI]
  23. 23 Lu, 2009, Organic polymer supports for synthesis and for reagent and catalyst immobilization [DOI]
  24. 24 Moses, 2007, The growing applications of click chemistry [DOI]
  25. 25 Gouault, 2006, Method for the parallel synthesis of alpha-methylene-gamma-lactones from a fluorous acrylate [DOI]
  26. 26 Ley, 2000, Multi-step organic synthesis using solid-supported reagents and scavengers: A new paradigm in chemical library generation [DOI]
  27. 27 Boucher, 2017, Liquid–Liquid Extraction Protocol for the Removal of Aldehydes and Highly Reactive Ketones from Mixtures [DOI]
  28. 28 Kafle, A., Bhatarai, S., and Handy, S.T. (2020). An Unusual Triazole Synthesis from Aurones. Synthesis, 2337–2346. [DOI]
  29. 29 Taylor, 2017, Rapid synthesis of aurones under mild conditions using a combination of microwaves and deep eutectic solvents [DOI]
  30. 30 Xu, 2022, Synthesis of Fully Substituted 5-(o-Hydroxybenzoyl)imidazoles via Iodine-Promoted Domino Reactions of Aurones with Amidines [DOI]
  31. 31 Flynn, 1997, Chemical Library Purification Strategies Based on Principles of Complementary Molecular Reactivity and Molecular Recognition [DOI]
  32. 32 Kartnaller, 2015, Isoniazid as an Aldehdye Scavenger: Analysis of Its Kinetics, Selectivity, and Practicality in Purifying Organic Reactions
  33. 33 Kassehin, 2014, Solvent effect and catalysis in the synthesis of thiosemicarbazone derivatives from ketones and 4’-phenylthiosemicarbazide [DOI]

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