Ultrasound-enhanced one-pot synthesis of 3-(Het)arylmethyl-4-hydroxycoumarins in water

Ultrasonics Sonochemistry - Tập 18 - Trang 652-660 - 2011
Giovanni Palmisano1, Francesco Tibiletti1, Andrea Penoni1, Francesca Colombo1, Stefano Tollari1, Davide Garella2, Silvia Tagliapietra2, Giancarlo Cravotto2
1Dipartimento di Scienze Chimiche e Ambientali, Università dell’Insubria, via Valleggio 11, 22100 Como, Italy
2Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Via P. Giuria 9, 10235 Torino, Italy

Tài liệu tham khảo

Salinas-Jazmín, 2010, Antimetastatic, antineoplastic, and toxic effects of 4-hydroxycoumarin in a preclinical mouse melanoma model, Cancer Chem. Pharm., 65, 931, 10.1007/s00280-009-1100-z Farag, 2010, Design, synthesis and docking studies of new furobenzopyranones and pyranobenzopyranones as photoreagent towards DNA and as antimicrobial agents, Eur. J. Med. Chem., 45, 317, 10.1016/j.ejmech.2009.10.016 Petersen, 2009, Anticoagulation therapy for prevention and treatment of venous thromboembolic events in cancer patients: a review of current guidelines, Cancer Treat. Rev., 35, 754, 10.1016/j.ctrv.2009.08.009 Cullen, 2003, Dicumarol inhibition of NADPH: quinone oxidoreductase induces growth inhibition of pancreatic cancer via a superoxide-mediated mechanism, Cancer Res., 63, 5513 Mironov, 2004, Dicumarol, an inhibitor of ADP-ribosylation of CtBP3/BARS, fragments Golgi non-compact tubular zones and inhibits intra-Golgi transport, Eur. J. Cell. Biol., 83, 263, 10.1078/0171-9335-00377 Prajapati, 2009, The search for potent small molecule NNRTIs: a review, Bio. Med. Chem., 17, 5744, 10.1016/j.bmc.2009.06.060 Mahajan, 2009, Synthesis studies of new 2-(coumarin-4-yloxy)-4,6(substituted)-s-triazine derivatives as potential anti-HIV agents, Archiv. Pharm., 342, 281, 10.1002/ardp.200800149 Liu, 2009, Study on the inhibitory mechanism and bonding mode of the hydroxycoumarin compound NSC 158393 to HIV-1 integrase by molecular modelling, Biopolymers, 91, 700, 10.1002/bip.21211 Dubey, 2007, Development of integrase inhibitors for treatment of AIDS: an overview, Eur. J. Med. Chem., 42, 1159, 10.1016/j.ejmech.2007.01.024 Kirkiacharian, 2002, Structure-activity relationship of some 3-substituted-4-hydroxycoumatins as HIV-1 protease inhibitors, Farmaco, 57, 703, 10.1016/S0014-827X(02)01264-8 Athanasellis, 2004, Novel short-step synthesis of functionalized γ-phenyl-β-hydroxybutenoates and their cyclization to 4-hydroxycoumarins via the N-hydroxybenzotriazole methodology, Synthesis, 11, 1775 Appendino, 1992, A regioselective synthesis of 3-isoprenyl-4-hydroxycoumarins, Synth. Commun., 22, 2205, 10.1080/00397919208019073 Stahmann, 1943, Studies on 4-hydroxycoumarins. I. The synthesis of 4-hydroxycoumarins, J. Am. Chem. Soc., 65, 2285, 10.1021/ja01252a007 Silverman, 1980, A model for a molecular mechanism of anticoagulant activity of 3-substituted 4-hydroxycoumarins, J. Am. Chem. Soc., 102, 5421, 10.1021/ja00536a064 Trivedi, 2001, Chemistry of 4-hydroxycoumarins, J. Indian Chem. Soc., 78, 579 Babin, 1981, Nouveau mode de cyclization de céto-ylures. Application à une synthèse originale d’acyl-3-hydroxy-4-coumarines et de l’hydroxy-11-benzo[b]12[h] xanthone-12, Tetrahedron, 37, 1131, 10.1016/S0040-4020(01)92042-3 Eiden, 1983, Synthese und Reaktionen von 3-Acyl-2-methylthiochromonen, Arch. Pharm., 316, 34, 10.1002/ardp.19833160109 Thaisrivongs, 1995, Structure-based design of novel HIV protease inhibitors: carboxamide-containing 4-hydroxycoumarins and 4-hydroxy-2-pyrones as potent nonpeptidic inhibitors, J. Med. Chem., 38, 3624, 10.1021/jm00018a023 Silverman, 1981, Model studies for a molecular mechanism of action of oral anticoagulants, J. Am. Chem. Soc., 103, 3910, 10.1021/ja00403a050 Appendino, 1991, Synthesis of 3-alkyl-4-hydroxycoumarins by reductive fragmentation of 3,3′-alkylidene-4,4′-dihydroxybis(coumarins), Helv. Chim. Acta, 74, 1451, 10.1002/hlca.19910740708 Kalinin, 1998, Directed ortho metalation–cross coupling links. Carbamoyl rendition of the Baker–Venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins, Tetrahedron Lett., 39, 4995, 10.1016/S0040-4039(98)00977-0 Ikawa, 1944, Studies on 4-hydroxycoumarins. V. The condensation of α,β-unsaturated ketones with 4-hydroxycoumarin, J. Am. Chem. Soc., 66, 902, 10.1021/ja01234a019 Ziegler, 1957, Zur Chemie des 4-Hydroxy-cumarins, Monatsh. Chem., 88, 25, 10.1007/BF01075426 Appendino, 1990, The chemistry of coumarin derivatives. Reaction of 4-hydroxycoumarin with α,β-unsaturated aldehydes, Helv. Chim. Acta, 73, 1865, 10.1002/hlca.19900730709 Nutaitis, 1980, Reduction of isopropylidene acylmalonates, 5-acylbarbituric acids, and 3-acyl-4-hydroxycoumarins to the corresponding alkyl derivatives by sodium cyanoborohydride-acetic acid, J. Org. Chem., 45, 4606, 10.1021/jo01311a011 Zhao, 1997, Coumarin-based inhibitors of HIV integrase, J. Med. Chem., 40, 242, 10.1021/jm960450v Tóth, 1999, A simple procedure for the alkylation of 4-hydroxycoumarins at C-3 position, Org. Prep. Proced. Int., 31, 222, 10.1080/00304949909355718 Zhu, 2002, Phenyliodonium zwitterion as an efficient electrophile in the palladium-catalyzed Suzuki-type reaction: a novel method for the synthesis of 3-aryl-4-hydroxycoumarins, Org. Lett., 4, 3333, 10.1021/ol020159b Goldoni, 2005, The rhodium carbenoid rout to 3-aryl-4-hydroxycoumarins: synthesis of derrusnin, Synlett, 6, 927 Cenini, 2002, Diruthenium(II,II) tetrakis(acetate)as a catalyst of choice for intermolecular inserion of stabilized diazocompound into O–H bonds, Tetrahedron Lett., 43, 3637, 10.1016/S0040-4039(02)00618-4 Cenini, 1999, Polyoxygenated coumarins. Oxonium ylides en route to polyoxa-macrocyclic coumarins, Tetrahedron, 55, 6577, 10.1016/S0040-4020(99)00291-4 Tietze, 2005, 121 Shen, 2008, Reduction of N-/alkoxy(aryl)methyl)benzamide compounds by a Hantzsch ester 1,4-dihydropyridine using Pd/C as a catalyst, Catal. Lett., 126, 361, 10.1007/s10562-008-9631-1 Ramachary, 2008, Direct amino acid-catalyzed cascade biomimetic reductive alkylations: application to the asymmetric synthesis of Hajos–Parrish ketone analogues, Org. Biomol. Chem., 6, 4176, 10.1039/b807999d Hirota, 1985, Ring transformation of 5-(2-carbamoylvinyl)uracil derivatives to 5-carbamoylpyridin-2-ones, J. Org. Chem., 50, 1512, 10.1021/jo00209a030 Costero, 2005, Cation and anion fluorescent electrochemical sensors derived from 4,4′-substituted biphenyl, Tetrahedron, 61, 10309, 10.1016/j.tet.2005.08.010 Zolfigol, 2004, Synthesis of 1,4-dihydropyridines under solvent-free conditions, Synlett, 5, 827, 10.1055/s-2004-820010 Knierzinger, 1980, Syntheses of fluorescent dyes IX New 4-hydroxycoumarins, 4-hydroxy-2-quinolones, 2H 5H-pyrano[3,2-c]benzopyran-2,5-diones and 2H 5H-pyrano[3,2-c]quinoline-2,5-diones, J. Het. Chem., 17, 225, 10.1002/jhet.5570170204 Cravotto, 2008, Improved extraction of natural matrices under high-intensity ultrasound and microwave, alone or combined, Ultrason. Sonochem., 15, 898, 10.1016/j.ultsonch.2007.10.009 Different reducing agents were tested and the Hantzsch ester was found to be the superior reactant for this purpose. Norcross, 1962, The reduction of olefinic double bonds with dihydropyridines, J. Am. Chem. Soc., 84, 797, 10.1021/ja00864a024 Lavilla, 2002, Recent developments in the chemistry of dihydropyridines, J. Chem. Soc., Perkin Trans., 1, 1141, 10.1039/b101371h Stout, 1982, Recent advances in the chemistry of dihydropyridines, Chem. Rev., 82, 223, 10.1021/cr00048a004 Fowler, 1984, vol. 2 Liu, 2006, Selective reduction of the endocyclic double bond of 3-substituted coumarins by Hantzsch 1,4-dihydropyridine, Synthesis, 771 Gębicki, 2004, Transient species in the stepwise interconversion of NADH and NAD+, Acc. Chem. Res., 37, 379, 10.1021/ar030171j Cravotto, 2003, The reactivity of 4-hydroxycoumarin under heterogeneous high-intensity sonochemical conditions, Synthesis, 12, 1286 Mason, 2002 Cravotto, 2006, Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications, Chem. Soc. Rev., 35, 180, 10.1039/B503848K Cravotto, 2007, Forcing and controlling chemical reactions with ultrasound, Angew. Chem. Int. Ed., 46, 5476, 10.1002/anie.200701567 1998 Li, 1997 Li, 2005, Organic reactions in aqueous media with a focus on carbon−carbon bond formations: a decade update, Chem. Rev., 105, 3095, 10.1021/cr030009u Chanda, 2009, Organic Synthesis “On Water”, Chem. Rev., 109, 725, 10.1021/cr800448q Manabe, 1999, A Brønsted acid-surfactant-combined catalyst for Mannich-type reactions of aldehydes, amines, and silyl enolates in water, Synlett, 1401, 10.1055/s-1999-2871 Manabe, 2002, Dehydration reactions in water. Brønsted acid−surfactant-combined catalyst for ester, ether, thioether, and dithioacetal formation in water, J. Am. Chem. Soc., 124, 11971, 10.1021/ja026241j Aoyama, 2006, Dehydrative glycosylation in water using a Brønsted acid–surfactant-combined catalyst, Chem. Lett., 35, 238, 10.1246/cl.2006.238 Akiyama, 1999, One-pot Mannich-type reaction in water: HBF4 catalyzed condensation of aldehydes, amines, and silyl enolates for the synthesis of β-amino carbonyl compounds, Synlett, 9, 1426, 10.1055/s-1999-2872 Akiyama, 2002, Brønsted acid-catalyzed Mannich-type reactions in aqueous media, Adv. Synth. Catal., 334, 338, 10.1002/1615-4169(200206)344:3/4<338::AID-ADSC338>3.0.CO;2-O Saito, 2007, Pictet–Spengler reactions catalyzed by Brønsted acid–surfactant-combined catalyst in water or aqueous media, Tetrahedron Lett., 48, 835, 10.1016/j.tetlet.2006.11.147 Hota, 2009, A green chemical approach for the N-alkylation of aldoximes to form nitrones in organized aqueous media and their in situ cycloaddition with olefins, Green Chem., 11, 169, 10.1039/B812290C Song, 2008, Etherification in cyclohexane/DBSA/water microemulsion system, J. Mol. Cat. A: Chem., 282, 144, 10.1016/j.molcata.2007.12.003 Cravotto, 2003, The aldol reaction under high-intensity ultrasound: a novel approach to an old reaction, Eur. J. Org. Chem., 22, 4438, 10.1002/ejoc.200300369 Cravotto, 2005, The Suzuki homocoupling reaction under high-intensity ultrasound, Ultrason. Sonochem., 12, 91, 10.1016/j.ultsonch.2004.05.005 Zhang, 2005, Solvent-free mechanochemical one-pot reductive benzylizations of malononitrile and 4-methylaniline using Hantzsch 1,4-dihydropyridine as the reductant, Org. Biomol. Chem., 3, 1617, 10.1039/b502662h Zhang, 1999, Efficient Pd-catalyzed heterobenzylic cross-coupling using sulfonium salts as substrates (PhO)3P as a supporting ligand, J. Org. Chem., 64, 2796, 10.1021/jo982250s Drexhage, 1977, Dye Lasers, vol. 1 Moylan, 1994, Molecular hyperpolarizabilities of coumarin dyes, J. Phys. Chem., 98, 13513, 10.1021/j100102a014 van Staveren, 2004, Bioorganometallic Chemistry of Ferrocene, Chem. Rev., 104, 5931, 10.1021/cr0101510 Photochemical and electrochemical characterization of 8 and 4u will be described in a forthcoming communication. Appendino, 1993, Unusual course of the reaction of 4-hydroxycoumarin and aliphatic aldehydes, Helv. Chim. Acta, 76, 1194, 10.1002/hlca.19930760306 Yang, 2004, A metal-free transfer hydrogenation: organocatalytic conjugate reduction of α,β-unsaturated aldehydes, Angew. Chem. Int. Ed., 43, 6660, 10.1002/anie.200461816