We have synthesized and characterized a variety of fat-soluble, low-melting and medicinally useful 4-aryl-4H-chromenes from H-cardanol (side-chain perhydrogenated cardanol, 3-pentadecylphenol), a renewable and low-cost product from locally grown cashew nut trees (Anacardium occidentale L.). We incorporated H-cardanol into the aromatic rings of either 4H-chromene or phenol, or both. Substitution of C4SMe in N-methyl-4-(methylthio)-3-nitro-4H-chromene-2-amines with H-cardanol was regio-specific at the C6 position.
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KumarP.P., ParamashivappaR., VithayathilP.J., RaoP.V.S., RaoA.S. (2002) Process for isolation of cardanol from technical cashew (Anacardium occidentale L.) nut shell liquid. Journal of Agricultural and Food Chemistry, 50, 4705–4708.
4.
BalachandranV.S., JadhavS.R., VemulaP.K., JohnG. (2013) Recent advances in cardanol chemistry in a nutshell: from a nut to nanomaterials. Chemical Society Reviews, 42, 427–438.
5.
(a) VoirinC., CaillolS., SadavarteN.V., TawadeB.V., BoutevinabB., WadgaonkarP.P. (2014) Functionalization of cardanol: towards biobased polymers and additives, Polymer Chemistry, 5, 3142–3162; (b) Lubi MC, Thachil ET. (2000) Cashew nut shell liquid (CNSL) -a versatile monomer for polymer synthesis. Designed Monomers and Polymers, 3, 123–153.
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QuirinoR.L., GarrisonT.F., KesslerM.R. (2014) Matrices from vegetable oils, cashew nut shell liquid, and other relevant systems for biocomposite applications. Green Chemistry, 16, 1700–1715.
7.
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8.
MohapatraS., NandoG.B. (2014) Cardanol: A green substitute for aromatic oil as plasticizer in natural rubber. RSC Advances, 4, 15406–15418.
9.
KattimuttathuI.S., FoerstG., SchubertR., BartschE. (2012) Synthesis and micellization properties of new anionic reactive surfactants based on hydrogenated cardanol. Journal of Surfactants and Detergents, 15, 207–215.
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JunW., YuweiW., CuiqinL., XiaogangM., XiaofengZ. (2011) Synthesis of biomass cardanolsulfonate surfactant and its emulsification performance. Huaxue Yanjiu, 22, 47–51.
11.
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12.
RaoH.S.P., KamalrajM., SwainJ., MishraA.K. (2014) Characterization and phase transition study of a versatile molecular gel from a glucose-triazole hydrogenated cardanol conjugate. RSC Advances, 4, 12175–12181.
13.
MinigherA., BenedettiE., GiacomoO.D., CampanerP., AroulmojiV. (2009) Synthesis and characterization of novel cardanol based benzoxazines. Natural Product Communications, 4, 521–528.
14.
AttanasiO.A., Del SoleR., FilipponeaP., MazzettocS.E., MeleG., VasapolloG. (2004) Synthesis of novel lipophilic porphyrin-cardanol derivatives. Journal of Porphyrins and Phthalocyanines, 8, 1276–1284.
15.
(a) MeleG., Del SoleR., VasapolloG., Garcı'a-Lo'pezE., PalmisanoL., MazzettoS.E., AttanasidO.A., FilipponeP. (2004) Polycrystalline TiO2 impregnated with cardanol-based porphyrins for the photocatalytic degradation of 4-nitrophenol. Green Chemistry, 6, 604–608; (b) Attanasi OA, Ciccarella G, Filippone P, Mele G, Spadavecchia J, Vasapollo G. (2003) Novel phthalocyanines containing cardanol derivatives. Journal of Porphyrins and Phthalocyanines, 7, 52–57.
16.
AttanasiO.A., Del SoleR., FilipponeP., IanneR., MazzettoS.E., MeleG., VasapolloG. (2004) Synthesis of fullerene-cardanol derivatives. Synlett, 5, 799–802.
17.
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18.
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19.
KidwaiM., SaxenaS., KhanM.K.R., ThukralS.S. (2005) Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents. Bioorganic & Medicinal Chemistry Letters, 15, 4295–4298.
20.
(a) RaoH.S.P., GeethaK., KamalrajM. (2011) Synthesis of 4-(2-hydroxyaryl)–3-nitro-4H-chromenes. Tetrahedron, 67, 8146–8154; (b) Rao HSP, Geetha K, Kamalraj M. (2011) Synthesis of lactones of ortho-tyrosine, DOPA isomers and tryptophan-ortho-tyrosine hybrid amino acids. RSC Advances, 1, 1050–1059.
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23.
RekhaN., AshaS.K. (2009) Solvent-induced self-assembly in cardanol-based urethane methacrylate comb polymers. Journal of Polymer Science Part A: Polymer Chemistry, 47, 2996–3009.
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